Sales consulting and revenue generation strategy that helps your business scale — for founders, CROs, and revenue leaders at small and medium sized companies.
Although great salespeople and great marketers can cover up a lot of inefficiencies, building the foundation of a revenue driving organization and scaling up will often expose those inefficiencies. The simple fact is that not every seller and marketer out there is an "A" player.
This means that as companies grow they need to implement flexible processes that act as force multipliers and make the sum of their parts better than the individual contributions would be on their own. Product and vision are a big part of that, but process and operational excellence allow product and vision to meet the market.
"Process and operational excellence are what allow product and vision to meet the market."
Two decades of building and leading revenue organizations across media, adtech, fintech, edtech, and B2B data — as an operator first and an advisor second. The work is not theory; it is the set of processes that let a growing team stay on message and on the same page.
Engagements range from hourly consulting to fractional revenue leadership to defined, project based work. Every one starts with the same question: what conversation should you be having, and with whom?
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Success in market means a consistent and focused message that is not about your products or brand. It is about the immediate needs of the individuals who work for your customers. We work on customer mapping, message development, and channel strategy — the foundation of any strategic revenue plan.
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Any successful revenue organization is obsessed with training and helping all of its people become the best that they can be. We build programs that convey your organization's goals and message in a way that gives your people agency and incentive to carry that message to your clients.
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Incentive plans, organizational structures, internal tools, and even HR policies form the backbone of any incentive structure for GTM employees. Making sure those frameworks are structurally sound can be the difference between growth and stagnation.
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Dive deep and inspect the impact of your message on your target market. Work through the best way to sell your clients the bucket before you try to sell them the water that goes in the bucket.
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Creating a playbook is one of the best ways to get everyone from marketing, to sales, to client service on the same page. Built properly, the process makes your message and your processes work hand in hand.
Experience across the media and digital marketing space, including large platforms like LinkedIn, Meta, and Twitter, as well as hundreds of marketing and advertising technology companies, DSPs, publishers, agencies, and brand marketing departments.
Significant advisory experience with traditional financial service firms, as well as FinTech platforms and solutions.
Assignments in the B2B space have often focused on data leverage, technological transformation, and the use of tools to improve efficiency.
Extensive experience consulting in the EdTech space, both with startup technologies and platforms focused on student engagement and adaptive learning, as well as with more established and traditional education brands.
Brand and marketing experience covering a myriad of retail, dining, and consumer products companies.
Projects have extended into a number of industries, including energy, technology, and engineering.
Dan is an innovative collaborator who is always able to come up with strategic solutions for any business challenge. Using tech, data, and analysis, he is able to bring visionary ideas to the table. He is able to cultivate really strong partnerships tied to his solution oriented approach, and commitment to driving success for all parties. On top of that, he is kind, understanding and truly listens. Everything you want in an executive leader.
Dan is a creative and insightful strategist, and a servant leader. His presence is always one of education and enlightenment, spearheading complex customer interactions, conceiving of as-yet unconsidered directions for growth strategy — both internally and externally — and, most importantly, inspiring large teams in the collective pursuit of success.
Dan Greenberg's consistency with sharing honest, nuanced perspectives, in a professional and direct manner, has been extremely valuable to our team's planning, execution, and evaluation approaches. He seeks to understand and dial into root points quickly and fairly, and then delivers additive, high quality advice.
The Library holds the written and recorded version of the same frameworks used in client work — playbooks, courses, long-form essays, and the podcast. Buy what you need, when you need it.
Hourly consulting, fractional engagements, and project based work. Tell me where growth is getting stuck and I will come back with a point of view.
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Dan Greenberg · October 14, 2026 · 6 min read
Think about closing this way. We hear all the time that the buyer has to be the hero of the story, but we don’t often hear how to create that situation. In order to make your buyer the hero, you have to create a situation where they feel some sort of ownership over the solution. That means they have to share in the process that matches the solution with the problem, and leading them to that collaboration is your job as a seller.
In the modern business landscape, closing is not what it once was. Buyers have all the information they need and can easily see through urgency tactics that used to be effective. This means that sellers cannot close buyers, but instead need to help buyers close themselves. This is harder to do, but very effective when done well.
It is incumbent upon us as sellers to help buyers build the story of the solution for themselves. If we build it for them, they won’t trust the answer. In order to do this, we must straddle the line between exciting / interesting, and familiar / safe. This is a hard line to straddle, especially since we can’t give them the complete answer, we have to guide them and help them get there themselves.
The easiest way to conceptualize this idea is through the use of a four-piece puzzle. There are two ways to approach this four-piece puzzle, and the one you choose is dependent on the situation you are in. There are two things that can hold a buyer back from making a buying decision, either they don’t understand how the solution will get them where they want to go, or they don’t believe the value of getting there is worth the cost.
I find that sellers don’t often know which situation they are in, and therefore, what they should be addressing for the client. That part is really important. You need to know if you are addressing a solution issue or a value issue, and you can work towards that by asking the right discovery questions. Does your buyer understand the problem and are they deciding between solutions, or does your buyer still lack a full understanding of the problem and the weight of the other issues being caused by the problem?
If you are addressing a solution situation, your buyer understands three things and does not understand one thing:
There is nothing revolutionary in what I have just laid out, the problem is that we often talk about problems, we talk about solutions, and we talk about outcomes, but we don’t do a good job of putting the three together, and connecting what that implies for value. Thinking about this puzzle as your guiding star as you create agendas and presentations in the closing stages of your cycle can be very helpful. Show the client the missing piece and ask them how they want to get from problem to outcome, or how they want to fill in the empty space. That can be very powerful.
If you are addressing a value situation, your buyer understands three things and does not understand one thing:
In this scenario, laying out the three things that they know together is still very powerful, but this scenario changes the focus a bit. Now, instead of talking about how you get from problem to outcome, you are talking about all of the costs that they are currently incurring that they are not factoring into the equation: efficiency, people, systems, opportunity. All of these costs change the equation, so the answer to the puzzle here is an equation. You can set up the equation for them, and remind them of all of the costs they are not already factoring in, but you will have to let them work the equation out for themselves. Of course, you can also remind them of factors on the value side that they may not already be thinking of as well.
Each one of these visualizations allows you, the seller, to paint a picture of what your buyer currently understands by leading a conversation about three of the boxes and developing their descriptions of those three boxes. It is incredibly important to understand the exact words and descriptions used by the buyer to describe those three boxes.
Then, when it is time, a conversation about the box on the bottom right of each puzzle allows you to flesh out the buyer’s description of a perfect solution in the context of the other things that are already known. This allows you to help them complete the puzzle in their mind. The trick to these simple puzzles is that people want to discover something new, but if it looks vastly different from their current world, it will be scary. The conversation visualized in this way puts the discovery in the context of what the buyer already knows, marrying the exciting and interesting with the familiar and safe.
Whether conversationally or visually, the buyer should be the one in the driver’s seat when the puzzle is completed, but you must be the guide who decides which puzzle to complete, and in which way to do it. In fact the buyer wants you to do that. The buyer wants to feel that they understand the situation and the solutions and all of the implications at a high level, but does not want to do all the work associated with truly understanding the ins and outs of the decision. That is why you get to do that work for them, so long as you leave room for them to finish it.
If you do leave that space for them to finish, they will take ownership and closing will feel effortless.
Dan Greenberg · October 1, 2026 · 7 min read
You must be willing to ask hard questions and you have to be willing to lose the deal. Pace, persistence, and bravery are very important in sales, and the lack of any of the three can adversely affect your deals. If you don’t move conversations forward, if you don’t push buyers outside their comfort zone, and if you don’t ask hard questions, buyers will make decisions without you.
I have alluded to the concept of asking scary questions in recent articles, and I want to spend more time focused on it today. You have to be willing to ask the client what is going to cause the deal not to happen in order to put yourself in the best position to make it happen.
“What are the things that are causing a delay and making it so you can’t agree right now?”. “If you don’t end up agreeing to work with us, what would likely have caused that decision” Yes, those questions are bold, and scary, and they could bring the entire deal process to an end, but if you don’t ask them, any deal that was destined to hit a roadblock, will end up hitting that roadblock anyway, and you will spend a lot of time, resources, and energy before you learn that.
Of course, you may worry that asking these types of questions may force negative thinking and bring problems to the table that would not have ordinarily come to the surface, but any serious buyer has already confronted possible issues with a deal. Deals that have structural issues will eventually be derailed by those very issues, and the only way the issues can be fixed is by asking about, understanding, and resolving the problems. You give yourself significantly more opportunity to make a deal by surfacing potential problems. Here is how that plays out:
A. Deals with no structural issues:
B. Deals with structural issues:
It’s easy for a buyer to say that everything is great and that they are interested in buying. That means they will spin their wheels later on, and put in the hard evaluation work later. Later is easy because it is something we don’t have to deal with at the moment. But this is why pace, persistence and bravery are important in sales. Sellers must be willing to ask scary questions in order to challenge clients to really think about if they are interested or not. If a prospect is not fully engaged, they will say they are interested because that costs them nothing in the moment. However, it does cost you, the seller, a lot. That prospect will do the real evaluation and investigative work later when you are not in the room. And if that happens, you have lost your chance to be influential. That is why it is so important to directly ask scary questions in person and in the moment.
Deals that move slowly don’t happen for two potential reasons. The first reason is causally reversed and it is that the deal is moving slow because the buyer is not that interested and they are just stringing you along.
But, the second reason is important and it is one where the pace causes the problem. When a deal moves slowly, the people who were excited about it originally lose excitement, because the solution does not remain new. The risk never lessens, but the excitement abates, and you need excitement and opportunity to overcome risk. People within the buying organization start to think that maybe there is an issue with the deal, and wonder why it isn’t moving, and before you know it, you have a bunch of people on the buying side with doubts and concern about risk, and with zero excitement.
This does not mean that there is no such thing as a long sales cycle. It is not about the time from start to finish, it is about the pace. You can have a deal that takes 28 calls, 13 meetings, 142 emails, 6 demos, and 4 social outings, and takes 11 months, but the pace has to be there. It needs to move from interaction to interaction, and more importantly from topic to topic, and stage to stage. And all of this is accomplished by persistence, and by asking scary questions that engage people, and cause them to think about real answers.
When a buying organization spins their wheels, they may hit roadblocks that they don’t want to deal with. If you allow the conversation to lose momentum because of those roadblocks, there is a good chance you will lose the deal. You have to get them thinking about how they are going to make it happen in that very moment when they are interested in and excited about making it happen.
Here are some examples of questions that do that type of legwork:
These questions may seem a bit mundane, and forced, but it is the timing and the manner of the ask that is most important, not the questions themselves. When you have a buyer who has had a real opportunity to work through all potential structural issues in a deal and there is agreement and excitement to move forward, you must transition the conversation to the details around how to get the deal done, rather than the old conversation about if it is the right deal. Your job is to align your team and the buying team and create one team where the goal is to get across the finish line logistically, given the assumption that the real fundamental decision has already been made.
That transition of conversation has to happen with pace or you will lose momentum. If you are unable to make that transition, it means either, there are still outstanding fundamental issues with the deal itself, or you never had a serious buyer to start with.
Dan Greenberg · September 16, 2026 · 7 min read
I have a guilty pleasure. Well, I have more than one, but at the moment I’d like to have a little fun and talk about one of them. I really like competitive reality shows. I don’t generally like other reality shows, just the competitive ones, specifically Survivor and Big Brother. I reference these shows from time to time in my writing, which some folks will remember, and I do the same in my upcoming book and my upcoming online course.
Why do I care so much about these shows? Aside from the fact that they are entertaining to me, I see many opportunities in life to take lessons that can train us in sales and business, and this is one of them. These shows give us a unique vantage point that allows us to see life and how decisions are made from an angle not always made available to us. So much of the behavioral ability that we need in sales doubles as social skills that we use everyday in life. This means that we get to learn from everything; including pop culture.
As you are likely aware, these shows are strategy games where players get voted out one by one as the game progresses, so it is important to influence others to vote the way you want them to in order to get the right people out of the game at the right time, and to simply remain in the game yourself. The issue is that there are a dozen or more people all trying to influence each other at any given time.
The overwhelming majority of players severely lack any subtlety whatsoever. When interviewed by producers where other players cannot hear them, they talk about how good their strategy is and how they understand the game so well, and as a result they know that the best next move is to get player X out of the game. Then they return to the group, find someone who they know needs to be influenced and tell them that they “need to vote player X out of the game”, and list the reasons why. While this is a form of strategy, strategy does not mean anything if you can’t convince people to go along with it.
Most of the time what happens is that the players who feel insecure with their place in the game, at the moment of the conversation, agree to go along with the plan, and the players who feel more secure and have other ideas also agree, but then secretly work behind the first players back on another plan. So, what is going on here, and what is the takeaway?
What is going on is that the person who is told directly how to vote automatically thinks to themself, “why is this other person deciding how I vote?” If the person who was told how to vote feels secure in the game, that will cause them to dig in on their own plan even more because they now sense a formidable force that they will certainly have to deal with down the road. And if they don’t feel secure in their game, they may agree, and may even go along with the plan, but they will be incentivized to look for others to work with at the first opportunity.
So, what is the answer? Well, it’s simple but rare. It is so uncommon to see a player who has a plan ask other players what their plan is, what they are worried about most, and why they are thinking what they are thinking. If players did that more, they would know what other players’ biggest insecurities and concerns are, and could speak to those in future conversations. Also, of note is the fact that having a conversation with someone right before a vote, is always seen as trying to force an outcome, but more inquisitive conversations earlier in the cycle would be seen as more strategic and constructive.
All of the above is true when power is equal, but it is even more so when the person trying to do the persuading has more relative power. In shows like Survivor and Big Brother power can shift quickly based on the circumstances, and a person who had power one day can be the most likely to be voted out the next, while a person that had no power can sometimes find themselves being looked to by others as the outcome decider.
Oftentimes when people on these shows gain power, they become fixated on executing a very specific plan that they have envisioned, to the exclusion of all else. They find themselves in a position of power, and then falsely calculate that executing their own plan, including voting out the people that they believe threaten them, is the best way to hold on to that power. And sure, to their credit, if they did have complete control, and could make sure that the exact people they wanted to be voted out were, in fact, voted out, they might be right. But that is not how life or the game works, and there are other people with independent brains in the game. Regardless, they push forward trying to exert maximum influence on their alliance, or within their sphere of influence hoping to be able to execute perfectly on their plan.
Sometimes they get their way in the short run, and sometimes they don’t but inevitably, there comes a time when they are no longer holding power and have to rely on others. That’s how the game works, and that’s how life works.
As a player starts to develop power, they are in the perfect situation to strategically share power and democratize certain parts of the strategic decision making to other people in their sphere of influence. This can earn the person loyal supporters who trust that they are heard and valued by that person. Regardless of the presence of structures and titles, power will shift, and if a person who just found themselves in a position of power misses an opportunity to strategically share power, they will find themselves in a much worse position when they no longer hold the same level of power.
Even if they are right, and their plan is best, a suboptimal plan with buy-in from a team or a group, that is well executed, will achieve far superior results compared to an optimal plan with limited buy-in and subpar execution. Buy-in from the team actually improves results even if the plan is not perfect. It is not that people on the team all need to get their way, that is impossible, but they need to feel heard, and valued, and their ideas accounted for. If that process takes place, then the majority of people will be more bought-in to the plan and share the vision and work harder and smarter to achieve it. This will mean that even sub-optimal plans yield better results than optimal ones that are not well executed.
Basically, the point here is that creating plans and then trying to persuade people to execute the plan as you have constructed it will often lead to sub-optimal outcomes. Whether it is a project or program within your organization, or a sales process with a customer, the more your counterpart has access to real influence and feels that access, the more buy-in there is, and the more likely you are to end up with collaboration and a high level of execution.
Telling another person what to do is a form of confrontation, and that means it triggers the fight or flight response. People don’t change their mind because you tell them to. Instead, they entrench (fight), or they disengage (flight), and then do whatever they want without you. Those are the two options. So, developing conversations before the critical decision point, and allowing your counterpart to truly be heard and feel like they have an opportunity to shape and influence will help you avoid the fight, as well as the flight.
Dan Greenberg · September 3, 2026 · 6 min read
A couple of weeks ago I posted an article about what closing looks like in the new, modern business landscape. There is no discrete closing phase, and buyers don’t need information from sellers like they used to, so sellers lack leverage. More finitely understood, buyers have so much information that they know what prices they can get, when there are deals to be had, and who they can buy from so the old tactics deigned to manufacture pressure to buy just don’t work very often anymore.
The two things that do work, because they speak to our human nature are visualization and urgency. Visualization helps a buyer imagine a future where the desired outcome exists and that vision helps motivate the buyer to move the deal forward. Urgency reminds the buyer of the negatives associated with the status quo causing them to compare a solution to a problem rather than one solution to another, which is a much more favorable setting for a seller to work in.
Both visualization and the creation of urgency require a key ingredient that stands on it’s own merit and must be developed throughout the sales process. I call it, animating the enemy. In most cases, the enemy is the status quo, but it can also be an incumbent, a competitor, or an internal group at the buyer pushing back against change or progress for one reason or another. If you are the one who can help the buyer clearly paint a picture of why the enemy is a problem, and how much it costs, you will have a major leg up when it comes to your buyer picking a solution.
This concept so important and yet no one coaches to it. Sales managers, trainers and coaches like to talk a lot about making the buyer the protagonist, or the hero of their own story. But we forget that every hero and every story needs an antagonist.
A story where the problem is no big deal, and can be solved over time by incremental steps, is just not that compelling. It won’t motivate anyone to act.
They only way to tell a compelling story is to animate the enemy in a way that calls for a hero to act. But we, as sellers, dont focus nearly enough on creating and animating a tangible enemy.
Without an enemy it is also not a very fair fight. We are trying to pitch our solution and they end up comparing something vs. “nothing”. “Something” is scary but “nothing” is not scary. “Something” comes with risks while no one gets blamed if “nothing” goes wrong because it already existed and no decision was made. It is always easier to stick with the status quo unless the status quo itself is scary, and carries risk with it.
As sellers, we must learn to animate the enemy.
Good discovery should be designed around learning what is hard and bad so it can become part of the animation of the enemy. Don’t use discovery to learn what they like about your products. Use discovery to learn what they don’t like and what is scary about their current situation.
Of course, what I just said is aided by everything else you do in a sales cycle. You need to have done great discovery to have the tools to do this. You need to have handled objections well, and you need to have moved through the process in a prosocial way that has developed trust with the client.
If your discovery was properly executed, and you properly drew out objections and handled them in a way that builds trust, you should have worked through a lot of explanations of the problem that should tell you how to detail out and describe the antagonist in a way that helps your protagonist visualize it. Even if there are no deadlines or time constraints for the buyer, the simple existence of a well described antagonist can help them understand the need for quick change. If their answer to your question about timing is something like, “as quickly as possible”, that sounds great, but it means nothing, and will not help you close a deal. Work with your buyer to establish a goal date so that you can work backwards and set a calendar that you can both work off of. That is urgency that must be developed throughout the process and cannot be manufactured at the end of a deal cycle. And, the only way that urgency can be developed is if there is an enemy that needs to be escaped from.
Once you get to the end phase of a deal cycle, things change a bit. Deals don’t close on their own, so you have to be resilient and dedicated to pushing forward. Don’t spend your time on the deals that are not likely to close, but when you pick one to work on, don’t let up. Develop many relationships across the buying organization, and it is important to touch base with all of them and work through these processes so that when they all come together internally everyone feels comfortable.
Buyers, and especially C-Suite buyers, care about risk and loss. Sure, they like efficiency and growth, but uncertainty, risk, and loss of principal are much much worse than limited growth. Uncertainty is potential risk, and if they are not comfortable in the understanding that the risk level of making a choice is very low, they just won’t move. So, be aware that while your individual stakeholders need to understand the risk of the status quo, your C-Level executives need to understand the lack of risk associated with what is new compared to that status quo risk.
Without an enemy, your buyer can visualize an outcome where they want to end up and they can even feel some urgency to get there, but if they are not running away from something, other priorities will overshadow that urgency and the vision will fade. The only way to reinforce your ability to have a real closing conversation with your buyer is the enemy they need to escape.
Dan Greenberg · August 19, 2026 · 9 min read
The modern business landscape has changed significantly over the past decade, and I have written extensively on that in other articles. For now, suffice it to say that there are two main reasons, which both come down to social dynamics and affect the balance between buyers and sellers in the same way, namely; buyers don’t need sellers for the same things they used to. They don’t need them for the obvious things, so only sellers who can work with buyers on the less obvious needs will be successful persuaders. The two major changes are as follows:
Closing is no longer a discrete stage in a sales process, in fact there are no more discrete stages like discovery, and negotiation, and closing. All stages happen at once, so the skills that it takes to sell are much more evenly distributed throughout the process. You are closing from day one, just like you are negotiating, discovering, and objection handling from day one. So, all of this said, what are the components that drive the close itself?
There are two major concepts that I want to talk about when it comes to closing, visualization and urgency. It’s not so much that these two things will help drive deals to happen faster, it is that without them, the deal won’t even happen. Don’t get me wrong, a seller can get lucky, and the client can actually have urgency that they are very aware of, and the client can also do their own visualizing. But in those situations the seller just got lucky, and didn’t really have influence on the close. What I want to discuss here is how to develop these two concepts for a buyer.
Visualization:
There are four questions listed above and they are in a specific order for a specific reason. This line of questioning, asked at the right time can trigger your client to start to think about what it would be like for the team to actually start using your solution. Visualization is a very powerful tool, and as soon as your client starts to visualize, their brain will automatically start to work on justifications to help that visualization come to fruition.
This set of questions is meant to be asked at the point in time where there are no more obvious, real objections coming from the client, and after you feel that you and the client are in complete agreement on their problem, their need to solve the problem, and the value that solve will provide. Not just agreement some of those things; agreement on all of them. As mentioned above, there is no finite start to the closing phase, but it is important for a seller to understand when the problem has been fully fleshed out, and when the client completely understands the outcomes, value, and solutions. Once that point arrives, and there are no more substantive objections, then closing becomes the objective.
There are two visualization questions in the set of four. The first asks the client to visualize what a world looks like in which the solution is being used. This is a tougher visualization because it is a state of reality, more than a tangible situation, but it is still important. The second visualization question is more concrete and asks the manager to think about their team and how the solution will benefit their day-to-day. Before each of the questions, there are buy-in questions. You are making sure that the client tells you verbally that you two are on the same page. This gives you license to ask the more intrusive, and mentally burdensome question about visualization.
Obviously, the wording in these questions needs to be changed based on each individual situation and relationship. It will also be easier to ask visualization questions if you sell a physical product, like a machine part, but there is always a user, and and always a business benefit to ask about, regardless of the type of solution, otherwise your company would not be in business.
Urgency:
Urgency cannot be created out of thin air. But you can build urgency if there’s a need, and if you have been working to develop it throughout the process. If you try to push urgency at the end it will come off as a sales tactic, but if you had been developing an understanding of lost value with the given status quo, or loss being directly caused by the status quo from the beginning, you can use that spark to light the urgency fire when it is needed.
There are two questions listed above and I have placed them in the order they are in for a reason. The first one is a bit more blunt and forceful and should be used at some point as you move toward a close. However, it can elicit a reaction that displays reluctance on the part of the buyer. Notice that I purposefully used the word “a” instead of “our” because I did not want to tell the buyer that I had decided for them that they were going with our solution. The question does leave their decision as to choice open, but it asks when they want to be able to get started with implementation.
If they show a heavy amount of reluctance, you may still have an objection hanging out there that you have not dealt with, so it is important to ask directly, and the way to do that is something like; “let me ask you this, if you decide against our solution, what is the likeliest reason you will make that choice?” If they give you a substantive reason, you can say: “great, that is exactly why I asked that questions, I sensed that there was still something that we had not covered completely and now we get the chance to dive deeper into that and see if the solution fits all of your needs or not.” At this point you can launch back into your normal way of dealing with objections. You now have the second question above in your back pocket for later in the conversation. If you did a good job at discovery throughout the process, you should have something that creates some sort of deadline or timeframe for them. You can note it and then ask about the early stages of the process in a much lighter weight way than before.
The second question is designed to let the client feel like they just have to dip a toe in the water. There is no problem with taking the first few steps, like getting the procurement process up and running, or having the implementation team meet the tech team on the buying side. These are small steps, but remind the client that if they may eventually want to move forward, it is important to set a timeline, and start with the first small steps in order to meet their time dependencies, even if they end up deciding against the deal later.
The questions above are bullet pointed, not numbered because they are not a sequence. Both need to be asked at the right time. If you have been developing an understanding of the urgency all throughout the sales process, these questions will build on what you already know and have talked about. They are designed to get the buyer to state their own urgency so that you can reinforce it. If you clumsily and obviously lead them their, you become a biased shill and not a trusted advisor.
Throughout the sales cycle you need to work to peel back the onion, understand the real problems behind the problems, and who they affect. Then, you need to be developing a value based assessment of the pain and the value of the future state outcome to the business. Once you and the client agree on all of the above and you can both state it in a succinct way, then the urgency conversation transitions to understanding who is affected, and who needs to be in the room to come to a consensus.
Sales and closing have become harder because buyers know more, are more guarded, and expect more from sellers. But long known concepts used to build relationships and drive decisions still work, they just have to be executed differently for the world we now live in.
Dan Greenberg · August 6, 2026 · 9 min read
The landscape of the business world has fundamentally changed, and it has changed because the way we interact with one another socially has changed. Sure, technology has had a big impact on this, but fundamentally, the difference is social and relational.
Two main changes have fundamentally reshaped how buyers and sellers interact. Buyers’ needs have shifted; what they require from sellers is now less urgent and more ambiguous. That has caused the demands of the seller in the sales cycle to change significantly. Let’s take a look at the two most vivid changes:
These two stark reality changes, as well as others, have made the job of sales harder. But companies still buy solutions, and the sales are still there to be made, the only question is, can you be influential in that decision making process.
The changing landscape has made the shape and trajectory of the sales cycle unrecognizable to sellers from 20 years ago who have not adapted, and one of the biggest changes has been the traditional understanding of the concept of closing and how that does or does not affect a deal. Sellers no longer know how to drive urgency because driving urgency has gotten much harder and sellers have not adapted new tactics.
There are managers and trainers out there who remember that one great close they had where the customer said “no”, and they just would not take no for an answer, and eventually they dramatically turned things around, or where they put pressure on the client to close right before the end of the quarter to help the team make quota. Sometimes these memories are exacerbated, and sometimes they are very real. Sometimes they happened a long time ago, before information was as readily available, and before switching accelerated, and sometimes they occurred recently and just happened to work out with a needy client being in the right place at the right time. But the key thing to realize about them is that they are not scalable. Making one deal like that is possible, making deals over and over again like that is just not a reality anymore.
The reason is because all of those tactics required pressure and driving urgency, but in the new landscape of information availability and easy switching those tactics are ineffective because buyers don’t need sellers to purchase a solution, they only need them where there is true consultation value being offered. That can dramatically lengthen sales cycles, and introduce uncertainty and lack of control into a sales organization’s processes.
Company leaders consistently talk about their top performers as being almost mythical. These leaders glorify these one-off dramatic closes, and the salespeople who made them happen. But for the really good sellers, it took them a long time to build up to their success, even if it was the most recent close that made everyone else notice. More importantly, the skills that make great sellers great at their job have very little to do with the dramatic closes that get all the attention.
Companies put pressure on new sellers to perform in the same way as these mythical, magical closers, but it just does not work like that. Small companies looking to hire often talk about how they have one great performer and everyone else that they hire doesn’t perform as well. This is simply a margin problem. The top performer is performing well because they have built up to that point, and because when they started there was likely significantly more low hanging fruit, that the original top performer has since closed, so a new seller will rarely perform as well at the margin until they are given time, often years.
I worked at the company formerly known as Twitter for over 4 years early in my career. It was a great place to work in some ways, but it had its faults. They hired great, and intelligent people, but they suffered from a culture that I have only gained an understanding of as my career has progressed. They consistently talked about culture and mission. They talked about doing what is right for the client, and being truly consultative. They talked about not being the typical salesperson, and supporting the great things that the company is doing for the world. Of course, this was all said at company-wide and organizational meetings. But then, in 1 on 1s and small group meetings, the conversation was very different. It sounded like every other sales organization. Why is your pipeline lagging? Are you going to hit your goal this quarter? Why are your weekly call numbers so low? These questions are not bad in a vacuum, but the discontent was palpable for sellers.
Great sellers develop trust over time, and quarterly goals can have a directly negative effect on that progress. Actually, let me rephrase, it’s not the goals that are the problem, it’s the threat of dismissal for less tenured sellers if they don’t hit those goals. Goals can be arbitrary, and rarely reflect a fair understanding of what should happen. If a seller decides to take a long term approach to a book of business and has a real plan to succeed, then missing a goal in early quarters is not necessarily a bad thing. Sure, they should not get commission for deals they don’t close but internal urgency can have a direct and negative effect on long term success of sellers. The core idea here is that short term expectations often have negative effects on the long term ability of sellers to grow and become great.
Jim Collins popularized the understanding of The Stockdale Paradox in his book, “Good to Great”, which happens to be an excellent business read, and I highly recommend it for sellers. The Paradox is also discussed in Viktor Frankl’s psychology book centered around the Holocaust, “Man’s Search For Meaning”. The Stockdale Paradox is centered around James Stockdale, a Naval Officer who was taken captive as a POW by the Viet Cong, along with a number of other soldiers, for years. I, by no means want to compare POWs to sales, as the former is about humanity and truly matters and the latter is not and does not, but still, the underlying message is enlightening.
Stockdale and the other men were kept in terrible conditions and with no access to the outside world. It was easy to lose hope, and allow yourself to go mad, which could easily be deadly in those situations. The soldiers who were pessimistic, and did not believe they would survive oftentimes did lose their minds or do things that put themselves and others at risk. On the other hand, the soldiers that were incredibly optimistic, and believed that they would be home by Thanksgiving, or by Christmas, were often bitterly disappointed when their expectations or hopes were not met, and many suffered similar fates to the pessimists.
The soldiers who fared best, and gave themselves and others the best chance to survive, and many did, were the ones who balanced optimism with realism. The way they did this was by truly believing that they would survive and get out, but never placing any time based prediction, or expectations on their belief. Optimism says, “Yes, I can get through this”, or ,“I can accomplish this”. Realism says, “There are many factors that I cannot control no matter how skilled or smart I am, and therefore I will take things one day at a time, one hour at a time, one action at a time, and just keep moving in the right direction until I get there, regardless of if I know now, when that will be”.
This type of thinking just isn’t conducive with monthly and quarterly goals. Don’t get me wrong, I get it. Goals have to exist, and sellers should not be paid variable income when they don’t produce. The trick is for sellers and managers to come together and build a long term strategy that is optimistic and realistic so that the seller understands their responsibility and the plan to fulfill it. Revenue organizations need to allow those processes to play out and support the long term growth of their organization and their sellers, and that means understanding that short term results can, and are often negatively correlated with long term success.
Dan Greenberg · July 16, 2026 · 9 min read
Sales are not negotiations, and negotiations are not sales, and you can be a perfectly good seller without being a great negotiator. However, it can’t hurt to be better at getting the specific deal you want. More to the point, many of the skills that great negotiators learn double as excellent skills for sellers.
Although you could spend years studying negotiation and learning how to handle individual situations, I would like to give you a bit of a cliff notes version of the topic specifically focusing on negotiation skills for sellers. I would like to do this with the help of three books, a good amount of summarizing, a bit of melding of ideas, and some color of my own.
The first book I’d like to reference is “Negotiation Genius” by Deepak Malhotra and Max Bazerman. Side note: I have had the pleasure of attending seminars on negotiation by Malhotra, as well, and he uses the sound of his wedding ring clanging against surfaces to get attention, and for emphasis, better than anyone I have come across.
“Negotiation Genius” is an excellent and clear read, and I highly recommend it. It focuses on the science and information of a negotiation as well as the preparation. It works the reader through theories on information imbalances, incentives, acceptable outcome agreement, and I guess the best way to put it is, the geometry of a deal. This means that there are two dimensional areas that contain potential deal outcomes and dictate where the deal can end up across the plain of potential outcomes.
The three most important points that I would urge a reader to think about when it comes to this writing, are as follows:
The second book that I would like to discuss is a book that I have referenced before in my writings. It is called “Start With No”, and it encompasses the ideas of Jim Camp, and is written by Robert Jordan. This book is as much a sales book as it is a negotiation book. I highly recommend it. The book talks about power dynamics in negotiations, and how to build consensus, working backwards from a place where consensus cannot happen. There is really one key takeaway from this book, and it is as follows:
The last work I would like to call attention to on the topic is “You Can Negotiate Anything” by Herb Cohen. Cohen talks about three paradigms that exist within a negotiation that many negotiators don’t spend enough time thinking about how to leverage. Here are the main ideas.
Human beings are mentally lazy when it comes to most things in the business world because we are evolutionarily, and naturally trained to disregard most stimuli in order to focus as much of our finite mental and physical energy as possible on only the things that are vital to our survival and advancement as people. Basically, this means that we do not engage with things that demand mental energy exertion. This is important because a willing negotiation adversary has to be able to at least consider things from your point of view and more importantly, believe that you are considering things from theirs. For this reason, driving true engagement is the hallmark of a great negotiator and the hallmark of a great seller.
This means that skills like speaking in the terms of the buyer, displaying empathy, and understanding of the problem, repeatedly going back to the problem, social proof, and focusing on outcomes and value over solutions are all key to successful negotiations for the same reasons that they are key to successful sales.
In addition to these skills there are a few things that you may have noticed as themes across all three of the books that we discussed.
One last note that is particularly important for sellers. Sell the vision, not the price point. The more you talk about price, the worse the outcome will be for you. All sales are inherently trades. You give them a solution, and they give you money. Conceptually, the money they give you has about the same value as the solution you give them. If the conversation is constantly about the thing they are giving you, and never about the thing you are giving them, the scrutiny will all be going in one direction. Remember that they have the problem that needs solving, and you have other clients that have the same problem. There are only a few ways to get your solution, but many avenues to find clients who have similar problems. Reframe and go back to selling the outcome and the value whenever you get stuck in a pricing conversation prematurely.
Dan Greenberg · July 1, 2026 · 7 min read
When you reemphasize a point over and over, you may concerned that you are repeating yourself but it will not feel that way to the listener. Your client or prospect does not know your material as well as you do, so as they process the message, it will take time for them to integrate your message into their thinking. Time and repetition are the only things that can help that integration process. The time part is up to them; they will only think about what you are saying as much as they want to. The repetition part is up to you.
Beyond this, your listener cannot take in too much material. If you try to explain too many concepts, or ideas, or processes, they will not take them all in. If you attempt to get too much across, your message will get muddied, and you will lose impact.
There are a number of well known, and almost universally accepted studies that have been executed in the psychology and behavior science world which support this assertion.
The original Dilution Effect study done by psychologists Richard E. Nisbett, Henry Zukier, and Ronald E. Lemley in 1981 showed convincingly that adding less relevant, or mediocre information to an otherwise strong case causes the receiver to temper their opinion. In other words people were less convinced when mediocre points were added on to a strong case.
A more recent study from 2024 published in Scientific Reports explicitly tested whether more arguments are better than a single argument. The study found that exposing listeners to weaker supporting arguments along with a strong main argument reduced the overall persuasive effect of the strong argument. This study essentially shows us that our brains average arguments together instead of adding them on top of one another.
What does all of this mean? It means that trying to make many points or arguments dilutes focus by weighing down strong arguments, and by pulling attention from the main point. Your buyers just simply won’t take in that much information. And even if they do, the additional information they take in will likely detract from the point you were trying to make.
There is one simple device that can be used to help you keep focus as you prepare presentations, and this device also helps your clients internalize and integrate your main message. The method laid out below is often attributed to Aristotle, but he almost certainly did not say it, although it does conform to his argumentative and rhetorical style.
Tell them what you are going to tell them: Tease out the information you are going to provide at a high level, and inject some mystery and excitement by explaining your point at a high level while leaving gaps in the details.
Tell them: This is the only part that most people already do. This is the core of the presentation, and the time when you fill in most of the detail gaps, but not all, as you still want to leave some mystery. The trick here is to stick to the main points of focus and not expand scope.
Tell them what you told them: Again, here it is important not to expand scope. The object in this third iteration of your main argument is to contextualize the same points you have already made and make sure they are understandable, digestible, agreed upon, and actionable for next steps.
You will notice that there are three steps to the above method, and that is not a coincidence. There is something about the number three. It pains me significantly to talk about this because, much to the annoyance of my wife, family, and friends, I am quite OCD, definitely in the social and colloquial sense, and almost certainly in the medical sense as well, and one matter of obsession for me is the number four, and more generally, even numbers. Even numbers make sense to me, and make things seem complete and in order, and beyond that, I just like the number four. I would like everything to be, and happen, in fours.
All of that said, there is magic in the number three. Three is the number that establishes a pattern. We find this in storytelling as old as the written word, and we find this in law, and legal texts, including the Talmud dating back thousands of years; the Bible, think three wise men, and the Trinity; and in more recent social and cultural touchstones including stories and fairy tales like Goldilocks and The Three Bears, and The Three Little Pigs and the recurring theme of three wishes when a genie lamp is found. The number three is also used consistently in humor and joke construction. The formula goes; something happens; then a pattern is established; then the third occurrence is the punchline. Our brains recognize the number three as something special, and of note.
Two is not enough to establish a pattern, and four is too much to remember easily. People can easily remember three things, and at the same time don’t consider the satisfaction of three criteria or components to be mere happenstance. This is why it is a good idea to pick no more and no less than three points that you would like your buyer to take away from your interaction or presentation. Repeat those three things over and over again, and make sure that the focus stays there. Tell them the three things you are going to tell them about, then tell them the three things, and then tell them about the three things you told them about.
Repetition is important. Let me repeat. Repetition is important. In presentations and meetings, it is indispensable. Your client will not get bored by what you are saying, they likely won’t even notice it, and they definitely won’t think it’s weird. They aren’t paying as close attention to you as you think or would like. They have not heard your content as many times as you, so it is new for them. And, they don’t understand all the things you are telling them, so hearing things for a second and third time helps their brain ingest and integrate the thinking that will help them complete their solution puzzle for themselves.
The high level framing of your information at the beginning of a presentation allows the client to prepare their brain to take in the subject matter. The high level framing of your information at the end allows them to reflect on it within the context of verything they have heard. Select the information that you really want to drive home and find ways to say it in interesting and captivating ways. Cover less, and go deeper. It is even okay to call out repetition, and note that the reason you are doing it is due to how important the point is. This will work as a signal to the client to listen. It is also okay to state outright what you want the client to leave the conversation understanding. This is another signal to pay greater attention.
It can be scary to leave out information. You may worry that the piece of information you have left out is the one compelling thing that would have convinced your buyer. However, if you try to share too much information you may end up diluting conversations and failing to resonate with all of your buyers. Focus on your most compelling arguments, build a story around them, and repeat those points over and over… and over, so that your listener has the ability to integrate your information into the way they think.
Dan Greenberg · June 17, 2026 · 10 min read
It is not always clear that long term relationships trump transactional quick wins. But, as a business community, we had a really good macro example recently that can help us understand the value of good long term relationships. In tumultuous and uncertain times, it becomes very clear that deep and solid long term relationships are very helpful for your business.
Often these tumultuous times are idiosyncratic and affect only one or a few relationships at a time, but for many businesses, when the COVID pandemic and lockdowns hit, all of their clients and relationships were affected. Uncertainty is a constant, but the more uncertain things become the more a solid relationship and foundation matter. The trust and foundation of the relationship allows you to work through problems with the client together. When times are tumultuous, business leaders look for trusted advisors, and the only way that you will be considered one is if you were working towards that type of relationship long before it became a necessity.
As most of us have been forced to confront in the past two to three years, the baseline reality around us is starting to feel more and more like a consistent crisis. Uncertainty levels are so high that buyers are acting in ways previously only seen during external shocks and crises. The business landscape is changing drastically; as information becomes more ubiquitous, and AI changes the way that software is built and relationships are managed, switching costs for buyers are decreasing over time. Pay as you go models, as well, as modular and specialized solutions are fragmenting formerly cohesive industries and solution sets. This means that new logos are not as valuable as they once were. Why? Because they can much more easily leave you. In the past, the costs associated with switching vendors were much higher than they are today.
This means that the incremental dollar; the lowest hanging fruit, the next easiest place to earn or defend a dollar is becoming more of an indicator of where to spend time, as a business, as opposed to the old answer which was often to get new logos and then service them. This means that the job of client success, account management, relationship management, and sales, is merging.
The functions are becoming more and more similar in what they demand, and that demand is to build solid foundations and grow long term relationships. Unifying these functions gives organizations the ability to focus resources and time on driving the next dollar as opposed to artificially valuing one set of dollars over another. And, when driving that next dollar is the organizational goal, long term relationship building becomes important for every individual in the organization.
This does not mean that everyone in a revenue organization has to be good at closing deals or technical account management. There are still different functions and different people can fulfill them, but the revenue organization, as a whole, has a much more uniform task across client cohorts.
The traditional selling motion, when it comes to building long term relationships, consists of many small sales. This means that a seller has to consistently work towards small commitments, get those commitments, and then fulfill what they said they were going to do before asking for the next commitment. In a similar way, account managers need to work hard to make sure that clients are fulfilled in what they are trying to accomplish before asking for the next commitment, which is often more data, or insight, or additional relationships that can help them expand more within the client business.
The difference between the two is that account managers / client success managers have a more tangible output that they can point to, ie. the product and its results, than do sellers. Account managers are also usually less incentivized to ask difficult questions and reinvest in discovery and problem definition, but oftentimes have more of an ability to do so, and more upside since the client has already committed, and needs them to help get the results they paid for. The bottom line is that long sales cycles and long term relationships both consist of consistent fulfillment, discovery, and micro-commitment asks. They are rinse and repeat cycles.
There is a story that circulated the client relationship world, at least in the west coast tech scene about 10 years ago. It is possibly apocryphal, and I cannot vouch for its origins, but it is almost certainly based in reality, and there is certainly something to be learned from it.
The story goes that Bloomberg, which sells investment focused insights and data, mostly to investors through terminal seat access, had a slight product defect that was causing users to have to take a number of extra steps to download a certain report and most could not figure out how to do it. This particular report was an important report that most clients needed, and so, most clients resorted to calling, emailing, or putting time on the calendar of their account manager every time they needed the report. At one particular all-hands the product team announced that they had finally figured out a fix, and would be rolling it out that quarter, which would allow clients to download the report without taking up the time of their account manager, and more importantly, without the annoyance of the client. The product team expected jubilation from the account management team, but the reaction was the opposite. The account management team implored them not to release the fix because, as they explained, fixing that problem for the clients gives us the opportunity to interact with our clients and ask them questions. Most of these clients are busy and resistant to setting aside time to talk to us, and the expressions of thanks and acknowledgments we get for fixing the problem allow us the license to speak with those clients and have more detailed conversations about their businesses.
Client success managers and sellers should solve their clients’ problems, but they should not solve their problems and then move on as if the job has been well done. Whenever something is accomplished, whether it be a usage problem, a product fix, a conversational agreement, or an advancement in the sales process, that mutual accomplishment should be used as a jumping off point for a new round of discovery, micro commitment asks, and future fulfillment.
Keep in mind however, that you should not fall victim to empty continuances. We all know what empty continuances feel like in social settings. They are the other person appeasing you without really committing to anything in the future. They sound like, “oh ya, sure, we should pick a weekend to get together in a couple of months, let’s figure it out when it gets closer”, in the social world, and they sound like “oh ya, we should set another meeting on the calendar to discuss this further, but I have to run to a meeting so lets email about it”, in the business world. Don’t get fooled by these and assume they mean anything. You either need to push harder and get another micro-commitment, or decide that the client just isn’t that into you, and spend your time elsewhere.
Another common problem in long term relationship building is when sellers or account managers get stuck with a single relationship on the buying clients side. Even if this person is a champion of the product or the deal, and even if they don’t leave the company or team, they may have limited organizational power, and when things stall, having only one relationship is a very bad thing.
This is a problem that good client partners are solving long before it develops into a problem. Every time you have a demo or a meeting set up, you should be sending multiple LinkedIn messages and emails, yes both, to a number of different people within the org that you have contact information for. You should let them know that you will be discussing problems and solutions that have to do with their line of business and that you would love to get their perspective on the situation and goals. Of course, if you don’t know the person yet, you can also just express a desire to put a face to a name and get to know them since you have started to work with others in their organization.
During meetings and demos, call out individual people by name and ask them relevant questions that pertain to their function and business line. Ask select stakeholders if they are onboard with the agenda and objectives personally so that more people feel buy-in with your process. Ask them what is most important to them, and evaluate their reactions. Are they confused? Excited? Bored? This will help you follow up.
After meetings and demos take the time to send individual notes to key participants that you want to continue to have a relationship with. Thank them for their time, and ask them if they got what they had hoped for out of the meeting and if there is anything else they want to discuss. Give them prompts of things you think they may be interested in to make the response easy. Also, if the meeting was recorded, it’s always a good idea to listen or watch so that you can look for and listen for cues that will help you with communication strategies for each individual.
It’s great to have an internal champion at a buying organization, but if you only have one, you can find yourself in a tough situation if the deal stalls, or if something happens to change your relationship, or if that person leaves the company. The more key people you can have relationships with, the better.
Long term relationships are slow to build because trust takes time, you simply cannot rush them, if you try to, the foundation will not be real, and they will crumble when they are needed most. It is important to be methodical, and always think about what the next step in relationship growth is and how to achieve it.
Most sellers make the mistake of selling right away, and many account managers make the mistake of never selling. Building a long term relationship means learning now, and selling later on. Throughout the entire lifecycle of a client there are opportunities to sell, but there are also opportunities to prioritize relationship growth, win micro-commitments, and position your organization as a partner and as an indispensable advisor to their business.
Dan Greenberg · June 3, 2026 · 6 min read
There are essentially two types of interactions in the course of a sales process.
Switch points are dangerous because they allow the buyer to reset the frame and assume the comfortable and familiar position of all-knowing-judge who is there to evaluate you against other vendors. In my article two weeks ago, called “Switch Points” I talked about the perils of switching between these two interaction types in a single setting and a bit about how to think about those switches. In this article we will inspect the transition itself and explore more tactical strategies for dealing with a reality that most sellers find themselves in during most client interactions, whether they realize it or not.
The problem, as I see it, is that sales people rarely think about the difference between these types of interactions, and even more rarely think about which one they should execute relative to the goals they are trying to accomplish. If you need to do heavy discovery, learn about the clients business, or get to know the client, or their business, or their company, or their process, it makes sense to plan for a more informal, conversational interaction. However, if your goals are more transactional, or the need is to position your solutions, or commercially teach the client, or demo your product, or to instigate a negotiation, it will make sense to plan for a more formal presentation, or similar type of interaction.
The ultimate aim when thinking through your goals and interaction types is to avoid switch points, and to select a type of interaction that suits your goals. However, the choice is not always yours, and it is not always easy to establish enough control to dictate the setting and meeting type, so in addition to thinking about the type of meeting you want to have, it is also important to define and execute strategies for confronting switch points when they inevitably occur.
The issue you will have with a conversation-only interaction is that buyers often push for a presentation, especially early in the relationship. The formal presentation-style meeting helps them impose the frame that they feel comfortable with; you as the vendor, and they as the judge. In order to pull off a conversation-only interaction, you will need to telegraph the plan well in advance and get buy-in from the client before the meeting is scheduled, otherwise they will expect you to present, and their expectation will likely cause your ‘conversation-only’ plan to feel forced and awkward if you stay true to it. Otherwise, you will have the option to abort it, and present, but that will be less likely to accomplish your goals for the interaction. In short, it is easier to schedule presentations, but in order for presentations to be successful, we need to have conversations, and clients don’t want to talk to us, and have conversations, especially early in the relationship.
If you noticed above, many of the goals mentioned that call for a conversational-type meeting are goals that generally need to be accomplished early in a sales cycle, as opposed to many of the goals that call for a presentation, which are generally goals that need to be accomplished later in the sales cycle. However, in order for a seller to gather the information they need and to build rapport, relationships and credibility with the buyer that would make for very successful presentations, social and conversational interactions are vital. This is the conundrum that all good sellers find themselves in early in a sales cycle. We need conversations, but we have not yet earned the right to have them, and buyers want presentations because they feel more comfortable in those settings.
There are essentially three ways to combat this conundrum:
None of these strategies is fool proof, but if executed well, all three can give you, the seller, the opportunity spend time on insights, problems, and desired outcomes for the buyer early in the sales cycle, which will help you accomplish the goals that you need to accomplish in order to be able to set the table for the more advanced stages of the sales process where the focus will be on more transactional interactions, solutions positioning, your commercially viable teaching, more in depth and targeted demos, working sessions, and detailed negotiations.
Dan Greenberg · May 20, 2026 · 10 min read
I have written about switch points in the past, usually in the context of control, and how to keep it and leverage it. I want to take some time here to specifically focus on switch points and why they are so dangerous for the seller when it comes to the seller’s ability to remain in control of interactions.
First, let’s define “switch points” since it is a term I made up, and I want to make sure to be clear about what I am talking about. Switch points are those times in a sales or business interaction where the tone, or demeanor, or feeling of the meeting changes, usually from less formal to more formal, and the expectation for the next phase of the meeting becomes much more about structure and presentation. Every salesperson reading this knows what I am talking about. You just exchanged pleasentries and had a five minute casual conversation with a few people on the client side that covered their business, more generally, and some of their concerns with the status quo. Now, everyone has finally arrived and taken their seats and the alpha on the client side looks at you and says, “So, you have some slides to present, right?”
Some version of this is very common, but the situation is also a sneaky and insidious trap that can lead to a number of bad outcomes. There are other versions of switch points; simply switching from discovery to presentation, or even from pleasantries on a cold call to the substance of the call. Regardless of the exact nature of it, at the switch point, the client switches from active conversational partner to receiver of information. Consciously or not, they want to position themselves as the receiver so that they can be in control. They become the all knowing judge, who has control of the money, and control of the decision. Where does that leave you, the seller? You are the presenter, the one who needs the money, the one who is being judged. And, what happens when the dynamics of the interaction change in this way?
I’ll tell you what happens; you LOSE all the power.
Before the switch, the power was equal. You needed money and the client had a problem and needed your solution. You were talking like equals. After the switch, you are presenting to them, and you need them to make a favorable decision in order to get the money that they have. You are no longer talking about a thing they need (your solution) and a thing you need (money), you are now talking about a thing they are judging the viability of (your presentation), and a thing you need (money). That is a very different situation.
Many switch points happen early in interactions so the first 10 minutes of any meeting are very challenging. Not only are most of the challenges to your power and control usually attempted early on, but you also usually come across the switch points in these early stages.
Whenever possible it is best to stay in active and equal discussions with your prospect and avoid any potential switch points. If you never have to present, and the entire meeting is completely conversational, and evolves naturally from social conversation to a discussion of problems and ideal outcomes, then you win. You never had to switch, and you were able to do a lot of discovery, a lot of relationship building and align yourself with the client in mutual pursuit of the answer. But this is just not feasible much of the time.
In most cases, you have asked for the buyer’s time, and the buyer has an expectation of some kind of presentation of your solutions so it becomes socially and behaviorally untenable to deny that reality. In these cases, you have to switch. You have to switch from social to business, or you have to switch from conversation to presentation, or you simply have to switch from standing and discussing pleasantries, to sitting and discussing their situation and problems. If the situation you are in calls for a switch, it is not a good idea to fight it. If the meeting progresses with your desired agenda, and noticeable resistance to your deviation from what is situationally acceptable, you will lose control quickly. The buyer wants you to present so that they can assume their comfortable role as the all knowing judge who gets to evaluate you against your competitors, so resistance can lead to awkwardness, and even potentially relationship resistance and animosity. It is good to know when you will have to switch so that you can own it, and do it in a way that preserves as much control as possible.
The first thing that is important is to lead the transition from small talk, or social activity to the business conversation. You don’t want the client to suggest it, because then you will be following their lead, and that is a signal to the whole room that you are not in control. Look for language and body language clues from the client that they are ready to get started and preemptively state something like, “I’m sure we all have packed schedules today, I certainly do, so I want to respect your time and talk through the agenda so we can get down to business and discuss what we need to”. Notice that you have done a few important things with this statement. You have led the conversation and kept control. You have also framed yourself as a prize by stating that you have other things going on that day and don’t have all day for this client. However, at the same time, you have shown respect for their busy schedules and time, and put the client and yourself on equal ground. You have framed the steps of the meeting, and insinuated that you can come to agreement on the agenda and then cover all of the important matters. This is assumptive, but you have not made any assumptions about how they will feel at the end of it all; those can come off as heavy handed, and cause the client to feel trapped.
After you have made this proactive statement, you then have the opportunity to set the objective and the agenda. It is a good idea to get them both on the table at once because if either are agreed to, you can converse about bringing the other in line with the point of agreement. Laying out the objective and the agenda, and including how long the meeting will take, shows that you have a plan for the meeting, and will inspire fewer challenges to your control.
After the objective and agenda it is important to tell the client what the next steps are, and what the decision at the end of the meeting will be. Say something like “OK, so once we cover all of those topics, it should be pretty clear to all of us if it makes sense to get the solutions engineers on our side together with the implementation engineers on your side to evaluate the technical part of the process”.
Lastly, get buy in. Make sure everyone is on the same page about the objective, the agenda, and the next steps decision. This is one of those scenarios where you are giving up control to get more control. Did you happen to watch James Holzhauer play Jeopardy? He always worked hard to find a daily double square about 15–20 clues into the game at which point he would always bet all of the money he accumulated on the 15 to 20 clues before it. If something went wrong (rare as that reality was), he still had 40–45 clues remaining in the game to make up for losing all his money. If he got daily doubles later in games, he often bet a much smaller percentage of his money (unless he was already so far ahead that it didn’t matter), because he had much less time to recover if something were to go wrong later in the game.
The “Holzhauer strategy” is the key here. If there is going to be a problem, get to it early in the meeting. This is the time to ask the completely open ended questions and let the client tell you if the objective, the agenda, and the next steps don’t make sense. You don’t want this challenge coming up at the end of the meeting when you are trying to solidify next steps because if it does come up then, you likely won’t recover. If this does happen at the end of the meeting, the buyer will say something like, “Well, looks like we have more to work through and we can’t really come to a decision on that now, but we can discuss it more later”. Translation; “We are not on the same page, and there is no need for me to continue this process because that meeting was a waste of my time and I don’t see us getting to the right place anyway”.
The idea of getting everything out on the table early in the meeting is really important here because it allows you space. Once you have voluntarily ceded control to a person or persons of your choosing, the real decision maker or makers on the other side of the table, and you all come to an agreement on objective, agenda, and next steps, then it becomes significantly harder for you to lose control later in the meeting, since they have already agreed to your terms, and steps. Then it just becomes about you executing and keeping things on track, both in terms of topics, and timing.
This also allows you to pose the next steps conversation in a much more closed manner as the meeting is wrapping up. Since you have already established buy-in and agreement, it makes it much harder for the client to move the finish line at the end of the meeting without looking bad or paying a social cost. This means that when you are rehashing next steps at the end of the meeting, you can be very assumptive about the plan for the next meeting, and buy-in that you secured early on. Sure, you have to ask for it one more time, but it can be a closed question that really only calls for a ‘yes’ or ‘no’ answer, and you can simply lay out the terms as an exact repetition of what was agreed upon at the very beginning of the meeting.
Focusing on the first 10 minutes of a meeting and formulating a clear plan for how to deal with switch points can have major and positive effects on your ability to attain, retain, and maintain control in sales settings. And, so long as you have control, your job becomes infinitely easier and much more likely to be a success.
Dan Greenberg · May 6, 2026 · 8 min read
Many look down on mimicry as fake or deserving of rebuke. We have terms in our culture, colloquially used, like poser, which assign a very low level of respect to those who imitate others, or act in ways that are perceived to be copied from others’ actions. And yet, mimicry is one of the most basic, and useful human actions. Evolutionarily, we use it to seek like individuals and feel socially and physically secure. Being a part of a group is one of the most basic human needs. The fundamental building blocks of how we evaluate group membership are partially built on behavior and appearance. This may offend our modern social and cultural sensibilities, because it weighs appearance and superficial action very highly, and can easily be seen as a form of racial or cultural bias, but none of that changes the fact that it is part of our shared human nature.
Culturally, we also look down upon undesirable bias, and rightfully so. However, similar to mimicry, it is one of the most natural human behaviors to be attracted to, and to like people who look and act like us. It helps us be assured that we are normal and accepted socially and physically. Let’s look past appearance for a moment, and focus on behaviors and actions. It is not unreasonable for someone to judge a counterpart based on their ability to act in accordance with the social cues and behavioral norms of the environment that they are in.
Inevitably, each one of us gives off signals as to what we perceive as acceptable social behavior in each of the social settings that we find ourselves in. Regardless of the level of moral standing of your buyer, it is human nature for them to judge you and how well you fit into those social boundaries that they perceive. So, this makes it incumbent upon the seller to be aware of the behaviors of the buyer, and what those behaviors say about the expectations. Of course, at that point, the decision as to adherence level is completely a personal decision for the buyer, but being aware of the cues and the fact that it is a decision is important.
More to the point, mimicry, and other forms of conforming to social cues are not negatives, in and of themselves. Matching tone, cadence, volume, and excitement level are basic social skills that allow your counterpart, in a business setting, to feel comfortable and make it more likely that the relationship will be developed in a mutually beneficial way. The burden of this recognition and action usually falls on the seller because the buyer is usually thinking more about if they even want to engage than trying to think about advancing the relationship. If we focus on individualism and negative outlooks rather than matching the energy and tone of our counterpart we are shunning basic human nature and making relationship development much tougher.
It is worth it to think about mimicry, tone matching, and energy matching in business settings, and how they can influence relationships and deals. When people are given information that is meant to be repeated, we always make changes to the wording even if what we end up saying has virtually the same meaning as what we were told to say. If you look out for this in the real world, you will notice it, but there is a great example of it in pop-culture; specifically the TV show “Impractical Jokers”. First of all, it is a hilarious show, especially seasons 1–7, but more to the point, it illustrates the interesting balance that people attempt to walk when trying to navigate social situations. The premise of the show is that three comedians sit behind the camera and through an earpiece dictate to the fourth comedian what they are required to say and do in candid real world settings in front of the camera. The fourth comedian, who is operating in the world (other than the hidden cameras), is fed embarrassing or uncomfortable lines and actions, and is required to do and say them. Almost every line that is fed to the fourth comedian is then said in the real world setting, but almost without fail, the fourth comedian doctors the line in a way that changes the words but not the meaning.
The doctoring of the words accomplishes nothing in regards to the predicament they find themselves in. The things they end up saying are still extremely embarrassing and uncomfortable, the only thing that is changed through doctoring words is the feeling of ownership and control of the words being said. Think about that for a moment. These people are being put in horrifically embarrassing situations and even though they can’t change that reality, they still take one basic step, which is make sure they aren’t directly mimicking someone else.
The point of all of this is that we have a viscerally negative reaction to direct mimicry, and yet, it is basic human nature to attempt to fit in by showing that we are alike. The aversion could have to do with control and ownership, and it could have to do with authority, but whatever the contributing factors, we as humans have a deep and foundational aversion to precise and direct mimicry. On the other hand, we conform to societal norms, and go to great lengths to fit in through behavior that is similar to the group we want to be part of.
Like many things in life, we are searching for a balance. If we make it obvious that we are parroting back or deliberately trying to act like our counterpart it becomes undesired behavior and can quickly sour a relationship. But subtle mimicry, tone matching, and energy matching tells our counterpart that we are similar to them, and that brings a feeling of comfort which can create a fast track to trust and relationship building. The bottom line is that if we focus too much on individualism, and our unique way of doing things and interacting, we will not be taking into account how our body language, and behaviors can influence others.
Former FBI Supervisor Joe Navarro wrote an excellent book that I highly recommend called “What EveryBODY Is Saying”. In the book he takes the reader on a tour of the entire human body from head to toe, literally, discussing body language cues and tips to help a listener understand what that speaker is saying beyond the words that are being said. One of the biggest takeaways from the book is that we, as humans, tend to be very good at hiding, or betraying our true emotions with our face because we have a lot of practice doing it, so oftentimes the best signals that one can use to gauge another human being beyond their words come from other parts of their body.
The bottom line is that much of our communication is non-verbal. We have heard this line of reasoning before, but how many of us take the time to think about what that means for our calls, and our presentations, and our meetings. Most of the time we spend preparing for client interactions revolves around what we will say, and what we will show the client. But a very small portion of what the client will remember from the interaction will have anything to do with what we say or show.
Your clients’ lasting impression of your interaction will be stored in their brain and associated with a feeling. The negativity or positivity of that feeling will be determined by their comfort level with you, their assessment of how well you performed socially, and their level of comfort with you as a part of their network. These assessments will be made using a bit of what you said, but mostly how you and your body behaved during your interaction. That includes similar speech patterns and subtle mimicry. It includes signals of openness and comfort in your body language, and maybe most importantly, it includes the level of synchronization felt by the client which is heavily influenced by tone and energy matching. Disregarding these signals disregards our most basic human nature, but taking these signals into account can give you a much better chance to build rapport, and drive relationships forward.
Dan Greenberg · April 22, 2026 · 8 min read
We have all come across sellers whose optimism is nauseating. They are always about to close the biggest sale yet. They project monster deals, and they consistently talk about how they will “crush their number”. Sometimes they do, and sometimes they don’t but the frustrating thing about these people, for managers and leadership, is that they make it very hard to forecast. Managers have to build in systems, and checks in order to counterbalance the optimism and relay realistic forecasts. The overly-optimistic do tend to attract real belief in their ability to perform, but they are not seen as savvy when it comes to the business, and they have a hard time advancing in the organization.
The other side of the coin is not the pessimists. Pessimists frustrate people with their lack of belief, and they cause similar problems from a forecasting perspective because they underestimate their numbers. There are not really upsides to the pessimist, and they usually don’t last long in revenue organizations. The other side of the coin is actually the realist. The realist is perceived as having a lack of belief because they tend to predict lower projections than managers expect, but their projections tend to be closer to the truth, and their understanding of potential blockers and headwinds is usually understood to be savvy. So, while they do not tend to inspire that high level of belief, they do tend to be seen as sound organizational players who understand the business.
So, the question is which should you tend towards? The sandbagging realist, or the head-in-the-clouds optimist. The realist will often be called a pessimist because they under-forecast, but they are often much closer to the actual results than the optimist.
What makes things so hard for the realist is that it is in the realist’s nature to only project revenue that they can see a path to. The problem is that we cannot see a path to all of the revenue that we can expect to bring in over the course of a quarter or a year. We just simply have not had all of the right conversations yet. If we only projected revenue that we could see, our projections would be pretty low and we would not inspire much growth in ourselves or interest from those around us.
The problem for the optimist on the other hand, is that they assume that every deal that is in their pipeline is likely to close. They actually have the same problem as the realist but viewed through a different lens. Like the realist, they cannot see what is not in front of them. They cannot see the reason why they are likely to lose any deal in their pipeline, so they assume they won’t. For this reason they are certain that many of their deals will close, and they end up over projecting.
Past pipeline delta is a great way for organizations to temper forecasts and end up with better projections. What I mean by this is a specific multiplier for a specific seller, or set of sellers, that takes into account past projection to performance deltas. It is not always easy to do correctly, but the right multipliers applied to the right situations, for the right sellers, can help to improve projections at an individual and organizational level.
That said, getting back to the individual. It is OK to start from either point of view. If every deal in your pipeline is likely to close, you have to figure out a way to sprinkle in healthy realism that introduces possible pitfalls and headwinds, and allows you to discount your forecasts, but more importantly, become vigilant against possible problems. However, if you can’t possibly think of a world in which unlikely or unknown deals could possibly close, it is important to figure out a way to introduce a business development, or new opportunity coefficient into your calculations so that you can correct your forecasts to a more growth oriented level, and more importantly, redirect some resources and mindset to those potential opportunities which will make them more likely to manifest themselves. Predictability is very important to leadership so accurate forecasting raises your profile and value within any organization.
The idea here is that you can start from your natural personality and mindset, but having self awareness, and knowing yourself very well, allows you to introduce checks and balances in your own mind that will help you forecast better, but also make you a better seller, and alert you to the right ways to spend your time and resources. It is not easy to find this balance, and not everyone will find it in the same way, but it is important.
Now let’s go one level deeper here, and think about how optimistic or pessimistic we should be about our prospects for success as a seller. It is estimated that Cynthia Erivo and Ariana Grande each made around $15M for their role in the production of Wicked For Good last year alone, while the average performer or actor is waiting tables, working towards membership points in their union, and trying to scrounge together enough money to pay rent. Patrick Mahomes is projected to make well over $200M in salary alone over the course of his likely 15 plus year career, as quarterback for Kansas City Chiefs, while the average NFL player will play for about 3 seasons and make about $3M, in total. This may seem like a lot of money, and it is, but remember that they have trained their entire life for the job, and will likely find themselves physically unhealthy, and somewhere around 26 years old without the skill sets necessary to excel in other fields. And all of that does not even take into account the average Football player who never made it to the NFL, and was never paid to play.
Are Cynthia Erivo and Ariana Grande 50 or 100 times better than the average highly trained singer, dancer and actor out there? Is Patrick Mahomes, or any top athlete 75 times better than the average player in their sport, or hundreds of times better than highly trained top collegiate athletes who never made it to the NFL? Absolutely not. Sure they may have a unique quality about them. They may perform the right role, or play the right position, at the right moment in time. They may work harder, although there are only so many hours in a day, so that effect can likely only be incremental. But, they are certainly not 50, 75, or 100 times better than the other highly trained and talented individuals they compete against. So, why do they make 50, 75, or 100 times more money than those other people?
Tiger Woods, at his peak, only shot 2–3 strokes better than average tour golfers at most tournaments. That’s about 4% better. Top CEOs, absent external factors, can expect to drive a company’s CAP table growth to somewhere around 7% in a great year, while average CEOs can expect something more modest, like 4% or 5%.
The sellers who are making $300K or half a million, or even a few that are making over a million per year; they are not 10 times better than the average seller. They have learned to do the little things better, and they have learned to become so consistent at those little things that they are now second nature. Of all of your suspects, a small percentage become prospects, and of your prospects, a small percentage become leads, and of your leads, a small percentage become opportunities, and of your opportunities, a small percentage become deals. This may sound depressing, but it is exactly the opposite. It is exhilarating. It means that we just have to move the needle slightly at a few strategic points in our funnel to change our outcomes drastically. If you are closing deals with 2% of your prospects, and you change that number to 4%, you just doubled your revenue to goal and your commission.
The high earning sellers out there are not more talented, and they don’t know something that you don’t. They don’t have a special personality or demeanor, and they are not born with an ability to handle rejection that you don’t have. They have simply improved over time. They have committed to learning from setbacks and they have made a commitment to themselves to get better each day, which adds up over the years. Unlike in sports or on Broadway, there are not only 32 NFL teams with a handful of top paid players each. There are not only 41 Broadway theaters that funnel hit performances to movie production studios with a few highly paid leads at any given time. There are thousands of companies who need to hire millions of sellers.
The sellers who are outperforming and out earning everyone else have trained themselves to control their emotions. They have learned to really listen. They have coached themselves to be attuned to social cues and to recognize what drives emotion and engagement. And most importantly, they have developed, in themselves, the discipline to set routines, and systems and to stick to them. That is all. We all have reason to be optimistic.
Dan Greenberg · April 7, 2026 · 7 min read
Lets talk about neuromarketing and its implications for sellers. Sounds nerdy, and technical, or maybe a bit pseudo-sciency, I know. But, the field of neuromarketing has done extensive work on the mindset of buyers and how they perceive and make decisions regarding ad messaging, packaging, and customer experience. Consumers at scale provide the advantage of producing a lot of data, so it is much easier to study mass consumer purchasing, and then apply it to sales and business buyers. Many of the lessons from consumer buying are transferable when thinking about buyers in a sales setting. And yes, they are even transferable in a B2B buying setting. Why? Because human brains are human brains, and because people buy from people.
Well upwards of 90% of the decisions a buyer makes are not within the realm of that person’s conscious decision making. This can mean entire purchase decisions when we are thinking about consumers, but for B2B buyers, it is things like how much they like a presentation, or how happy they were with dinner after the meeting. Because of this, thinking about the messaging, the packaging of that message, and the buyer experience are incredibly important when addressing that part of the buyer’s mind.
Buyers want to feel like they have a grasp on everything but just need a bit of help to complete the “puzzle”. If you introduce too much to them, and they subconsciously feel like the problem is too broad or they need to learn too much to grasp the breadth of it, they will shut down and instead gravitate towards a problem that is easier to solve. Extensive studies have been done on choice architecture and the amount of choice that supermarkets should give buyers when it comes to driving the highest likelihood of a purchase of certain products. The answer is essentially that buyers want agency, and want to feel like they have a real choice, but as soon as you introduce too many options, the decision becomes unwieldy and overwhelming and the likelihood of a purchase drops significantly.
If we bring this into a B2B sales setting it sounds more like this. If we introduce zero or very little choice into a sales process, our buyers will be unlikely to engage in a serious way, either because they will feel uninterested in the problem, since there is no puzzle to solve, or because they will feel constrained by the fact that they have no agency and no real choice in the matter. Basically, if they have no choice, they will head for the hills because they don’t want to be controlled, and if the problem is not interesting to them and they feel as if they already understand the puzzle, then there will be no interest or engagement because there is nothing to solve, so they will zone out and think about a problem that is intellectually stimulating to satisfy the part of their brain that is conditioned to be goal oriented. If, on the other hand, too many choices are introduced, or there is ambiguity or lack of definition in the choices, the client will feel overwhelmed. They will decide that the problem is too hard to solve and they will devote their mental energy to another problem that satisfies their brain’s desire to find a solvable problem and solve it.
People love puzzles. They want them to be hard, and they want to feel accomplished once they have solved them, but they want them to feel solvable. They want them to fit nicely within their current understanding of the world so that solving them does not cause them to have to alter their relationship with reality.
It is our job as sellers to find the balance. We can’t overcomplicate the matter, but we must say something that highlights a problem that needs to be solved. That problem must be able to be solved by something that the client does not already fully comprehend, but is within the realm of the boundaries of the understanding which they already possess. In other words, we must talk in terms that are comfortable for the client and create a paradigm that encompasses both the current state and the desired outcome, but at the same time, there must be movement and evolution in the client’s understanding. Think of your client as a cat. If the string is sitting still on the table, they won’t care at all, but as soon as the string starts to move, they will want to pounce on it. Human brains are interested in things that change and move, as well as things that need to be figured out. Both of those can be used to your advantage.
One of the most effective methods I have used to create a comfortable and solvable puzzle for my clients is a four-box matrix. I often build this matrix for myself in order to visualize how I want to lead the client through the conversation:
Walking a client through the 4 part puzzle can be tricky because it is easy to want to jump in and give answers, but allowing the discovery, and the conversation to develop, and therefore allowing the client to solve the problem themselves will put you in the best position to win the deal. Neuromarketing focuses mostly on consumers who are making decisions in the absence of sellers. That can teach us something. As sellers, we need to create an environment where our buyers can make decisions, not tell them the answers or try to make the decisions for them. So, what is the recipe for doing that?
As you lead the client through the puzzle; be concise, be clear, be interesting, be uncluttered. This focus and attention to the most vivid but direct points will drive the conversation in the right direction.
As you start to observe your client putting pieces together and truly engaging; find excitement, find humor, find simplicity, find comfort. This emotional injection will help the client feel in control, and at the same time, like they have a project that needs to be completed.
As you think about how to drive your client to the right conclusions; use active verbs, use direct words, use verbal images, use stories. This type of speech will help reinforce that there is a clear path to a desired outcome and that you are confident in how to guide them there.
Throughout the process be conscious of the fact that you always have to; tap into emotion, tap into hardship, tap into human connections, tap into yearning. These connections to human emotion and human relationships will keep you and your buyer aligned and connected.
Dan Greenberg · March 19, 2026 · 9 min read
I once had the opportunity to work with a guy named Rob. Well, I didn’t really work with him so much as watch him dance circles around me and the entire rest of our sales team. He wasn’t naturally charming or handsome, and he wasn’t particularly intelligent or a force of will when he walked into a room. Additionally, his clients didn’t really like him all that much. I mean, most of them didn’t dislike him, but he wasn’t out to make friends, and it was clear that people weren’t buying from him because they wanted to hang out with him more.
There was nothing that you could pinpoint about him that was a traditional trait or behavior of a great seller, but he constantly won. He constantly made deals happen. There was nothing flashy or interesting about the deals he won, he just won a lot of them and he was consistent. What was it about Rob that made this happen? Or, should I say, what was it about Rob that drove these outcomes over and over again? I’ll tell you the answer that I came to understand from watching him interact with clients, and I’ll preface it by telling you that after I developed this understanding of what he was doing, I heard Rob describe his success a few different times to different groups and he identified the same key driver and talked about it in the same way. So, what was it?
Rob did not need your business. It was very clear to every one of Rob’s prospects and clients that if he did not get their business, he would not be bothered in the slightest, and he would turn around and get business from someone else.
The questions that remain are, why is this core principle so powerful? And, how did he pull it off?
Let’s start with the why. Why is lack of neediness so important:
Now, let’s discuss how Rob pulled it off:
Here is the thing about Rob that is important to wrap your mind around if you are a revenue leader. There just aren’t that many Robs out there. It is a sliding scale and there are people across different parts of the scale, but in my experience about one out of every 20 experienced sellers works in a similar way to Rob. Even if your are great at hiring and incredibly patient, you won’t be able to wait around long enough and make enough good decisions to hire only Robs.
This means that somewhere around 19 out of every 20 of your sellers are not going to do the things they need to do to produce this way. They are not going to develop a big enough pipeline to feel truly like they are not in need. They are not going to harness the skills and behaviors to be able to tell clients what needs to be said in order to drive the right actions, and they are not going to develop the chutzpah to challenge clients and converse in the blunt and straightforward way that they need to. In short, they will act needy. Not all the time, but sometimes, and that is enough. It’s enough to diminish results and it is enough to put you in a position where your sellers are not performing at the level you want.
So, why is this something that leaders need to know and not the sellers themselves? Of course, the sellers do need to know it, but the number one tool in the toolkit that can make sellers feel less needy is their pipeline and they need your help to fill it. Organizations and revenue leaders need to put sellers in a position where they do not need any of their prospects or clients. You, as a leader, need to put your sellers in a position where they have so many leads and such a big pipeline that they are overwhelmed and they naturally start to act as if they don’t care about any one deal more than the others. And, you need to do it now.
Every client or prospect that a needy seller talks to is a client or prospect that is no more likely to close as a win for you than to close as a win for any other competitor with slightly needy sellers. The sooner your sellers have a great pipeline, the sooner they will start to behave like they do, and the sooner they will start closing at a higher rate.
You need to do it by using AI tools, sales development reps, marketing, and operational support to drive more leads than your sellers know what to do with. You can’t ask the sellers to do it themselves, or expect them to do it on their own. You and your organization need to make it happen, and here is why:
Dan Greenberg · March 5, 2026 · 7 min read
The conversation around AI that is dominating news and social media is all about how many of our jobs can already be done by AI. We see posts and articles about the increased power of AI its ability to do most white collar jobs. The only question is how quickly will it be able to do all of our jobs, right?
However, speaking with consultants and business services providers who work with technology companies you will hear something interesting. That conversation referenced above is outdated. It’s an old conversation. That conversation about AI being able to do everything is dominating our feeds and news cycles, but the tech forward companies that have embraced AI already had that conversation in 2024. It’s old news now. The companies who know best how to use AI have already moved on to a different conversation when it comes to their own internal operations, and it may not be the conversation you think. The new conversation is about understanding the limitations of AI and what those limitations mean for the types of people that they need to employ, the arrangements by which to employ them, and the operational rigor that it will take for humans to work alongside AI.
I am not claiming that jobs wont be replaced by technology, they absolutely will be, but I am arguing that new roles and work arrangements will replace them. This is not a new theory and there is nothing novel about my claim, but it certainly pushes back against the grain of the current flow of writing and conversation. What I am talking about here is not so much a theory, but more of a point of view. It is a point of view that matches what we have seen in history with other technological leaps, and a point of view that has already come to fruition in our current cycle in certain contexts, as companies that have promised over and over again that they will replace people with AI agents have continuously been unable to do so in many cases. And, let me be clear, and I will expound on this a bit later; it’s not that the technology can’t do the jobs, it’s that the scalability of the tools based on the technology is fundamentally lacking.
Even if you disagree with my point of view, the question is; what do you do now? As a business, how do you build for a future where technology increasingly takes over the tasks that humans are doing today, while still accomplishing everything you need to from a business operations perspective today? How do you prepare for a future where humans do different jobs while understanding that the business tools based on the technology have limitations and that means that advancement to that future state will be slower than expected? How do you act in this time of limbo?
Some think that the answer is a universal basic income or some other version of wealth distribution because eventually the machines will be able to do all the work. They have essentially thrown in the towel on business productivity, and have moved on from the economic implications. But this fundamentally misses the point. This question is much bigger than capitalism vs. socialism, or wealth distribution vs. work retraining programs. The question is; how do we stay productive as a society? How do we build organizations that embrace technology and position people alongside technology in a way that improves productivity?
There are two important things to consider when thinking through this question:
Specialization of Focus: It is not efficient to have highly skilled workers focus on outward productivity and inward tool engagement at the same time. In other words, if you have someone who is great at building relationships, you don’t want them also spending their time learning how best to interact with AI tools so that they can essentially run all of their own operations. First of all, not many people are great at both of those things but secondly, and most importantly, it’s not efficient. You want to find people who are great at doing the things AI can’t do and then pay them to do those things. Then you want to find people who are great at operating, and great at engaging with and working with tools, and pay them to do that.
Shift to the Vanguard: Businesses compete at the vanguard of technological development. We have seen this affect play out repeatedly over the course of economic history. The U.S went from being a manufacturing economy to a service economy because technology improved and many pieces of the manufacturing puzzle because commoditized. This meant that everyone could do them, so businesses started to compete on service offerings, and consultancies entered the market to help firms operate more efficiently and grow based on new financial and operational strategies. Competition fundamentally changed because what businesses competed on in the past became commoditized and that opened up opportunities for new kinds of competition, new kinds of services, and new types of roles and businesses at the vanguard of technology.
All of that said, businesses still have to offer something to the market, so there will still be production, revenue, and administration. I focus on revenue so that is what I am going to write about here but the principals actually apply quite well across an organization.
In order to prepare a business for the future while still positioning it for success today, companies need to find 3 things, and then do a fourth. Here is what they are.
Tools are function specific and since we are integrating tools into our org chart in this new agentic world we live in, we need to start thinking about how to orient ourselves based on function, not based on traditional organizational structures. Sure, some of this will look familiar, but many functions within organizations today have highly varied functions and use different tools to achieve their goals.
We are on the precipice of new ways of working, new ways to engage workers, new kinds of roles, and new ways that companies will compete. In order to meet those challenges now and in the future, we need more flexible organizational structures that are focused more on function and less on horizontal alignment. We need more decentralized power and a focus on integration of people and tools in the organizational structure. And, we need to reinvent the middle operational layer of talent in a way that allows us to hire and train the right people to interface with tools so that we can empower all of our people and tools across the org to specialize in what they do best.
Dan Greenberg · February 19, 2026 · 10 min read
We exist in the era of the buyer. Never before have buyers had so much access to information. While an abundance of data can lead to information overload, savvy, investigative buyers can now independently research the details they once relied on sellers to provide in order to become informed about products. This may seem like an old and boring story, after all, we are in the age of AI, and what we are talking about here was the information age. However, buyers en masse have been adapting to the new world of information availability and it has taken time for them to build new ways of doing things into their day-to-day activities. We are only now seeing the full effects of the internet information age play out in how buyers relate to sellers. And, yes, it is just in time for the age of AI.
Due to these technology improvements and the mass digitization and adoption of technology in business over the past 30 years, switching vendors and providers has become much easier. This reality is even more so in the software world where switching can be as simple as signing a new contract and running some internal trainings. Of course, vendors work hard to become more sticky, and to integrate themselves into the systems of the businesses they sell to, but nevertheless, switching costs are lower than they ever have been, and are especially so in software.
So, what does the fact that customers know everything, and can switch easily mean for selling organizations?
We will talk about both of those components in more detail, but first I’d like to reference the book “Customer Success”, written by Nick Mehta, Dan Steinman, and Lincoln Murphy. In the book they discuss the evolution of the Customer Success function from non-existence to necessity in some firms, as well as the foundations and practices that lead to successful customer success organizations. I recommend the read because it provides a good understanding of how the customer landscape has changed and the reason for the growth in necessity of Customer Success teams; a direct response to the changes in customers and their capabilities over time. While the book is fairly prescriptive, and very practical throughout, it does also speak to the high level landscape that sales organizations find themselves in. There are many customer centric sales and account management related learnings that can be gleaned from an understanding of the landscape.
The new reality that we find ourselves in, due to customer knowledge and low switching costs, leads to two realities for sellers and sales organizations that I mentioned above.
Let’s first take a look at the idea that customer success is a vital function for a growth organization. As businesses become more digitally reliant and more technologically focused when it comes to core operations, switching vendors is easy, but more importantly, there is no incentive for companies to become overly reliant on any one particular tool or vendor relationship. If a buying organization finds a better offer, or a better product, it feels less risky than ever before to switch to that product whenever they want. So, buying organizations go to some lengths to negotiate breakable contracts, light integrations, and test and learn approaches that allow for maximal flexibility. This reality puts the responsibility directly on the growth organization’s account team to work with existing clients and expand the value they get out of their solutions. Being sticky requires that your clients recognize value in product use, and integrate those products into the core of how they do business. The understanding of client goals, followed by the recognition of value has to come first, but once it does, selling in that deeper level of integration is every bit as much of a sales task as the original sale was.
Many organizations divide sales tasks between sellers and client success or account management, but that does not make the function of those account management and client success teams any less of a sales function. So, whether you are a seller or not, learning about goals, working with clients to recognize value and then selling a deeper level of integration is a selling function.
Client Success teams and account management teams are actually in a better situation to sell than sellers. For starters, new business sellers don’t have a working product and results that they can point to in order to help earn credibility, and maybe more importantly, client organizations have to share goals and needs with customer success reps in order to get the help they need. The problem is that many organizations do not reinforce the idea that post sales is pre sales. A customer success person’s job is not to listen to issues and solve problems, it is to be constantly running discovery, and understanding not what the client needs, but why they need it, so that they can open up additional conversations and cross-sell, upsell, and drive deeper integration.
Most customer success organization leaders will tell you that they operate with a focus on discovery and upsell activities, but if you listen to a call and hear an account manager solve a problem for their client, you will often realize that the focus is on customer service, not framing, and growth. Your best clients are your current clients, and yet most organizations don’t operate with that understanding. Firms that have already bought from you are more likely to buy more, and buy again. Every solved problem is a missed opportunity. I am by no means saying that problems should not be solved, but discovery is the most important of the tasks.
The second idea that I want to take a look at is the idea that new business is not as valuable, relative to existing business, as it used to be. Most companies operate with a goal of making as much money as possible. When a lot of money comes through the door, shareholders like it, employees like it, and management likes it. The thing about money is that it is completely fungible, so no dollar is inherently more valuable than any other dollar. Sure, it may be sexier to close a brand new deal with a brand new client who has never spent a penny before, but their first dollar is worth exactly the same amount to the company as the next dollar spent by the company’s oldest customer. By the same token, if that new client has a bad experience and leaves, the opportunity cost of that missed revenue is exactly as valuable as the opportunity cost associated with upsell dollars not driven because of a lack of focus on existing clients. The clients who have already spent money with your company, and already integrated you into their systems are far and away the most likely to spend more money with you. Why? It’s simple. They have already proven they are willing to do so.
In a world where switching costs are high, and switching is hard, and in a world where information is hard to come by, new business is very valuable because new clients tend to stay, since they can’t easily find information about your competitors, and switching is hard and expensive. But we don’t exist in that world anymore, so new business is simply not as valuable as it used to be. Any client can leave at any point, and the most likely clients to leave are the ones who are newest since your solutions are not fully integrated into their operations, and since onboarding is a relatively tricky period of time in the client relationship. This means that the long term value of a new client may look like a big number, but when weighted properly to account for churn, it gets much smaller. This means that training customer success and account management teams to onboard, and to consistently treat post sales and pre-sales so that they can farm new revenue from existing clients becomes every bit as important a sales function as what we have traditionally considered sales up till now. Client Success and account management teams should be trained like sellers, and incentivized like sellers, and sellers should remain focused on existing business and think about new dollars from old clients as every bit as valuable as new dollars from new clients.
Sure, there are times when it is strategically important to build a bigger base of clients, and other times when it is strategically important to focus on retention, but on the whole, new business is just not as valuable as it used to be relative to the whole.
The authors of the book “Customer Success” make a number of great arguments for both the importance of a top down organizational focus on client success, and the rethinking of the way that customer success teams are developed. But they also talk about the structure of organizations that best supports good customer success practices, and they recommend a Chief Customer Officer, or a Head of Customer Success who is on the same level as the Chief Revenue Officer or Head of Sales and can promote the development and fulfillment of resources for the Customer Success team. This is the one area where I think they have missed the mark. As barriers to competition continue to get lower and adoption and switching get easier the lines are more and more blurred between new and existing business. This means that Customer Success should not be a standalone function, but rather a seamless part of the revenue organization. Sales should no longer be thought of as driving new business. The function should include relationship managers and client success managers and it should be thought of as driving new dollars, from whatever source makes the most sense for the given moment.
A client who is not spending currently, but who is sold on value prop, and needs guidance on how implementation will affect their business, needs a person who we would typically categorize as an account manager. At the same time, an existing client who tested the solution and is likely to churn, needs a person who we would traditionally categorize as a seller. Sales and Customer Success need to be in one organization so that they have one overall goal. Find the next dollar. All dollars are worth the same. Hunters and farmers can and should work together and go where they are needed most to close that next dollar if they are incentivized properly, and work together in one organization.
Dan Greenberg · February 4, 2026 · 5 min read
I have referenced The Challenger Sale and The Challenger Customer a few times in my writings because Brent Adamson & Matthew Dixon do a very nice job of thinking about the way in which buyers perceive what sellers are doing, and how that influences behavior. The Challenger Sale focuses more on seller behaviors and how buyers react to those behaviors while The Challenger Customer focuses on the buying organization and how the personalities and behaviors of individuals in the organizations can affect deal outcomes.
The Challenger Customer, specifically, does a really nice job talking about the different types of buyers within a buying organization. The book spends time talking about what types of individuals we should spend time trying to influence and what types of individuals will monopolize our time and make it harder to succeed. It talks about how to build consensus, and unite individuals, while thinking about the different buyer types, and maybe most importantly, it talks about the importance of insights, and how to use insights to increase your own value and stature within the buying organization.
All of that information is highly valuable, and I strongly recommend both books. For the purposes of today’s writing, I would like to key in on the idea of buying personalities and how to address different types, and I would like to do it through the lens of Brian Tracy’s book, The Psychology of Selling. In it, Tracy works through the personality types that double as buyer types and he discusses how these types of individuals should be handled.
Understanding what drives and motivates your buyer as a human being separate from their organization can help you identify and speak to the right set of incentives, but even if you don’t fully understand your buyer, simply thinking about things from your buyers perspective will help you resonate more with them. For that reason I recommend the book, and the general practice of considering your buyer’s point of view as often as possible throughout a sales process. Tracy lays out the 5 most common types of buyers that a seller comes across, and I have summarized and paraphrased them here with some of my own thoughts:
1. Apathetic buyer — The apathetic buyer is apathetic because they have been cheated or let down before. They will see let downs as a constant in their lives, because they will consider the lack of delivery up to their high level of expectations as a form of being cheated. For this reason, they won’t buy. This does not mean they will never buy anything, but their level of skepticism and cynicism is so strong that their past experience will trump any ability to form a relationship or have a productive dialogue. It is very hard to influence people like this, so most of their purchase decisions will happen as a result of timing and happenstance, and sellers will have little ability to influence them, and should therefore seek out other individuals within organizations or other organizations to work with.
2. Analytical buyer — The analytical buyer wants to know every single detail, fact, and piece of information before buying. For some this is a way to protect themselves internally from backlash if the decision goes poorly. For others, this is just how their brain works, and it is part of their modus operandi. It is smart to be wary of these buyers because sometimes they will go through the motions without intending to buy, but those who have serious conversations and also want facts and details can be good partners.
3. Relationship oriented buyer — The relationship oriented buyer wants to know how your solution will affect people. This buyer needs to feel very comfortable with the seller, and needs to respect and trust the seller before the real dealings can begin. This buyer will care about the current processes that the internal teams are experiencing and how those can be improved, as well as if there will be any negative effects or externalities as a result of implementation of your solution.
4. Entrepreneurial buyer — The entrepreneurial buyer is Tracy’s version of what we often call the alpha. These buyers need pertinent facts quickly, and want to make a quick decision and move on. If they judge your understanding of what is pertinent and what is not to be in line with theirs, they will trust you and move quickly. However, if your conversations lack relevance or do not get to the point, they will be quick to move on from you.
5. Self actualizing buyer — The self actualizing buyer already knows what they want, and will buy right away if you have it. They are the researchers, and good students of the bunch who know as much as you do about your products, and a lot about their competitors as well. Understanding why they want what they want is the key to opening up conversations with these buyers; if you can open them up, they will want to learn, and will be open to real and productive conversations.
Tracy’s classifications are an excellent guide, and I hope I have done them justice in my very abbreviated summaries. However, the point is not to adhere to his definitions and prescriptions at all costs. The point is to think about how you classify your buyers. Think about what they care about, and how they prioritize their needs, and work towards a proactive effort to be relevant, prepared, and action oriented with each individual you interact with.
Dan Greenberg · January 21, 2026 · 10 min read
Many economic theorists and thinkers spend their life working on marketplace design and trying to understand the most efficient ways to design markets. What they focus on, for the most part, is maximizing the utility. The interesting thing about this is that only a buyer or a seller ever make a decision about a purchase because no single actor is both buyer and seller at the same time. In order to have a successful business, you must have a market of buyers, and in order to make a purchase, there must be a product created by a seller. The economic theorist is a figment of the imagination. In other words, no one actually cares about the efficiency of the market in the real world. In the real world, there are only buyers and sellers. Sure, a seller might want to sell something at a fair price because they have moral concerns or image related concerns, but that is still a seller responding to their own incentives. And sure, a buyer may want to tip more than is necessary or support a small business by paying a little extra, but this is a response to their own incentives, monetary, or otherwise. There is no actor in real life aiming towards an efficient market. This means that you, as the selling organization, and the market of buyers define the marketplace, and your pricing power is largely dependent on how well you frame your proprietary capabilities and value.
Buyers prefer perfectly open markets where everyone knows all the information available and where there is very little structure. Since there are always more buyers than sellers, this means that buyers can move from seller to seller at will and pit them against each other, driving prices down. Sellers, on the other hand, prefer auctions. These are perfectly structured settings where the seller can position themselves as a unique offering and allow bids and competition to obtain that offering to dictate the price.
Let’s think about the case of data sales. Data has to be sourced, tracked, aggregated, packaged, and executed. It can be sold at any of these stages, but the level to which it is commoditized vs. invaluable has a lot to do with what stage it is sold at. Let’s think about location data for a moment. Location data is simply data that indicates where a person is, or has been, based on GPS coordinates that are read by a user’s mobile device based on its communication with a satellite. An organization paid to create the technology and put that satellite in the air, and a company built the phone. Once they work together to originate that piece of data it is now a sourced piece of data. It is essentially worth nothing, but it exists. Now, a company comes along and scales an operation that can track this data across millions of devices, consistently over time. This data now has some value to it, but it is mostly commoditized, and limited in its usefulness. Now, a company comes along and decides to aggregate and organize the data. This means that they have aggregated groups of like data into forms that are ingestible for use so that companies can integrate it into their processes. The data is now useful, but still commoditized as access to GPS data is not uncommon, and the work required to aggregate and organize it is not proprietary. Now a company comes along and packages the data into usable groups and segments. There could potentially be some proprietary technology that goes into the packaging of the data, and the usefulness also improves significantly. However, there are no limitations on how many companies can do this so there is still some commoditization. Lastly, a company comes along and thinks about what other businesses will use this data for. They move from packaging to execution, and build platforms, and service models that integrate the packaged data into other workflows and execute on behalf of businesses. At this point, the product is likely very useful, and also potentially invaluable. By this, I don’t mean infinitely valuable, I mean hard to value precisely due to its uniqueness.
In the scenario above, a company that sells raw data that is simply sourced and tracked has very little pricing power. Of course, their costs may be very low, so the business may succeed, but since the barriers to entry are somewhat low, and there would be a number of other low cost competitors, the buyers will have a lot of control over how the market is structured and what the price is. However, a company that is executing for its customers has had to build their own proprietary software, systems, and integrations that allows them to do things like analyze the data and provide relevant insights, or measure locations in a way that tells businesses what their customers are doing or where they should build new stores, or target specific groups of customers with specific marketing messages. All of these executions make the offering more proprietary, and less commoditized. Of course, as technology makes it easier for competitors to build proprietary software, systems, and integrations like these, even the most unique offerings will start to slide down the scale towards commoditization. However, when the offering is unique and hard to value, the buyer has control over the structure of the market and the price to a much greater extent.
I just picked two relatively simple examples to explain the extremes. However, imagine a situation where you are a seller for DataMania, a fictional data company, which sells packaged data, and some executed insights. In this scenario, you may be perceived by some as a commodity because there is no proprietary effort that goes into packaging of data, but you also may be perceived as a unique offering by some who don’t have the ability to access insights in a cost effective way without your services. In this scenario, your aim is clear, you must accentuate the unique and premium nature of your insights, while at the same time accentuating the resource lift that would go into sourcing and packaging data that your customers can outsource to you.
I went through this somewhat drawn out example to illustrate how much is not set in stone when it comes to the structure of the sales process. Compared to the raw data seller, in this example, DataMania is a much more unique, and useful offering. However, compared to a company that sells executed end to end solutions, DataMania demands resources of the buying entity and is quite commoditized. The perception of the buyer is highly dependent on what other products and solutions they have used and been pitched before, and so much of their understanding of your offering will come down to whose frame is adopted as the starting point for the conversation.
If a client is concerned with the resource lift that they will have to exert in order to use your solutions, the way to frame the offering is against other solutions that are less useful and more commoditized because these solutions are not custom and usually take extensive dev work to implement. Sure, they will be cheaper initially, and you will be more expensive, but if the cost that your client has to endure in terms of resource commitment is a major concern to them then the comparison of the relatively small monetary cost that they will have to pay you can be framed to offset the major resource commitment cost of going with a cheaper competitor.
If, on the other hand, the client is concerned with duplication of resources you may have the opposite conversation. In this scenario, you come across a client who has already built internal systems designed to analyze data and spit out measurement reports and insights. If that client buys end-to-end fully executed solutions from your competitors, they will be paying for something that they already invested resources to build, and they will be potentially adding internal confusion by adding redundant systems. Positioning your relatively cost effective solution against the more expensive and redundant solution here makes sense.
The point is that client resource lift runs along a scale that is almost directly conversely related to price, and figuring out where your client wants to fall on those two scales relative to each other will help you frame the structure of the conversation and the positioning of your solution. All the while, the commoditization scale is overlaid on top of the conversation and the less commoditized your solution is perceived as being, the more you can charge for it and the more resource lift clients are willing to commit to have it.
You have the ability to frame your solution against any background and any other solutions that you choose to, and if you miss an opportunity to do this correctly, you can put yourself in a tough situation when it comes to aligning your offering with the clients priorities.
Dan Greenberg · January 8, 2026 · 5 min read
As sellers, we are trained from the onset to ask questions. Discovery is a core part of what we do, and as we develop our core set of skills, conceptually, we learn to ask better questions, and respond to the answers to those questions in more productive ways. However, we don’t do that in a vacuum, we only get better at asking and reacting because we learn more and understand more about the power of questions and how they contribute to a conversation, a relationship, and an entire sales process.
Think for a moment; why do we ask questions? Most of us will immediately move in our mind to an answer that is generally related to the idea of acquiring information, or learning from the client. This is important because it helps us know our client, and therefore sell to them in a more personalized and direct way. There is nothing wrong with this answer, it is 100% correct. However, if we inspect the client / seller relationship more closely, there are other reasons for questions that are not immediately evident, and they are very important because understanding the other reasons consciously will help us ask better and more productive questions.
There are actually three reasons to ask questions in a sales setting. As mentioned above, the first and most obvious of those reasons is to gather information, which we discussed above.
This is where it gets more nuanced and interesting. The second reason to ask questions is to prompt the buyer to think about their problems and to discuss their ideal outcomes. Notice that it is still an informational, and intellectual objective, the only difference is that the receiver of the information is not you, it is the buyer themselves. Buyers think about their problems and solutions so often that they can become mundane and part of their operational existence. It is important for buyers to spend time thinking about the real implications of their problems, and the real mechanics of potential solutions. If the buyer spends time building a solution, they become a collaborator with you and will be doing part of your sales work.
This is a really important concept to grasp because done correctly, what you are really doing is choosing teams, and in doing so putting yourself and the buyer on the same team, with the enemy being something of your choosing. Sometimes it can be an outside force, or it can be the status quo, or it can even be a competitor that has caused frustration, but this is a scenario you want to be careful with. The point is that the natural state of relationship between buyers and sellers is often adversarial, or at the very least, guarded and siloed. This is because buyers have been trained to think of sellers as people attempting to take their money. Asking questions that encourage your buyer to collaborate with you on the potential solution flips that script.
The last reason to ask questions is to release emotion. The more the buyer talks about their problems, and their desired outcomes, the more likely they are to get frustrated, angry, hopeful, or excited, and all are good. Apathetic buyers don’t make proactive decisions, which means they tend to stick to the status quo. Inspiring emotion inspires action in decision makers. If you can harness frustration or anger with the status quo, or harness excitement of hopefulness about a desired outcome, you have put yourself in a better situation.
There are other emotions that you can draw out in buyers through good questions as well. You can inspire curiosity in a buyer by asking a question about their industry that challenges them to think about why they are doing something in a certain way. You can inspire confidence in a buyer by asking a particularly intelligent question about their unique situation. You can even inspire calm in your client by asking a question that sets them at ease regarding their place amongst their peers.
I could go on, but the point is to think about the emotions that you will be eliciting in your clients through certain questions and employ empathy that will allow you to understand what that person is looking for, and try to navigate in that direction.
What is the common thread in all of the emotion and conversational strategy above? It is that it mirrors basic human social behavior. Good conversationalists ask good questions and inspire emotions in their counterparts that move the relationship forward. We all have a lot of practice in basic human social interactions, and no matter if we realize it or not, our aim is actually to allow those we are interacting with to release negative emotions and help to replace them with positive ones. Think about every non-frivolous conversation you have ever had. One side starts with an issue, the two people talk through it, and hopefully the person with the issue feels a bit better having talked through it. That is a simple and repeatable roadmap for client interactions because client interactions are social interactions.
So often in our sales interactions we forget this basic behavioral rule. We focus on the business side of the interaction and forget that there is a social component that is just as, if not more, important.
Dan Greenberg · December 18, 2025 · 8 min read
Sam Altman and his associates reportedly have a betting pool about when there will be a $1Billion company staffed by a single person. The premise, of course, is that AI agents can carry out all of the other functions that companies would ordinarily need, so the company itself can be run by a singular human being who has created or purchased custom agents to do all of the other functions.
Sam Altman is a genius and far be it for me to argue with him but on this point he is wrong, and here is why.
Sam (Yes, I’m on a first name basis with him even though he does not know who I am) is looking at companies in terms of how we define and understand a company today. However, as soon as the development of AI tools allows people and companies to automate today’s functions and turn their focus to new functions, ideas, and ways to service customers, people will optimize themselves and companies will look very different than they do today.
Let’s look at this another way. Human Resources does not have a long history, they did not used to exist. But, over time companies started to make more money, and people began to find new ways to exploit companies. Companies became more efficient through automation and technology, and therefore more protective of their money, property, and status quo. They also had more money around because of said efficiency and built HR teams to protect themselves legally. Of course, HR teams have evolved to do more than that, but the basic function of an HR team is to protect a company, legally; and the need for that functionality only exists because it can exist. In other words, greater efficiency has led to the ability to add functions that are now necessities, but would have been seen as luxuries in the past.
It is similar to Parkinson’s Law which states “Work expands so as to fill the time available for its completion”. This is a quote from a 1955 essay by historian C. Northcote Parkinson. Parkinson also observed this on the dimension we are discussing, people and functions. He talked about the idea that the number of workers within public administration, bureaucracy or officialdom tends to grow, regardless of the amount of work to be done. This he attributed mainly to two factors: that officials want subordinates, not rivals, and that officials make work for each other. As our corporate environments continue to look and feel more bureaucratic we can clearly see the crossover between the public domain discussed by Parkinson, and the private corporate domain.
I gave the example of human resources above, but let’s also look at customer success teams. The customer success function, like HR, did not exist in the not too distant past. There was product, sales and administration, and sellers dealt with clients, so there was no need for a dedicated client success or service function, specifically in the B2B world. Over time, as markets became more congested and fragmented, and switching costs decreased, it became easier for clients to churn, so it made more sense for companies to start hiring more people and spending money to keep clients around. As the technology fueled competition, and made room for more slices of the pie to be cut, it also grew the size of the overall pie, and therefore freed up money for businesses to focus more on interpersonal interaction and relationships. In other words, more technology made it so that companies could find a competitive advantage in spending more time on the non-technical pieces of their business in order to differentiate.
We can argue about whether this is good or bad for business, or for clients, or for the economy, but the point is that historically, step function leaps in technology have not led to smaller workforces, they have led to larger workforces once the market has adjusted and companies have figured out what to compete on. Sure, Sam may be technically correct as in the transition period, there may be companies who find efficiencies before the overall market adjusts, but the point is that in economic equilibrium, or anything close to it, companies will find something to compete on, or something to leverage for efficiency, and will therefore not want to cut resources, because it will be more efficient and profitable to add resources to improve their abilities in these areas, and that will include adding people.
Let’s look at another historical example for fun: Electronic spreadsheets vastly diminished the amount of time that an accountant needed to spend building reports. Could you imagine writing numbers into graph paper every time you needed to build a revenue model? However, the advent of Excel and Google Sheets did not lead to smaller accounting teams, it led to more historical modeling, and the need for higher levels of certainty and greater reporting detail which has led to larger accounting and finance teams, and the proliferation of forward looking modeling and financial analysis. Reporting that was unimaginable 40 years ago has become table stakes for any business.
I get it, Sam might say, but AI is different because it can do anything that humans optimize themselves to be able to do. In other words, we no longer need an accountant to run that report, because an AI agent can do it. So we are in a fundamentally different place in terms of technology development.
He has a point, but let’s clarify. As it stands now, we don’t have Artificial General Intelligence (AGI) and we won’t have it until mid century, at the earliest, that is the prediction. AGI will conceptually be able to ingest wide arrays of inputs and act with human levels of expertise across many areas of function as opposed to what we have now which is limited by task and breadth of function.
But even as we develop AGI, assuming it plays out as we expect it to, AI already is, and will always be better than humans at many things and not as good as humans at other things. The best companies will know how to leverage comparative advantage. AI models will have to compete with other AI models and there is a significant cost to customize and host, so humans are likely to retain a comparative advantage in the areas where we are more efficient, like human interactions, judgement, and planning. Think about it, as AI models continue to improve, and are forced to compete against each other, we will need humans to build those ever improving models, so at a certain point, it will make more sense to find the jobs that humans do best and and focus the AI on the things it does best rather than continually iterating on new AI models for each and every function. This is what mature markets will bring to AI development, when we get there.
We can also look at this from a very human perspective. Fads tend to change over time to reflect what is hard to acquire. We see this with the retro bespoke style movement. We can also see this, interestingly, through sociological studies on skin color treatments. In most northern European and North American countries, historically, tanning and skin darkening has been a sign of beauty, while in tropical countries it has been much more likely to be the case that skin lightening treatments have been signs of beauty. Simply put, things that are harder to come by are seen as valuable for the very reason that they are harder to come by.
So, it is very likely that over time, as it becomes increasingly easier to execute on functions and outputs that differentiate businesses today, it will end up being the things that businesses cannot do today, that new technology will eventually allow them to do, that will be competed on most fiercely. Those new functions and outputs will be harder to execute on, and therefore more valuable to customers. Those new functions and outputs will be at the cutting edge of technology, and therefore necessarily need human input and humans to work alongside the technology. And because those new functions and outputs will be harder to compete on, businesses will look for ways to gain an advantage, which will often mean hiring more people to perform in very different looking roles, but nonetheless, hiring people.
This will mean that in the not-to-distant future all of the functions that we currently understand that need to be accounted for in a company may be able to be executed on by one person and a cadre of AI agents. However, the new frontier in business will be the functions and outputs that differentiate one business from another in customer service, in efficiency, and in product-to-market capabilities. These things will always exist at the vanguard of technological improvement, therefore always necessitating some level of human involvement and teamwork between humans and technology.
Dan Greenberg · December 3, 2025 · 7 min read
Revenue is increasing! Pipeline is improving! Sales cycles are getting shorter! Those are all good things, but scaling a sales organization eventually means maturing the organization to the point where revenue is balanced with cost, and the biggest cost in any organization is people.
It is not the case that margins have to be positive at every point in the business growth cycle, and it is not even the case that margins have to be improving at every point in the growth cycle. However, scaling a revenue organization in a world where the only way to increase revenue is by adding headcount is not a viable path.
As I wrote about in more detail a couple of weeks ago, in my November 20th post, Sales Always Get Incrementally Harder. This means that it will consistently cost more money to make a sale as your business grows, and this means that if your organization is only able to scale revenue by scaling headcount, eventually your margins will go belly up and your scaling engine will break.
Salespeople are humans, and humans will always do their best to optimize their output given their incentives. This means that sellers will spend their time trying to close the easiest deals. By definition, this means that every incremental sale will get harder than the one before it. The other important piece to grapple with, especially for earlier stage companies, is that founder led sales tend to run into scale issues. Founders are well connected and can employ significant amounts of company resources to close deals. Plus, when they sell early in the lifecycle of a company, they tend to be selling to those who are already bought in; the early adopters. They can have business leader to business leader conversations with people who already understand what they are doing and are already interested. In other words, they tend to close the easiest deals. When founders then try to build scalable sales teams, the sellers don’t have the cache that goes along with being the CEO, they can’t marshal the same resources, and they aren’t talking to early adopters who are halfway bought in. Lastly, as a business grows, it has to hire more people and build operational models to suit more people. Both of these things are harder to do at scale, and therefore cost more. So, all of that is what causes increased difficulty, and therefore, increased cost for each incremental sale.
Once we understand that incremental sales get harder, we can begin to wrap our minds around the concept that as costs increase, the margins decrease and that will mean that the only way to fundamentally improve margins over the long run is to set up process and operational systems that allow for fewer people, and fewer highly paid people to drive more business and work with more accounts.
This is why it is important for revenue leaders to focus on revenue per head even in early stages of growth where it may be advantageous to spend a bit more and sacrifice margin to achieve market share. None of this is to say that decisions like overspending and over-hiring in order to race to market are always the wrong decision. The point is that increases in revenue, no matter how rapid, do not signal the maturity of a revenue organization. Achieving revenue growth is the first step, but the second, and much less flashy step, is achieving balance when it comes to cost per revenue.
Achieving balance in cost per revenue means understanding how much the incremental cost per sale will increase over time, and building a set of processes and support that serve to offset those increases in cost so that when more people are hired, and revenue increases, margins remain relatively unaffected. This is a lot harder said than done.
Of course, we now live in the world of AI, and there are a number of AI tools that can be used to streamline efficiency, but only if they are used in the right way and built into systems of working and operational models that already make sense. The proper operating model for each team or organization looks different, but there are a few principals that are true across the board.
Fundamentally, it is important to wrap your mind around the idea that increased revenue and other metrics around sales and pipeline growth are good. However, without the appropriate strategy and methodology; without the proper systems and processes; without the the right training programs and tools, growth and margins will tend to travel in opposite directions. In order to work towards balancing the two, an organization that is trying to mature itself must set its goals in terms of revenue per head. It must build systems that orient the organization towards operational improvements, and most importantly, it must take actions that make it easier for people do their jobs instead of focusing on actions that simply drive more revenue.
Dan Greenberg · November 20, 2025 · 10 min read
How many revenue organizations have you come across that operate on the premise that each additional seller that gets added to the team will generate X amount of revenue based on current seller metrics? The answer is “almost all of them”.
This is a form of focusing on revenue per head, but it is a short sighted, and ultimately self defeating version of it. The assumption that scalability will remain constant is the biggest issue with the premise, and the result of building a revenue organization on this premise is almost always missed goals, overspending, and the eventual need to execute layoffs and other cuts.
I took a job at a technology company a number of years ago. They, and every other company, were coming out of a rough patch in the broader economy and believed that they were in a good position to scale the business. When they started to set goals and hire with their renewed growth mindset they had 270 employees. I was hired in November, and their goal over the course of the following calendar year was to hire about 130 people including 70 sales people which would put their total headcount at about 400 and would bring the number of salespeople up to 120. In other words, they wanted to increase headcount by almost 50%. For some context, I was hired to run a very specific business unit which was meant to include a product person, about 6–7 sales people and another 5–8 support people.
The thinking was simple. They had a specific trajectory in mind based on their current sales team and figured that each additional seller could sell about the same amount as a current seller so they built their cost structure and hiring plan based off of revenue projections that matched those of the current sales team. By mid summer it was evident that things were not going according to plan. The revenue projections were falling short, and not by a small amount. By late fall the missed projections had to be reckoned with. Although hiring had not kept up with goals and the overall employee count only reached about 360 with the sales team growing too close to 100, it was still necessary to enact significant layoffs across the company, and mostly in sales.
When the dust settled, employee count returned to about 280, just above the numbers it had started at, and the sales organization returned to its prior size. In one way you could look at this and say, “well, they tried, and when it was all said and done, they ended up where they started so it could have been worse”. But this outlook is far from descriptive of the situation. In all of the turmoil, they lost good sellers they would have wanted to keep, who left because they had a bad taste in their mouth and because people they liked to work with were laid off. They had hired quickly and ended up with some employees that were not vetted using the same standards as in the past in order to meet hiring goals; these were employees that they would not have ordinarily kept but were needed in order to keep teams at a certain size to operate the business. They hired people out of good jobs and then left them unemployed. They spent a lot of money ramping up operations only to ramp those operations back down almost immediately. All in all, the business lost significant time, money, and reputability, not to mention the effects on the laid off employees.
All of what I described above seems intuitive and understandable, but yet, we see so many companies go down this and similar paths. So, what causes this type of strategy to be employed, and what is the alternative?
What causes this type of strategy to be employed is a reliance on historical data as a predictor of future results. Many of us have seen the disclaimers on financial products like ETFs that say something like “historical performance is not a predictor of future results”. We understand this intuitively, but we crave data to support our decisions, and in the absence of a true understanding of how a revenue team scales, we rely on that data without factoring in other pieces of information.
Specifically, it is important to understand that salespeople are humans, and humans will always do their best to optimize their situation under their current incentive structure. This means that sellers will spend their time working with the easiest clients to sell to. By definition, this means that every single incremental sale is harder than the one before it. Of course, in the real world, it doesn’t always work out exactly like that, but the guidance generally falls in line. If one client is easier to sell to than another and I make a deal with that client, I am then left with the client who was harder to sell to.
If your team has 400 accounts and 10 sales people, each sales person will have 40 accounts and they will work on the 20 easiest to close. If you increase to 20 salespeople, each salesperson will now have 20 accounts, and on average, they will each only have 10 accounts that are considered ‘easy to close’. Of course, more people will lead to more sales than before but not anywhere close to 2 times the sales. But guess what does get multiplied by 2? The cost of hiring all those people.
The other fatal flaw has to do with the business cycle and reversion to the mean. Most of the time when executives make the decision to hire a lot, it is when things have started to go well. They look at the trajectory, the growth in ARR, or pipeline, and think to themselves, if I have 10 sellers doing this, imagine if I had 20. When the cycle is down and things aren’t going well, the same desire is not there. But all businesses go through cycles and after a period of growth that is unexpected, the next phase is statistically likely to be a reversion to the mean. This does not mean that things will go poorly, or sales will drop to zero, but it does mean that unexpected growth is usually not sustained at the high levels that causes the optimism, which means that the business won’t be able to support an influx of new sellers when the current cycle ends.
The other really important piece to understand, especially for earlier stage companies is that founder led sales tend to run into scale issues. Founders know a lot of people and can marshal the resources of the company. Plus, when they sell early in the lifecycle of a company, they tend to be selling to those who are bought in; the early adopters. They can have CEO to CEO conversations with people who get the concept of what they are doing and are interested. In other words, they tend to sell to lower hanging fruit. When founders try to build scalable sales teams, the sellers don’t have the cache that goes along with being the CEO, they can’t marshal the same resources, and they aren’t talking to early adopters who are halfway bought in.
So, all of the above is what causes increased difficulty for each incremental sale, and the lack of understanding of these principals cause business leaders to lean too heavily on historical data and over-index on optimism. So, what is the alternative to this type of approach?
Certainly we could just be extremely conservative with our projections and give our new reps time to build up their book of business, and there is some merit to that approach. But there is something much more powerful that can be leveraged as we start to scale a business. That approach revolves around understanding the lowest cost of the next incremental dollar and matching up the right resources to drive that next dollar.
We have already established that each incremental sale gets harder, which is another way of saying that it costs more to close. We have also stated that revenue per head is the most important metric. So, how do we marry the two? Well, we have sellers who have built a book of business and have repeating revenue that they are managing. In many cases, the easiest incremental dollar comes from our existing clients because they have already demonstrated that they understand the value proposition. The problem is that we are paying our sellers for managing the business and not for growing it. We need to understand the relative difficulty of growing business compared to driving new business and set up incentive structures such that our sellers self-select into the most ideal function for driving growth.
Oftentimes book management becomes lucrative enough that long time sellers can sit on a patch of accounts and be assured of making money by simply managing their existing business which means that any potential new business in their patch does not get worked. They are essentially crowding out new sellers and exacerbating the problems around increased difficulty of each incremental sale. I am not advocating for setting new business goals, because that assumes that we can accurately predict exactly where our sellers should be spending time, going into the year. I am, however, advocating for setting overall revenue goals for sellers such that they are incentivized to push for growth, either with their existing book, or with new business. Once your sellers tell you where they want to go, you are now able to either have client success play a bigger role in managing existing business, while your sellers focus on new business, or you are able to distribute new business to hungry sellers while your more tenured sellers focus on growing existing accounts.
The basic idea is that if your tenured sellers can get paid 80% of their goal through book management and order taking, you end up not incentivizing growth. But much worse, you allow those sellers to keep accounts that they won’t put effort into. This will mean that your new sellers are left with accounts that are not likely to buy and are therefore not set up for success.
I don’t mean to imply that setting up these incentive structures is easy. However, the key point in all of this is that new sellers have a harder job than tenured sellers, and we need to expect that productivity will decrease as we scale, simply because every incremental sale gets harder and more costly. We can combat the issue by taking into account this reality and working to build high value territories for new sellers with realistic targets, all while incentivizing more tenured sellers to focus on the clients where growth potential is greatest.
Dan Greenberg · November 5, 2025 · 8 min read
Organizational and business leaders are struggling with how to build for the future. This makes sense because we live in a world where the promise of AI is very real and apparent, but the current output is less reliable and transcendent than the promise. In this article, I am going to focus on revenue organizations, but this logic can be applied across functions.
Business leaders across industries are embracing AI, partially because they want to and partially because they have to. Imagine being a CEO and telling your board that you aren’t leveraging AI tools; that is an expensive ticket to the land of severance and headhunter phone calls. So, the correct answer for any business leader is, “Yes, we are leveraging AI tools and looking toward a future where we can build more automated workflows, and achieve more efficiency through AI usage”. This is a great answer, the only problem with it is that it inevitably leads to the next logical question from the board, the boss, or any other investor. And that question is, “How is it affecting the bottom line?”
The only real way for AI usage to affect the bottom line is when tools replace humans. The relatively lower cost of tools replaces human employees bringing costs down without affecting revenue, and, Voilá! Improved bottom line.
The only slight hitch with the picture painted above is that it doesn’t work yet. Certainly, there are functional business areas and specific workflows that can be automated with AI tools. We can see that across businesses, and it is evident from large recent layoffs at companies like Amazon and the like. However, at scale, the outputs generated by AI tools cannot replace the work humans do, not yet anyway. So, what we see is a lot of stagnation. This is evident in the economic numbers, and the reason it is happening is that business leaders still need people but they already told their investors that the AI is doing the work. So, they can’t get rid of most people, but they also can’t hire. Stagnation.
Looking at it through a technological lens, what we are saying is that the promise of AI has not yet been met by the operational usability of AI tools for most functional business areas. This mismatch between the technology and the outputs exists for two reasons. The first reason is that the technology is so new that companies are building tools quickly and getting them in market but the market is not mature enough yet to create a cohesive product feedback loop so we are left with exciting capabilities and wanting usability. This issue is somewhat transitory and will improve over time.
The second reason is more enduring. AI tends toward generic outputs. Large Language Models, the foundation for most AI outputs, work off of numerical representations of data, called vectors. They look for the most common possible output and serve that up to the user. This means that AI tends toward generic outputs. Most of the time they are right, and often they are very helpful, save us much time, and allow us to get much more done. However, they are generic, and that means that they still need a thinking human to apply them to the specific situation that is being solved for. This is especially true in revenue organizations when dealing with prospects and clients where it is not just about the right answer but it is about resonating with someone who is reluctant to commit time to listen to what you have to say. I am not saying anything radical here, but the result of all of this is that we cannot yet rely on AI, and we cannot yet pass off entire tasks to AI across the majority of business functions. AI is still a tool to be used by humans, not a replacement.
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We see this across industries, but I’ll give one example. The media industry has been using algorithmic models to match up ads with media inventory to serve them to people for 25 years. The industry now mostly uses AI tools. The tools themselves are incredible feats of technology but the improvements are modest because the algorithms were already good, and because the output from the AI tools can’t be leveraged by humans in a complimentary way that allows for revolutionary technology to translate to revolutionary results.
The technology and the promise of AI are a revolutionary improvement on what we have had in the past. However, The output and results of AI tools are only incrementally better than what we have had in the past.
There is a fundamental barrier preventing revolutionary results and that is the lack of compatibility between AI and the human ability to leverage that output. In other words, the AI knows the perfect answer but it is not possible to express in a way that humans can understand it and use it because it can only be expressed with a massive amount of data. At the same time, that perfect answer is generic and lacks nuance. This means that in order for the AI to be usable by a human, the output must be simplified into something that is less accurate, and in order for it to be highly useful, it needs to be augmented by human nuance. Until AI bots can act effectively on the analysis done by AI, we need to contend with the issue of compatibility between the AI tools doing the analysis and the humans taking the action.
If you inspect the conclusions drawn above you will see that the outputs from AI are much more powerful and the promise is even more so, but it is not revolutionary, and therefore, not a black box. We have seen these types of incremental output improvements before and we have a sense of what to do with them. So, let’s return to the original problem posed above which is how do you build an organizational structure for ‘now’ that supports the use of AI tools and is prepared for future advancements in AI technology and outputs. The answer is that AI tools finally give us the ability to flatten our organizations and empower our top performers, something we have been wanting to do for some time but have not been able to do effectively.
Ill be spending more time on organizational structure and process in a future article, but here is the cliffs notes version. The traditional structure of an organization is pyramid shaped. It is this way because we need centralized direction and process to flow down through the levels so that multiple people operate using the same procedures. This is necessary in order to attain scale and measure success. However, because AI tools can replace human research, data manipulation, and data analysis, and because these tools can help us personalize, we now have the ability to transfer those functions to our tools. Much more importantly, we have the ability to decentralize and localize process based on the needs of individual books of business. High performing sellers can work with tools to make localized decisions on how to allocate time and resources and how to address their individual book of business. High performing marketers can work with tools to make localized decisions on how to construct and distribute content and make decisions on where to target time and resources from a cohort perspective. We certainly still need some layer of leadership because strategy and direction must be made at levels above process decisions, but we don’t need as many layers as we have had, and we can distribute that decision making power to our top performers.
All that may seem logical but here is the key to making it work. We spent significant time above discussing the incompatibility of humans and AI tools in the present, so we still need a function that sits in the middle of the high performing person and the AI tool. Your high performing sellers, marketers and relationship builders are not the people who are going to learn to use and interact with the AI tools. And even if there are some that will, that is not where the organizations want their high performers spending their time. The connecting function has to be human, and it has to be a person that will translate the massive amount of data from the tools into the important pieces for the high performers so that they can add the human touch and nuance of an expert. That person also has to input messy real world data into the AI tools in an efficient and accurate way. In other words, we need a new kind of expert. We need an expert who can smooth over all of the problems generated by the incompatibility of our human brains and the AI tools. When we have that in place, we can create a working functional pod that includes the right tools, the high performer who understands the market and the human interactions, and the expert who can liaise between the two.
The idea is that we are not solving for how to use AI tools. We are solving for how to make current outputs more compatible with human uses. Once we orient the problem in that way it becomes a lot easier to see how to harness AI now, and into the future.
Dan Greenberg · October 22, 2025 · 6 min read
Sales presentations are like art in one very informative way. People have to be excited by them, emotionally. If your client is not interested in, and excited by your presentation, you will have lost the opportunity to be influential in that setting. Your buyer may learn a bit and take information back to the team, but the eventual decision will be made based on a myriad of outside influences, and none will be your presentation. If the client is emotionally interested in your presentation, then, and only then, will they start to look for intellectual justification for their excitement.
The same is true for art in the sense that if a potential buyer of art is not emotionally interested in a piece, they will not evaluate its worthiness for purchase.
All of the above is relevant because it means that when we are creating presentations and planning for their execution, we need to think about emotional connection and excitement rather than imparting information and expertise. Building presentations in this way is, in and of itself, an art form, and what comes out on the other side should be considered to be a work of art.
Bad sellers sell products, and good sellers sell solutions; but the best sellers sell outcomes and value. The question is, how do you illustrate an outcome or the value of something? It is abstract. A product is easily perceivable, and a solution is understandable. But, an outcome changes the state of being for the client and is therefore not perceivable given their understanding of their current situation.
Because of this, sales is one of the most creative of all professions. The only way to illustrate an outcome is through telling a story. Illustrate everything. Whether it is whiteboarding, videos, graphics, visual slides, or illustration through storytelling, we should not be talking to people, we should be showing them a new reality and helping them grasp it and understand it.
We should be telling a story in which the client is the protagonist. The story is one in which they can eventually achieve an outcome that is a fundamental shift in relation to their current reality. For that reason it has to be explained via a story where the beginning is the status quo, which has to be shown to be an issue that must be overcome. If a seller cannot show the need for a new reality which would lead to a new set of outcomes, then no matter how well the solutions are explained, it won’t matter because the need for a new reality is the only thing that would make the buyer feel a need for solutions to get them there.
One of the things that made Steve Jobs so incredibly effective as a presenter of information was the simplicity and illustrative nature of the slides he used. You rarely saw words on his slides, almost never saw sentences, and never saw pros or bullet points. In Carmine Gallo’s book, “The Presentation Secrets of Steve Jobs” he notes that, “New research into cognitive functioning — how the brain works — proves that bullet points are the least effective way to deliver important information. Neuroscientists are finding that what passes as a typical presentation is usually the worst way to engage your audience.” In other words, what most people put on slides does not work. It is not engaging and it does not paint a picture or tell a story that will show the client what a reality that they are currently not existing in could feel like.
Sales presentations really can be like art. Sure, it’s nerdy, somewhat boring, and definitely not culturally relevant art, but art, nonetheless. Buyers have to be emotionally engaged in the story, and then will find intellectual justification for their excitement and decisions. Jobs’ presentations explained the status quo with his voice as the narrative and his slides as the illustrations, in a similar way to how you would think about telling a story to a small child. He allowed the slides to simply illustrate and his words to complete a narrative from start to finish. He would explain and introduce, and then animate the problem, which was the status quo, as well as those trying to imprison the buyer in that status quo. Then he would talk about the vision of a future desired outcome, and what a different reality could look like for the currently imprisoned buyer. And then, he would resolve the matter by reassuring that buyer that the outcome is simple to conceive, and does not require heavy lifting on their part. Sounds a lot like the progression of a simple story. It starts with a problem which rises in tension and climaxes. We understand the outcome we want to get to and eventually the problem is solved and we see what the resolution looks like.
I’ll leave you with one other quote from Gallo’s book on Jobs’ presentation style, because it does a good job of illustrating the starting point and ending point of the story that every presenter is trying to tell. It comes directly from his interview with Jobs himself. Jobs says, “A leader carries a vivid image in his or her head of what a future could be. Leaders are fascinated by the future. You are a leader if, and only if, you are restless for change, impatient for progress, and deeply dissatisfied with the status quo.” He continues to explain, “As a leader, you are never satisfied with the present, because in your head you can see a better future, and the friction between ‘what is’ and ‘what could be’ burns you, stirs you up, propels you forward. This is leadership.”
It is the job of a presenter, of you, as a seller, to bring the buyer along, and instill that same sense of dissatisfaction with the status quo so that you can show them what that future can look like.
Dan Greenberg · October 6, 2025 · 8 min read
Demos or product demonstrations are a subset of presentations with a very specific goal. They introduce a challenge for sellers, because they are often asked for by the buyer. This means two things. The first is that by asking for the demo and getting it, the buyer, either consciously or subconsciously, is in control of the situation. The second is that a demo allows the buyer to evaluate a solution and compare it to those of other vendors on their own terms. The buyer gets to be the judge, and the frame is around what problems the solution has, and how it could be better. The frame we, as sellers prefer, is one that focuses on the buyer’s problems and the need for a solution to change the current status quo.
This means that as sellers, we want to be talking about problems and desired outcomes, and skip over the conversation about solutions. When we are talking about problems and outcomes, we are in control, when we are talking about solutions, the judge of the solution, or the buyer is in control. A demo, on the other hand, is axiomatically about solutions. Sometimes the client pushes a seller towards giving a demo, and sometimes it just makes sense to do one as you progress towards the latter stages of a sales cycle, but regardless, it is important to know how to run a demo in order to avoid the framing problem mentioned above. If you find yourself subservient and your solution being judged you may have a perfectly cordial interaction with the buyer, but you will lose the ability to influence the decision.
One thing to think about before we jump into the meat of the conversation is that whenever possible, it should be a solutions engineer, or account manager, or sales specialist who runs the demo. Basically it should be anyone the seller trusts, but not the seller. The two high level problems with the seller talking about solutions are that it puts the buyer in product judgment mode, which we discussed above, and it exposes the presenter as biased, and focused on the sale when the seller should remain positioned as a consultant whenever possible. Having another person run a demo at least helps to alleviate the latter problem, and it leaves the seller more readily able to combat the former. This can actually be accomplished by pointing out slight flaws in the solution that the demo giver did not point out. These flaws should be in areas that are of less concern to the buyer when possible. This increases trust in the seller, but also serves to highlight the positives of the solution as they are contrasted with the slight negatives.
Regardless of who ends up doing the demo, whether it be the seller or another person with the seller there to add color, there are a few things to think about.
Frame: Frames are very important. It is essential to frame the solution by talking about the problem first. A frame can also be set by positioning the solution against something that is qualitatively different. If there are a few options that the buyer can decide between that have qualitative similarities, those options can be bundled and labeled as the set of solutions that would be helpful to them. But the qualitative difference between your solutions and that bundle can be labeled as what can really get them to the desired outcome.
Illustrate: The solution should be framed as something that can be really great and exciting, but there is a nuance here; it is actually the solution that leads to the desired outcome that can get the client to that really great state, not the solution itself. In other words, avoid the trap of talking about features and products; every set of solutions solves a problem and is framed by the outcome it drives, not the solution itself.
Balance: When you position your product as being great but you mention a small detraction or issue it actually has the effect of letting the buyer feel as if their job has been done for them. When we talk about the buyer framing themself as the all-knowing judge, and looking for problems with any solution, if they feel that their job has been done for them, they are less likely to aggressively look for issues to bring up.
Label: I alluded to labels above, but they are very important. Label your sales engineer as an expert, label your solution as transformational for their business, label a specific feature as the lynchpin that allows for a true qualitative difference. Labels are important if they are defensible and relevant because they will stick in the buyer’s head and become their way of thinking about your presentation.
It is also important to make sure to ask questions throughout demos and as you are finishing your demo. Ask the client if they can envision themselves and their team using the solutions, this will help drive visualization. Ask the client if the workflow you are showing helps them understand how to combat the problem they are having. Ask them if there are any other issues that are making the day-to-day tougher for the individuals using the tools. All of these questions help the demo giver relate directly to the client in real time.
More importantly, remember that the demo is a story like any other story. It starts with an intro, and then moves to a framing of the problem. After that, it focuses on the solution. But, it does not focus on the solution as a list of features, rather, it focuses on the solution as a story about how each individual using the tool will be made more efficient from the start of the business process that the solution drives through the end of it, and then how that efficiency reflects on the overall business. The demo giver, or the seller aiding the demo giver, has to be consistently orienting the client as to where in the workflow they are, they have to be constantly stepping back and explaining the whole workflow, and how each part fits in, and they need to be constantly asking questions, and then asking the client to visualize the workflow as a whole and think about how it would improve efficiency.
Regardless of the type of presentation you are giving, it is imperative to have a plan. There is a well known quote from President Dwight D. Eisenhower that I love, and it fits the situation well.
“No battle was ever won according to plan, but no battle was ever won without one.”
–Dwight D. Eisenhower
Having a plan is not important because you will have the opportunity to stick to it the entire time. Rather, having a plan is important because it is a baseline to fall back on when your meeting gets derailed. It acts as your north star. It is much easier to reform, or iterate on something that already exists than to try to develop something from scratch on the spot.
This means that in addition to your story, and your materials, you should develop a plan for any meeting, demo, or presentation that is completely separate from your story and your slides. The plan should include the following:
Your plan should also include thoughts on how you plan to build rapport with the individuals on the buying team, how you plan to discuss ongoing partnership and support setup, and how you plan to address any outstanding issues or support concerns brought up in previous meetings.
If you plan well, and prepare to focus on the core competencies of successful demonstrations, you may not always gain buy-in right away, but you will be likely to avoid many of the traps that see sellers and their solutions relegated to the pile, or treated like the offers of just one of a number of vendors out there. Executing on the skills above will give you the opportunity to remain relevant and influential with the buyer.
Dan Greenberg · September 17, 2025 · 8 min read
As sales leaders, we talk about it all the time. The best way to influence buyers is through telling stories. The idea is to create a beginning, middle, and end, where the buyer is the protagonist and your seller is a consultative supporter along the way. The only problem is, we don’t really do much as organizations to help prepare sellers to act on this type of sales methodology.
Think about it; when we train sellers, we train them on products and features, when we ask sellers about their pipeline, we want to know how quickly deals are moving and when they will get to the next checkpoint, and when we talk about goals and numbers, all we want to know is what is closing and when. None of this helps sellers, or incentivizes them to stop and develop consultative story based approaches for their sales engagements and relationship building.
So, the question is; how do you get your team to tell stories instead of hawking products? How do you get your team to think about the buyer’s buying journey instead of only focusing on the selling checkpoints? How do you get your team to focus on the long term cultivation of good potential clients instead of racing towards short term deals that may not even be more likely to close?
The reason that sales is about storytelling is because people make big decisions based on emotion and then justify those decisions with intellect. So, in order to be influential we must tap into that emotion, and the only way to do that is through storytelling. People do not listen to facts, and data and get moved emotionally. Stories move people emotionally. The facts and data need to be there so that the buyer feels that risk is alleviated, and can feel comfortable in explaining their rationale for the decision, but the actual decision is made based on the emotion and not the facts.
Even the description I just gave about the use of data and facts to justify decisions helps prove the point. The data and facts are used by the decision maker to alleviate the isolation and fear inherent in being the person responsible for the decision. The decision maker is using the data and facts to solve an emotional problem; fear.
Take some time to think about the last number of client pitches that you have sat in on or been a part of preparing. We all fall into the familiar pattern; the rut, of showing products on slides. We tell the client about their problem, and then we explain how the solutions will fix the problem. But that leads to two big problems. First, the buyer is not the protagonist, the solutions are, and second, there is no story; no beginning, middle, and end. It is a stagnant picture of now, and a stagnant picture of a potential solve, but talked about out of context with no vision of the outcome it is driving. We consistently use similar presentation tactics and formats, and then we wonder why there is no material improvement in our teams’ ability to close deals over time.
Sometimes the issue is that the seller does not know how to tell a story, and sometimes the issue is that the seller does not know what story to tell, but let‘s talk through those issues and how to solve them for your teams.
I have mentioned this breakdown in past articles, but it is a good framework for talking about storytelling in this context. Bad sellers sell products; good sellers sell solutions; great sellers sell outcomes, and the best sellers sell value. The traditional slide presentation talks about problems and then matches them up with solutions. For the purposes of this conversation, let’s talk about how to get from solutions to outcomes.
How do you illustrate an outcome? It is abstract. A product is easily perceivable, a solution is understandable because it presumably links back to and solves a problem. An outcome is harder to understand because humans don’t always have the ability to perceive a state of being that is not the one they currently exist in. A conversation about outcomes changes helps them to envision a new state of being that they have a part in bringing into existence. It helps them visualize something that is not currently perceivable. In order to do this we have to encourage our sellers to be creative and dynamic and to spend time conversing with clients outside of the construct of solution slides that match up to problem assessments.
Sales is the most creative of professions because the only way to illustrate an outcome is through telling a story. Sellers should be encouraged to whiteboard and ad lib conversations and concepts in every sales interaction because talking about slides is not communicating. It is simply showing a buyer a solution that they could have researched on their own. Instead, sellers should be telling a story in which the buyer is the protagonist and they can eventually achieve an outcome that is a fundamental shift in relation to the current reality. For that reason it has to be a story where the beginning is the current reality. The current reality has to be proven to be an issue that must be overcome. If a seller cannot sell the need for a new reality or a new set of outcomes, then the seller will never be able to sell any specific solution or set of solutions.
This is where discovery and insights come in. The seller must understand which story they are going to tell, and only by understanding the most vivid and pressing issues, can a seller understand where to start the story and how to progress it. Asking the right questions, and earning the right to ask those questions by providing insights that are not related to specific products and solutions will help the seller understand exactly what story to tell.
Once the seller knows what story they want to tell, it has to be constructed. There are a number of ways to go about building a good story. I have opted for one specific model most often, but there are plenty of other good ways to do it.
I have previously written about the four components of a sales story, but I would like to do so today in the context of the continuity of the story itself. I would also like to do so in the context of training sellers to use this methodology.
The first section is the intro and the hook. In this section your sellers explain who they are and why they deserve to be in the room; this is not about the company or the solutions, but about them personally. The goal is to establish the client’s belief in their right to be there and be part of the conversation.
The second section is the problem section. The goal of the problem section is to ascertain agreement from the buyer on the fact that there is a problem, learn how the client describes, characterizes and values the problem, and gain buy-in from the client on the reality of the issues being caused by the status quo. That is to say; your seller should be kicking off the story by painting a picture of the current reality and all of the human problems that are caused by it.
The third section is the outcome section. The outcome section is meant to understand the client’s expectation and desired outcome, and the goal of the section is to allow the client to paint that picture, and to introduce the idea that there is a singular solution that can bridge the gap from problem to desired outcome. Notice that in this part of the story, your seller should be allowing the client to participate in the creation of the story on the fly, and they should be showing a linear progression, not from problem to solution, but from current reality to new reality, that is being driven by the buyer and the buyer’s team.
The fourth, and final section is the resolution section. The resolution must set the client’s mind at ease and tell them that the sales process and the implementation process are not complicated or difficult. The goal is to ascertain buy-in from the client on next steps and their goals and to make sure that they have the information they need to tell your story when you are no longer in the room.
In order to foster an environment where sellers approach interactions in the way we are discussing above, we need to spend more time training on questions to ask, insights to bring, the ability to paint a verbal picture of the current reality for clients, and the ability to paint a verbal picture of the client’s desired outcome. We need to consistently be talking to our sellers about bridging the gap between status quo and desired outcome, not the gap between problem and solution. The path between problem and solution is paved by facts and information, while the path between the status quo and the desired outcome is paved by human obstacles, the fear of not overcoming those obstacles, and the hope of ending up in a better reality.
Dan Greenberg · September 4, 2025 · 8 min read
Back in fall of 2023 I wrote a piece on storytelling in sales. The idea was, and is, that sales is decidedly an art and not a science. We are connecting to people, and having human interactions, so the way we go about our jobs cannot be mechanical and by rote. We have to be creative. That said, we have to do our job over and over again, and even the most creative people in the world need systems and processes to support their creativity. I walked through a 4-step process for building stories and thinking about how to use them in client interactions.
I mention that article because it is a good reference point and goes well with this post, and two of them combined are designed to help think through how to decide what materials need to be created, when those materials should be used, and then how to create them.
Here is a link to the article for reference: Article
There are four matrixes of creating external facing material:
The four step process that I reference above can be used for the creation of all of this type of material, and in fact, should specifically be used to create one foundational story that can be developed into each version of the material that you need to create.
The four steps of your story are:
a. Intro and hook: In this part of the story you earn your right to be part of the conversation by way of introduction, and you gain commitment from the buyer to be engaged.
b. Problem: In this part of the story you triangulate and establish agreement with the client on their problem, and its effect on their business.
c. Solution: In this part of the story you triangulate and establish agreement with the client on their desired outcome, the type of solution that would bring that outcome about, and the value to their business.
d. How to: In this part of the story you build a plan with the client for how to move to the next steps of the interactions and agree on an understanding of what the goal of that next step should be.
Matching up different sets of material and types of pitches is extremely important to your sales process because it pays heed to the fact that you cannot close complex or relationship based deal in a single interaction. There are different stages, different people, and different goals that need to be addressed. Being aware of what version of your story, and what type of material will be most appropriate for different scenarios will help you be more effective, and more efficient with your own time.
There are a number of ways to think about different types of material. For example, Daniel Pink, author, speaker, and sales influencer, who I have referenced before in my writings has his version. His version looks like this; The One Word Pitch, The Question Pitch, The Rhyming Pitch, The Email Subject Line Pitch, The Tweet Pitch, and The Pixar Pitch. He is, of course, thinking about the early part of the funnel and how to attract, and secure conversations, but the point is the same. There are different needs for different scenarios, and thinking about those needs ahead of time so that you can apply your core, and fundamental messaging to different versions of content is very important.
As Pink explains it, “The purpose of a pitch is not necessarily to move the catcher, it is to provide something so compelling that the catcher becomes a collaborator, and wants to help shape the pitch”. What this means is that you are not trying to sell when you talk to the “catcher”, you are trying to persuade them to work with you. And what that means in regard to the matter at hand is that there will be more interactions and fundamentally different types of interactions and we need to be prepared for them.
So let’s discuss that foundation in a bit more detail. If every interaction is an opportunity to tell a story, it is a good idea to have basic stories built out that suit all the various most likely situations that you will find yourself in. There are essentially 4 ways to think about the different situations you can find yourself in, and these are them:
The trick is to remember that the presentation is not the slides. The story that you tell is the presentation, and the slides are just one iteration in aiding that presentation. You should be able to do your entire slide based presentation without a single slide. Further, you should be able to tell your story in 15 seconds, 30 seconds, 1 minute, 5 minutes, 10 minutes, 20 minutes, 30 minutes, 1 hour, and 2 hours. Once you know how that story is told in all of those time frames, then it is time to create presentation aids like slides, videos, props, and handouts that make the story come to life.
What we are trying to avoid here is the classic template deck where sellers frantically pull slides from a prior presentation or a template into a presentation and then mix and match them to fit the current situation. The problem with this method is that it starts from the slides and then fits the story to those slides. This could work from time to time with a good storyteller at the helm, but to get it right consistently we need the story to lead and the slides to come second.
A 15 minute version of the story may not include information about certain insights and research that would add to much time to the presentation, but it may include a singular slide that walks the clients through all of the problems that the status quo causes for other clients and helps the seller launch into a quick version of discovery that will give them enough information to proceed. However, if the template deck includes a number of slides on the problem, and in order to run discovery the seller decides to use them all, they may not have enough time to work through the rest of the story. Similarly, longer presentations should involve more detailed product and feature descriptions, but short, and earlier stage presentations will likely involve a single and simple high level overview to replace all of that detail.
The idea is to look at the four matrices and select the 6–10 scenarios that you will find yourself in the most often and create the story versions for those situations. Don’t forget, this includes things like sendable takeaways, and insight based one sheets. Email and call follow up are types of interactions, and should be thought about as versions of your story as well. Once you have written those stories, it is time to create some materials to match them, and to make your presentations come alive.
It is not that having a template or repository deck is, in and of itself, a bad thing. In fact, once you have done this you should create a template so that each time you find yourself preparing for a new type of interaction it is easier to creates a new story and compliment it with materials, but the caution here is to make sure to write the story, whether it is as simple as a paragraph for an elevator pitch, or a line for a one-sentence takeaway, or as complicated as an interactive, dynamic experience for the client. First write the stories, then fit the materials to those stories.
Dan Greenberg · August 21, 2025 · 5 min read
The concept of social proof is talked about quite a bit by sellers, marketers, sales coaches, and executives. We all have a basic understanding of what it is, but we don’t often spend enough time reflecting on how to execute on it in a way that is influential with our prospects.
It is human nature to want to be one of two things; either a trendsetter, or risk averse. Being a trendsetter means that you are a tastemaker and others are following your choices. Being risk averse means that you would like to know the outcome of everything before trying it. The drive to be perceived as a trendsetter is strong but it is very heavily related to personal goals and visible manifestations of social currency like style and taste. This means that when it comes to a business setting, this drive can become a bit more muted. At the same time, risk aversion becomes more dominant in business settings because people’s careers are held dearly, and the potential of losing face, or losing status, or even losing a job is seen as very traumatic, and rightfully so. For these reasons and others, risk aversion becomes a dominant factor in decision making in the business world.
Since people cannot see the future, and cannot understand how decisions will work out, the only way to make any reliable, or seemingly reliable decisions based on an understanding of how things may work out in the future is to look at similar situations and understand how they turned out in the past. We have been conditioned to look for comparable scenarios in order to judge our own, so the idea that someone else going down a path similar to the one we are considering had success with a specific solution or failed with that solution is going to inform us very heavily one way or another.
Buyers will say that they want something custom and brand new. Asking for something new and custom sounds desirable, and it also sounds good in a professional setting so it can be sued as a tool by the asker to improve internal status. In other words, “Hey guys, look, Im making the vendor bend over backwards for us, look at my negotiating skills”. However, what the buyer really wants is that you be completely dedicated to them and think about their problem exclusively. They don’t really want a custom and new solution, they just want you to treat them like they are unique. The reason for this is what was explained above; trendsetting takes a back seat to risk aversion in business settings.
That is why they all ask for case studies. They want to peace of mind that what they are about to buy has been tested, and works, and will not surprise them. They want to be able to tell everyone at the buying organization about the cool new thing they are doing without assuming any of the risk of doing a cool new thing.
Sound unreasonable? Sure it does. Is it solvable? Sure it is. Your decision maker, in a one-on-one setting needs to have risk assuaged, and your larger group settings need to convey excitement and newness. But more importantly, there is one mechanism that can bridge the gap between both, and should be used consistently but smartly, and that is social proof.
Talk about other clients who are similar to them. Talk about those clients’ problems so that they can identify with those clients and their problems. But here is the key; don’t talk about the solution. Talk about the client. Talk about how you consulted them on the issue and the desired outcome and how that was fulfilled. Don’t talk about the details of the solution. Sure, if you get asked a question about it, answer it, but then move quickly back to situation, problem, outcome and value.
When you talk about the solution, you are telling the client that they are not getting something that is custom built for them. Sure, they know that, and they even want that, but when you call attention to it, it gets talked about and your decision maker loses the ability to talk about the great new thing that they are doing. However, when you talk about the situation, and the problem and the consultation, you help your client identify with someone who has solved the problem, and you increase your own value as an advisor who can help them navigate. When you talk about the outcome and the value, you help your client envision a world that is better than the status quo so that they can get excited about a solution, while at the same time you are helping assuage worries about risk.
Dan Greenberg · August 4, 2025 · 6 min read
Have you ever found yourself thinking something along the lines of, “I better make sure to tell them about everything we can do, because what if I focus on one thing but it turns out they want something else; I might lose the deal”. I know I have done this. It is the most human of all things to do. It is a hedge, it is a way to give ourselves assurance that we have checked all the boxes and taken all the action that we could possibly take. As humans we tend to be risk averse. We tend to want to cover all of our bases and make sure that we have done everything we can. The only problem is that the “doing” is often the wrong thing to do and it can be a waste of energy, or worse, it can have adverse results in terms of what we are hoping to accomplish.
I work with a lot of companies who tell me how great their solutions are and how every company can use them to improve efficiency or cut costs, or do whatever it is that they say they help with. This may or may not be true, and it may or may not be a good message to investors, but I can tell you one thing for sure, it is not a good message to clients. If you are perceived to be giving off the message that you are good at everything and a good fit for everyone, you immediately lose credibility.
These business leaders are doing exactly what I described above. They are hedging. They are trying to position themselves to take all possible actions, and to not leave anything on the table. But the message they are sending to potential clients is that they are trying to win their business, not that they can solve their problems.
I consulted for a small services business once, and the owner of the business could not stop telling me how good his products were for all these different types of businesses (insurance companies, broker/dealers, banks, investment originators), and he wanted to use messaging like that in his marketing because he was worried that if one of the segments noticed his ad and didn’t see their industry, he would miss that opportunity. The problem is that everyone sees that message and thinks, if you are good for everyone, then you can’t be focused on me.
Similarly, I once worked with the owner of a logistics company. I was working with him on his go-to-market messaging and he told me that businesses of all sizes should use his logistics services because he can do everything FedEx does, but he can do it cheaper. I told him that the first thing that would pop into my mind if I heard that claim would either be: “then why aren’t you as big as FedEx” OR “then why hasn’t FedEx been forced to lower their prices”. It simply doesn’t matter if the claim is true or not, it does not have credibility.
Business leaders, and sellers are equally affected by this FOMO (fear of missing opportunities). Sellers often try to offer every product they can sell, to every client out there, for every situation they encounter because they worry about missing an opportunity if they impose scope limitations on themselves. I know this partially because I used to think this way.
Don’t fall into the ‘everything for everyone trap. Focus on what you do best and focus on the client you service best. Be extremely clear about what you are good at and stay on point. If you try to offer your clients a menu, they won’t pick anything because they are simply not mentally engaged enough to do your job for you, which entails thinking through their issues and slotting your expertise into their needs puzzle.
Be really clear about what you are good at, and don’t be afraid to say what you are not good at. Tell your client or prospect something you are bad at. Make a joke about it; tell them, “if that’s important to you then you should buy that from our competitor”, and name the competitor. This does two things. Number one it shows that you are not scared to bring up or compete with your competitor, and that you feel comfortable with your solutions and your place in the market. Number two, it gives you credibility when you tell them what you are good at.
Of course, when you are talking about your competitor being better than you at something you want to be smart and engineer the situation where you are talking about something that is not what you want to sell to the client. The key is to look for these opportunities because when you have the chance to position your competitor as being better at something, and effectively turn down work, when you are able to shift the conversation to what you really want to sell them, they will trust you more.
Companies must define their expertise and differentiators, and then define their target market clearly. It does not have to be small, but it has to be well defined and explainable. Then sellers need to take those definitions and further define their ideal customers, the situations where they can be most helpful, and the specific solution that they want to sell to each customer in each situation. Sellers should never be selling solutions, they should be selling one solution that fits one situation. If you spray and pray, in other words, if you try to convince your client that you are good at every solution in every situation just to make sure you don’t miss any opportunities, they won’t trust you on any of it.
For what it’s worth, there is an entire billion dollar industry built around this concept, and that is the auto insurance industry. Progressive’s Name Your Price tool seems like a benefit for the customer, but what it does is allow Progressive to gather information and decide if you, as a driver, fit their defined customer target. If they decide that you do, then they get to tell you that not everyone is a fit for them, but that they focus on customers just like you and have the best offerings for your situation.
Dan Greenberg · July 15, 2025 · 6 min read
Tell someone you are an expert and they will listen and disregard the risks of listening.
For long time readers of this blog, you may recognize this reference, but back in 2014 there was a show that aired called “Mind Games”. I highly recommend it for anyone interested in understanding human decision psychology.
My appreciation for the show was clearly a minority opinion as it was discontinued after only 5 episodes, so if you’ve never heard of it; I understand. The show starred Steve Zahn as a behavioral psychology genius with social anxiety and other behavioral problems of his own. The co-star was Christian Slater, who played a possibly reforming former criminal, employed to help leverage his brother’s (Steve Zahn’s character) skills and keep his less helpful traits in check. Each of the episodes featured a “consulting” team who were hired to help influence an individual or group to do what a specific client wanted.
There is a specific episode that I want to reference for this article, because although the show was pop culture, the human behavioral psychology is sound, and it is very relevant for what we are talking about here.
In the episode the consulting group is working with a client who wants to persuade someone to take his side in a corporate disagreement. The details of the disagreement are not even important because the advice is so simple that it borders on inane. The advice given to the client is to start the conversation by calling out the fact that he is an expert in the subject matter.
Telling someone you are an expert makes it more likely that they will listen to you. This is so straightforward that it almost feels like it is not worth mentioning. But so many people don’t take advantage of the device, that it certainly is worth discussing.
Of course there are a few caveats here. The claim has to be believable, it has to have appropriate scope, and the claim has to be made in a setting that allows for it to be received in the right way. First, the claim has to be supportable by your history, background and ability to converse about the subject that you claim to be an expert in. If the claim seems dubious, you will lose face.
Most sellers are experts in the industry that they work in, and only you know if you are, but learning enough to be able to support that statement is important, and if you are one, don’t be afraid to use the term. Second, the claim cannot be so inclusive that you have essentially told the client that everything you say going forward has to be believed. Make sure to define the boundaries of your expertise in order for the claim to be perceived as credible. Lastly, make sure to make the claim at a low tension moment well before any sort of disagreement seems to be coming to a head. If your claim is perceived to be a tactic to win on a point, it will likely be received poorly.
Telling someone you are an expert in a specific area is not a one-way ticket to always getting the result you want, but what it does is diminish the risk the other person feels in listening to you. Much of the job of a seller is to de-risk situations for buyers so that they feel more comfortable moving away from the status quo, and perception is reality. So, if the buyer feels more comfortable with your expertise, then the situation will seem less risky.
Perhaps more importantly, and sellers don’t do this nearly enough, you should be going out of your way to find opportunities to call others on your team experts. The claim of expertise is even more credible when it is made about another person. So, if you can credibly call people on your side of the table experts, it will be believable, and will do just as much to help buyers feel like there is less risk.
Call your account manager an expert in platform strategy and use-case decisioning; call your sales engineer an expert in implementation; call your product lead an expert in the industry landscape. Don’t be squeamish about using the term, so long as the claims are credible.
So, why is all of this relevant? Well, claiming expertise in a credible, defined, and relevant area is half of the act of giving up power, which we have discussed in past posts. In defining the scope of your expertise, you should be thinking about those on the other side of the table and what that leaves for them. By defining your expertise credibly, you are giving yourself license to take control in the matters that are governed by your expertise, but you are also defining the situations in which you should give up a bit of power and allow the alpha on the other side of the table to have their few minutes in the sun.
This is not only something that individual sellers should be thinking about, it cuts to the core of how selling organizations should be thinking about defining their go-to-market approach and their definition of expertise. Companies consistently make the mistake of defining their capabilities in the market too broadly. When they do this, the client becomes suspect immediately, and evaluates that claim against all other claims about broad expertise. However, defining expertise in a very focused way allows sellers to develop credibility and productive conversations with buyers.
Selling organizations should be thinking about how to limit the scope of their definition of product market fit; they should be thinking about limiting the scope of their definition of content and collateral, and they should be thinking about how to limit the scope of their training which allows sellers to display credible and focused input for their clients. This will allow sellers to operate in a world in which clients want to talk to them.
Here’s how to think about it: it’s not that clients will listen to you about everything, but defining expertise will help make clients forego the risks associated with taking your advice if you have positioned your expertise in the right way.
Being an expert only matters if the definition of your scope of expertise is:
Dan Greenberg · July 3, 2025 · 7 min read
Your prospect is always busy. You are always interrupting them any time you make an unscheduled or cold call. Whatever the prospect was doing before you called is what they chose to do, and therefore deemed most important. So yes, you are interrupting them. Because of this, the client will always be predisposed to object whenever you call them unscheduled. It is important to understand what these types of objections are. They are routine based objections. They are a human’s internal gatekeepers making up a reason to disengage and keep the easily distractible human on track and away from distractions and new activities. This is human nature, but it is important for sellers to understand because it informs how we should deal with them.
The first thing to understand is that these objections are not rooted in anything substantive, so while it is good to have a plan for how to deal with substantive objections, handling routine based objections is much different. There are two key components to dealing with these types of objections, and one has to do with how to avoid them, and other has to do with how to handle them.
Let’s start with the former. The success of your unscheduled client call, or cold call is highly dependent on the first 20 words that come out of your mouth. If you leave an opening for the buyer to ask you a simple question, like; “Who are you?” “What do you do?” “What’s your name?” “What company?”, you will have put yourself in a tough position. You will now be on their agenda, responding to them and following their lead. Down the road it will be important to get your client to ask you questions. However, at the very beginning, you want them listening to you so that you are in control. The person who asks the questions controls the conversation.
This is why it is important to state your full name, your company name and the reason you are calling very clearly and succinctly. Then you want to state their problem better than they can. Since you are likely on a cold call, of course, you want to get buy in that they are experiencing the problem that you are stating, but that only comes after you have been clear about who you are and why you are calling.
It is also very important to realize that you are selling yourself, or your sales partner, if you are an SDR. It is your job to sell yourself so that the prospect decides to spend more time with you. Notice that nowhere above does it talk about your products or solutions or how you solve problems, none of that is part of the equation.
If you clearly state who you are, why you are calling, your understanding of the prospect’s problem, and you focus on selling the next meeting, rather than the product, you will get far fewer routine based objections, and you are likely to retain control of the call. But of course, you are still likely to get some pushback.
So, let’s talk about the second component of dealing with routine based objections. You will get many types of objections on early stage calls, and they will often come one after another because your prospect may be on autopilot for large portions of your call having not yet committed in their mind to devote any time to listening to you. Let’s go over a few and some thoughts on how to handle them. These are not the only ways to handle them, but they are thought starters for use and incorporation.
“Please call me back in a few months, that will be a better time to discuss this”
Seller’s response: “Why three months? Whats happening then? why will it be a better time?” OR “What is it about your business that is changing that will make 3 months from now different?”
The buyer led the seller to this line of questioning so they will feel compelled to answer the very-on-point follow up question, but answering that question will make the buyer think about if a few months down the road really is better timing, and give the seller the opportunity to gather more information.
“We can’t consider this until after next year’s budget planning”
Seller’s response: “Budget planning can be a task, I just went through that over here. I know things can get lost in the shuffle in those types of scenarios, and I can help you prepare the internal ask well in advance. How about getting started on the conversation so that you can wrap your mind around exactly what you need, and see if we can provide it so that by the time budget planning comes around you are all prepared?”
This is a tricky one, and it is important for the seller to be sure to signal that they will not be putting pressure on the buyer to make a move until after the budgeting process. Alternatively, the seller can remind the buyer that their procurement and process may cause delays, so if they think this could potentially help their business, it would be a good idea to get the process started now, knowing that nothing can get to the final stage until after the budget decisions.
“I have to think about it, just send me an email with some information on your solution”
Seller’s response: “What exactly would you like to see in that email?” OR “I want to make sure to send you only the most relevant information to save you the trouble of looking through things that are not important to you, can you share with me a little bit more about what issues the problem is causing for your business, and what you would like to see change in an ideal outcome?“
This line of conversation can be a bit tricky because it can be seen as pushy, but oftentimes the response will just be something to the effect of, “just send me an overview”. In these cases, you can offer a video call and walk through at a later date to help them process what you send them. Either way, make sure that the tone is different when you make these requests so that they don’t suspect that you are just trying to drag out the meeting and waste their time. Signal to them virtually, or otherwise that you are wrapping up and that you will send them something.
“I’m not interested”
Seller’s response: “Sounds like you already solved X problem. I would be curious to hear how you are approaching it.”
This will either lead the prospect to explain to you how they have solved it, in which case you can probe for additional problems to solve, or more likely, it will prompt them to equivocate and say that they haven’t solved it completely, or they put it on the backburner and are focusing on other issues, or something like that. Either way, it creates an opening to ask one more question, and that is all you need sometimes.
The takeaway is that objections are not rejections, and thinking about how you will respond to objections before they happen allows you to stay calm and often earn the right to ask one more follow up question, and that could make all the difference between a rushed hang up, and a scheduled call with the prospect.
Dan Greenberg · June 20, 2025 · 7 min read
Calls with prospects and clients that occur early in the buying process can be tricky to manage. There is no defined path or working plan yet, and often times the rules and dynamics of the relationship are still being sorted out. It is important to have a plan going into these calls. Regardless of if you have slides or not, you are telling a story, and the part of the story where you unpack the clients problems and their effects on the client’s business is the most important part.
These calls should be close to scripted so that you can be sure of where you are going and how to get there. This doesn’t mean that you have to or should stay on script at all times, but it is important to have fully baked language, a plan, and talking points so that you can stay on track. One of the easiest ways to define the steps of a call like this is by using the 4-part story device that I have talked about in earlier articles. You should have a number of different versions of your 4-part story, and you simply pick the proper one for the particular interaction you are having. Once you have established an agenda with the client, preferably prior to the call, you will simply start your 10 minute version, or your 20 minute version, of the story, or whatever makes the most sense for that particular meeting.
In your 10, or 20, or 30 minute version of the story, especially in a very early stage meeting, you should have a few goals that are very specific.
In part one of the story, you must revisit your research or insights, and earn enough credibility to justify the fact that you have just moved from taking about 1 minute of their time, on a cold call or in an a message, to now talking about 20–30 minutes of their time. Your goal is to prove that you belong in the conversation. Use social proof if you want, but who you work with does not make the case alone. You have to state a point of view and something insightful that proves that you belong in the conversation, and that you, as an individual, are worth their time.
In part two of the story you should expand your discovery with the goal being to understand how the prospect describes and thinks about their problem. The goal is to come to an agreement on problem definition that makes sense as the foundation for the continued conversation.
In part three of your story you should discuss desired outcomes with the goal being to let the client know that there is a path from problem to outcome that is value positive for them, but you should focus on talking about your solutions as little as possible.
Lastly, in part four of your story your goal is to establish next steps, gather validation on your understanding of the problem, and establish the goals of your next interaction with the prospect, who should be involved and what it should look like.
This early stage interaction can occur on the cold call itself, or on any subsequent call early in the buyer’s journey. Regardless, unless you are in an extremely transactional and non-consultative setting, you are NOT selling your product yet. You are establishing credibility, understanding and validating the problem, learning about the desired outcome, and gaining momentum by gathering your first set of agreements from the prospect so that you can move on to more.
This type of mindset takes patience and resilience. You will get multiple objections, which should not be taken as rejections, and beyond that, you will not be able to close a deal early in the process. Both of those are not only OK, but they are necessary to give you the best opportunity to close down the road. The initial calls are meant to set yourself up for calls down the road. If you pitch your product on the first call, or before deep discovery it is impossible for the client to believe that you have taken their specific problems into account when you do present your solutions. Just think about it for a minute, if you do discovery, and then immediately present solutions, how could you have taken your discovery into account when building the presentation. This means to the client that your presentation was premeditated and not tailored from them.
Clients will however, make it hard for you to do this. They will say things like, “Just show me the slides so I know what you are offering”. But, asking questions and having a real conversation about the client’s problems is better for the relationship, better for the likelihood of a deal, and better for the client as it can align you better with their needs. The default action for the client will be to push you to present and leave so that they can use your presentation information to help make a judgement without having to engage with you, in the moment. It is the same human nature that causes us to text instead of call, and to avoid talking to the human when we can place our order online. You buyer is like everyone else. They want the info now in order to engage later.
The problem for you is if they don’t engage now, they are not actively deciding while you are interreacting with them, so your opportunity to be influential will suffer. That is why it is so important for you to ask the right questions that help you challenge the buyer so that they do engage and move down the decision funnel while you have the opportunity to be influential. The only way to do that is through questions, so let’s talk about good questions for calls early in the buyer journey. I am going to use the SPIN selling methodology (Neil Rakham) for this exercise because it is an excellent way to think about question progression. None of these questions are meant to be asked as is, they are ideas of the types of questions that should be asked in order to encourage your client to truly engage.
Understand the Situation:
Your goal with your first set of questions is to establish the situation, and a shared understanding of it. In forget to earn the right to ask questions, and to make the client feel good about sharing with you, you will have to reestablish credibility again as part of this question, but reiterating your information or insights that show that you can add value to the conversation.
Learn about the Problem:
The goal with problem questions is to establish a shared definition of the problem(s) that is both cathartic for the client to talk about, and commercially viable for you to spend time on.
Understand what is Inferred by the problem:
The goal with these questions is to broaden scope and more fully define the problem in a way that develops an understanding of how it truly effects the ability of your client firm to operate.
Understand the value equation / Need Vs. Payoff:
The goal with the final set of questions is to learn from the client just how important the problem you solve is, and simultaneously to start developing, in your client, their own entrenched belief in its importance.
Dan Greenberg · June 6, 2025 · 9 min read
“Nobody picks up the phone anymore”, “You can’t reach clients on the phone”, “The phone call is dead”. Psht…give me a break. People say this because they don’t want to pick up the phone. They are scared. I’m not saying that as a put down, I am scared too. I have been in sales for 20 years and I am still scared of picking up the phone. I can do it 50 times a day, and that 50th call is scary. Rejection is a scary thing. This is bread into us evolutionarily, because historically, rejection from the tribe or group meant almost certain death. Rejection, and the possibility of rejection is one of the scariest things we encounter in our lives, and worst of all, we can’t talk about it or act like it’s a problem because it is emotionally scary, but not intellectually scary, so it seems socially unreasonable to complain about.
For this reason, many people look for and find justification for not making calls. Calls are live and real time. It is a lot easier to brush off a rejection in an email than to hear someone directly tell you that you are an idiot, or annoying, or to never call them again.
But the reality is that phone calls work better than they used to, provided that you do good research. Every phone call used to involve reaching a machine, an answering service, or a gatekeeper of some sort. But now, many buyers don’t even have land lines and they just use a mobile phone as a work phone. Not only that, but many sellers have abandoned calls, so buyers, while getting many more emails than they used to, are getting far fewer calls. Well crafted voicemails, and calm, simple, and direct phone conversations are a very powerful tool and should be used often in the early stages of the sales process.
Phone calls won’t work every time, nothing does. And, they won’t be the most effective strategy for all clients, nothing is. But, they are very effective for many clients out there, especially for the ones who are least likely to respond to email and messages. Phone calls should be built into every cadence so that prospects receive email, other messages, and phone calls (including VMs). These actions drive familiarity because when a client hears a name and a company from multiple forms of communication it tends to speed up the recognition and association process.
So let’s talk about the cold call itself. When you get a potential buyer on the phone, you have very little time to engage them to the point where they will not flag you as a waste of time and refrain from truly engaging with you; usually about 15 seconds.
Calls are different than emails because the goal with an email is simply to resonate and prepare for later engagement. The call, like a meeting, or an elevator pitch is a two-sided social interaction focused on conversation, and is similar to a presentation. In other words, in the first 15 seconds of a call, the goal is to engage the buyer enough to get to the next part of the call. In order to do this, you have to be engaging, clear, and get directly to the point. The only difference between a cold call, and a meeting or a presentation is that you have a fraction of the amount of time available to make your point. Even on a cold call you are still telling a story, and having a social interaction. Here is how to construct a story for the first 15 seconds of a cold call.
Here is how it looks altogether, feel free to substitute your wording for mine, and try to do it slowly, calmly, and with command, but in about 15–20 seconds:
“Hi Chris, this is Dan Greenberg from DG Consulting; we published the study that I sent you on sales training inefficiencies and their causes. Many FinServ small business leaders that I speak with express significant difficulty finding and ramping good sellers. We help with both. I’d be happy to discuss in more detail with you”.
At this point the client will object, and that is a good thing. In fact, the more foundational and to the point the objection is, the better. If they say things like, “I’m worried about the value trade off because we have internal systems designed to do this work”, or “We have struggled with implementations of tools like this in the past due to our regulatory system”, those objections are great. They open the door for further conversation and send you off in the right direction on your discovery journey. They also mean that the buyer is engaged, and thinking about the problem and solution rather than on autopilot.
Most likely, however, you will get objections like this, “I don’t have time to discuss this now”, or, “Can you call me back next quarter to discuss? that will work better.”, or, “I’m not interested”, or, “send me an email about this and I’ll get back to you”. These aren’t as good, but they are OK as well. The point is that when you get an objection, it is an opening for you to launch into discovery, and if the questions are asked correctly, that will open up more opportunities for sharing insights and research, and learning more about how your prospect thinks about their problems.
The other option, of course, is that they ask you a question, or simply agree to discuss in more detail or set up a meeting. If they agree to set up a meeting, you should nail down the time right away by offering up multiple options and making it easy for them to pick one. You can even offer, again, to continue the conversation right now, but give other times as the secondary options. If your client really doesn’t want to talk right now, this will make the secondary option sound very appealing. If the prospect asks you a question, or agrees to speak in more detail, you should immediately, assumptively take that as an invitation to start your first meeting with the prospect.
Here are the basic takeaways that should be top of mind every time you think about an early stage pitch and every time you construct a cold call pitch, script, or plan.
Dan Greenberg · May 20, 2025 · 9 min read
I have spent that past couple of posts talking about email, and specifically cold email. Although the likelihood of success with truly cold email is decreasing due to ESP server filters, and oversaturation of inboxes, email is still a highly valuable tool, and can be leveraged throughout many stages of a sales cycle.
I want to take the time in this post to dive into some specifics around email, and to inspect some of the ways that we construct sentences and choose words, so that we can think about best practices around email. This is not specific to cold emails, it is more of a thought process for any early stage client email, where much of the thinking can be used to build emails, whether they be cold or not.
Before we jump into construction, let’s note four things that are highly relevant and should be thought about whenever creating an email:
OK, with the notes above in mind, let’s take a look at an example email from a fictional rep selling CRM tools at a fictional company called Revenueforce, to Nonprofit clients:
SUBJECT: Follow Up
Hi Pat, I hope you are having a great week. Did you happen to catch us at the NTEN conference last month? I sell CRM solutions for Revenueforce which have been proven to improve operations and fund raising capabilities. I am reaching out to you because I heard that you showed interest in our solutions after the conference. I think we could really help your business out. Customers like ABC Corp love us. Would you like to set up a time to meet?
Commentary:
I’m not sure if you were catching on as you read this, but this is the prototypical example of what NOT to do. Sure it seems basically professional and decently put together on the surface, but let’s take a look at how the buyer’s mind will likely perceive this email.
Seller: “Hi Pat, I hope you are having a great week”
Buyer’s subconscious: Really? You do? I don’t really know you very well and you don’t know me, sure that’s a nice enough thing to hope for but I’m pretty sure you don’t really care unless I indicate that I have money for you.
Seller: “Did you happen to catch us at the NTEN conference last month?”
Buyer’s subconscious: I was there, but I really don’t care about your booth. I spent very little time with vendors because I was there to network and speak with piers.
Seller: “I sell CRM solutions for Revenueforce which have been proven to improve operations and fund raising capabilities.”
Buyer’s subconscious: Proven? I’m sure you have a decent product and you are going to tell me why it’s the best for some customers, and then your competitor is going to tell me the same thing and why theirs is the best for other customers. I don’t have time for a he said she said.
Seller: “I am reaching out to you because I heard that you showed interest in our solutions after the conference.”
Buyer’s subconscious: So basically, I made it onto some list? That’s pretty vague but ok.
Seller: “I think we could really help your business out.”
Buyer’s subconscious: Of course you do. It’s your job to say that, but based on what? You haven’t really told me anything that would help me understand why.
Seller: “Customers like ABC Corp love us.”
Buyer’s subconscious: I’m sure a lot of customers like their current solutions, it doesn’t mean it’s any better than another solution that another set of customers likes.
Seller: “Would you like to set up a time to meet?”
Buyer’s subconscious: I do not have time to deal with another potential vendor right now, and I’m definitely not taking my time to set up a meeting.
In order to inspect what went wrong above, let’s write the good version of this email. Remember, just because it is better does not mean it is a panacea or that it will work all the time or even much of the time. But, if you are getting a response on only 2% of your emails and you improve to 4%, that is a 100% increase in your efficiency.
SUBJECT: <colleague name> told me that <X> is a big challenge at the moment
Hi Robin,
NTEN recently published findings in its Nonprofit Technology Guide that help define and quantify efficiency waste for nonprofits using older CRM software for development programs.
We speak with clients consistently about how efficiency losses hurt their programs.
I’d be happy to discuss efficiency improvement through technology.
Please let me know if you can catch up next week.
Commentary:
The email above does a number of things better than its inferior counterpart:
If we went through the same exercise on the second email as we did with the first we could absolutely come up with pithy and annoyed responses from the buyer’s subconscious there too. It is virtually impossible to write a commercially viable email, as a seller, that does not run that risk. Afterall, the buyer is conditioned to have that reaction. The point is to go from 98% of readers dismissing you due to indifference or annoyance to 96%.
The “good” version of this email is an example of an email that would be sent very early in a cadence and very early in the lifecycle of a client relationship; likely first or second. This email could be followed up on in a number of ways. First, a seller could, and should, send more teasers and information about the research that furthers the intrigue. Second, the seller could, and should, send versions that more explicitly ask for brief calls and/or meetings. In these versions the seller can propose times and dates to make it easier on the client to simply select from them. Third, the seller could, and should, send additional research and insights that are relevant. Lastly, the seller could, and should, send versions that focus on other iterations and descriptions of the problem.
As selling organizations and sellers themselves build out email cadences and messaging plans for specific clients it becomes impossible to talk about what every possible iteration and strategy could look like, but the principals above work for early stage emails of all types.
Dan Greenberg · May 8, 2025 · 7 min read
The goal of a cold email is not to sell.
The goal of a cold email is to inspire introspection.
The goal of that introspection is interaction.
The goal of that interaction is to start a conversation.
The goal of a conversation is to find a problem.
The goal of finding a problem is to book a meeting.
The goal of a meeting is to do business discovery.
The goal of discovery is to set up a mutual action plan.
The goal of a mutual action plan is to organize the process.
The goal of a sales process is to guide the buyer through their decision.
Most sellers make the mistake of selling right away. That is what causes buyer resistance and rejection, and that effect can play out in an early meeting or in an email in much the same way. When you send emails or make cold calls remember that your job is not to sell, it is simply to inspire consideration and get a reply. So how should we think about doing this?
Let’s start with the subject line. Subject lines should be emotionally charged and compact. They should be about 3–4 words, and they should let the buyer know that you speak their language. The subject line should focus on the pain points that your specific recipient is likely to talk about on a day-to-day basis. Put yourself in the position of your buyer, being responsible for the things your buyer is responsible for and think about the words you would use to describe your issues if you were in their shoes. There is somewhat recent data that suggests that statements perform a bit better than questions, I believe this is due to overuse of the latter, but it is worth A/B testing the two. The point, however, is to write your subject line, and your email, for that matter, as if it were an internal email to a business partner rather than a sales approach. Use names of mutual people you know; people in their department that you have emailed. Use terms that are familiar to your buyer. One the other hand, don’t use gimmicks. ALL CAPS, lots of punctuation!!!! and other gimmicks will trigger the reader to think of the email as a sales approach, and that will not help your chances.
As for the content of the email itself, it should be short, entertaining, and engaging. Be respectful, informal, and familiar. Your job is to remind them that they have, in fact, heard of you, even if it is just from prior cold emails you have sent. Your job is to remind them that there is a level of familiarity between them and you. Use their terms to describe their problems. Research their company so that you can use their department’s name and even names of people they work with. Write the email as if you are talking to a peer but remain respectful. This type of content is reusable, and repositionable and can go a long way to driving recognition, and association.
Make sure that your email does not ramble. If you attempt to make a single point and ask your prospect to do one single thing you may be successful, but as soon as you try to make more than one point, or ask for more than one thing, the task will seem daunting, and you will almost certainly be unsuccessful. A good cold email, or for that matter, any message to a client, has four parts:
Let’s talk a bit more about calls to action. Sometimes a call to action can simply be for the client to watch a 30 second video or take a quick look at an infographic or a one-sheet. Your emails can always be followed up with additional emails with more commercially beneficial asks. For the purposes of early-stage emails, educational content, positioned well in an email, can be very beneficial as part of a sequence or cadence. This is because the ask is very low lift for the buyer and easy to comply with. These types of asks are often very helpful because they establish baseline compliance which establishes a bit of buy-in to the process and helps you build more momentum towards more consequential, and commercially viable buy-in.
Typical response rates to cold / early-stage emails are very low, but you don’t need me to tell you this, you are likely experiencing it. It likely takes somewhere in the range of 100–150 well thought out emails to get a meeting. But if your emails are not well thought out, it will take many more than that. Make sure that you are always relevant and succinct, as well as entertaining whenever possible. Short and to the point wins the day, because prospects don’t want to read emails, but they also don’t want to miss something that could be THE answer, so tell them quickly and up front.
Avoid common phrases like “Hope all is well”, “Sorry to bother you”, “Haven’t heard from you in a while”, and “Not sure if you saw my last email”…Oh, let’s not stop there, there are more commonly used phrases to avoid, like “We help X do X”, “Just touching base”; get rid of all of them. These are trite and signal that you are sending a sales email like all the rest. Instead, start with credibility, state the problem, help them envision the outcome, and then make a direct and easy to fulfil ask related to next steps. Keep it all brief, and these things will show your prospect that you have done your research, and that you can add value.
Christian Krause posts a lot of valuable and highly engaging advice about sales on LinkedIn. I highly recommend following him. He likes to make two points that are highly relevant to what we are discussing. 1. Keep your email to 50 words or less. 2. Use 6th grade language; no filler words. Basically, be brief; be direct.
Most importantly, however, remember your goal. Leave your features, products, and solutions completely out of the email. You are not going to make a sale via email, so stop trying. Work on establishing familiarity and association and then procuring agreement and validation on the issue, before moving to social proof and securing micro commitments in subsequent emails. Your products and solutions have no place in any of that. Sell yourself, and your expertise, and the value of the next interaction. That should be the point of the email, and the singular and direct ask of your future buyer.
Dan Greenberg · April 17, 2025 · 7 min read
Cold Emails and messages waste your time; not because there is anything wrong with them, but because you give into laziness. I know this, because I do it too, all the time. We don’t focus our energy and write a truly thoughtful emails because it is easier to just copy and paste, or send by rote. That way we don’t have to engage our brains. But these copied and pasted messages lack relevance, and most of the time the client consciously or subconsciously will sniff out that it is copied and pasted, and disregard it. Just think about your inbox, how much time you devote to messages that are not crafted for you.
The goal of early cycle emails and messages is NOT to sell your product. The goal is to get your message noticed, build familiarity, and build association between yourself and what you solve. Your goal in subsequent messages is to inspire inbound signals, get a reply, or spark a thought process or conversation. Further down the road, your goal becomes to draw out more specific responses, and book meetings. Often this process will take some time to develop, but the key is to write emails that speak to these goals, NOT emails that try to sell your product.
Your subject line should be written in their terms. This is something that I talk about with my teams a lot and we have discussed it in this book and will continue to discuss. Communications with buyers have to be in their terms, not yours, if you want to have an impact. We tend to develop very niche languages, including descriptors and acronyms that help us define our brand, and product, and our differentiators. This is the job of good marketers because it is important to understand where you are truly the best, and truly relevant. The problem comes when we start to use those terms in our communications with clients. Clients don’t live and breathe our business, and they won’t even recognize many of the terms. Even if they can intellectually understand them, they just simply won’t put their brain through the mental exertion of defining them, and building them into the context of what they are trying to think about. Instead, they will just gloss over the term and ignore it.
Subject lines should be 3–5 words. They should be emotionally charged and they should describe the client’s problem in the client’s own terms. Your job is to describe their problem so well, that they would actually use your phrase to describe their issue internally. You will see some research that tells you that questions work well in subject lines, and they do compared to long or otherwise poorly written subject lines, but actually good research in well conducted A/B subject line testing studies suggests that statements outperform questions by a bit.
If your client is a consumer products brand and you are a packaging company you should understand your clients challenges with space limitations on grocery store shelves, and product freshness, and craft a subject line that that lets them know that you understand that there are tradeoffs and that solving one problem leads to the creation of larger issues in reference to the other problem. The subject should be written in the terms that they use to describe this tradeoff, your research should be able to give you a clue about that. Something along the lines of; “Great Packaging Preserves & Consolidates”, or “Preservation & Space Consolidation Combined!”. If I were actually a packaging seller, I am certain that the wording would be slightly different, but the idea is to use words that are used consistently by the client to define their problems. If they constantly think about consolidation of space for shelving, and they constantly worry about freshness preservation, then use those terms. Keep it short, keep it snappy, and keep it emotionally meaningful to their day to day.
Keep the email itself simple and short as well. Remember that you are not trying to sell your product. The goal of a cold email is to get noticed, and to improve recognition and association, and eventually to get a response. You should be making one point, and asking for one reaction, and you should be making it with simple language free of any terms of art or industry specific acronyms. As soon as you try to make more than one point or ask for more than one action, you will lose the reader.
There are many writers and even sales bloggers on LinkedIn and other sites who will talk about the F shaped email. This means that your first line is longer, and the subsequent lines get shorter. This is a good rule of thumb and the reason it works is because, as I have mentioned a few times in this blog, human beings are mentally lazy. This comes from our evolutionary need to limit exertion in order to save energy for the important things like hiding from lions. The way this plays itself out in this context is that people may start to read an email but they quickly decide that it is too long and start to skim. This means that they may start by reading horizontally, but then look for shortcuts and start skimming vertically. An F shaped email plays into this and allows you to get all of your major points across.
Your emails should be short. I mean, very short. They should be between 40 and 60 words. Remember that you are only making one point, and asking for one action, so if it is getting hard to keep it in that range, you should revisit the message you are trying to get across because you may be inadvertently trying to make too many points.
Lastly, add a P.S. Oftentimes in the rush to finish an email and move on, people skip to the P.S. and read that in lieu of other parts of the email. The P.S. is a way to stand out, and make a personal point without seeming pushy or awkward. They are easy to conceptualize and put into action, and they improve recognition and response rates.
Dan Greenberg · April 3, 2025 · 7 min read
We have all come across sellers whose optimism is nauseating. They are always about to close the biggest deal yet. They project monster numbers, and they consistently talk about how they will “crush their number”. Sometimes they do, and sometimes they don’t but the frustrating thing, for managers and leadership, is that they make it very hard to forecast. Managers must build in systems and checks in order to counterbalance the optimism and relay realistic forecasts. The over-optimists do tend to attract real belief in their ability to perform, but they are not seen as savvy when it comes to the business, and they have a hard time advancing in the organization.
The other side of the coin is not pessimists. Pessimists frustrate people with their lack of belief, and they cause similar problems from a forecasting perspective because they underestimate their numbers. The pessimist does not have an upside. The other side of the coin is actually the realist. The realist is perceived as having a lack of belief because they tend to predict lower projections than managers expect, but their projections tend to be closer to the truth, and their understanding of potential blockers and headwinds is usually understood to be savvy. So, while they do not tend to inspire that high level of belief, they do tend to be seen as sound organizational players who can advance in the organization when they do perform.
So, the question is which should you tend towards? The sandbagging realist, or the head-in-the-clouds optimist? The realist will often be called a pessimist because they under-forecast, but they are often much closer to the actual results than the pessimist would be. What makes things so hard for the realist is that it is in the realist’s nature to only project revenue that they can see a path to. The problem is that we cannot see a path to all the revenue that we can expect to bring in over the course of a quarter or a year. We just simply have not had all the right conversations yet. If we only projected revenue that we could see, our projections would be pretty low, and we would not inspire much hope for growth.
The problem for the optimist, on the other hand, is that they assume that every deal that is in their pipeline is likely to close. They actually have the same problem as the realist but viewed through a different lens. They cannot see the reason why they are likely to lose any deal, so they assume they won’t. For this reason, they are certain that many of their deals will close, and they end up over projecting.
It is OK to start from either point of view. If every deal in your pipeline is likely to close, you have to figure out a way to sprinkle in healthy realism that introduces possible pitfalls and headwinds, and allows you to discount your forecasts, but more importantly, become vigilant against possible problems. However, if you can’t possibly think of a world in which unlikely or unknown deals could possibly close, it is important to figure out a way to introduce a business development, or new opportunity coefficient into your calculations so that you can correct your forecasts to a more growth oriented level, and more importantly, redirect some resources and mindset to those potential opportunities which will make them more likely to manifest themselves.
The idea here is that you can start from your natural personality and mindset, but having self-awareness, and knowing yourself very well, allows you to introduce checks and balances in your own mind that will help you forecast better, but also make you a better seller, and alert you to the right ways to spend your time and resources. It is not easy to find this balance, and not everyone will find it in the same way, but it is important.
Understanding your odds of success is an important part of selling, not only for forecasting purposes, but for your own mindset as well. It is estimated that Idina Menzel and Kristen Bell each made $10M for their roles in the production of Frozen 2 last year, while the average Broadway performer, or actor is waiting tables, working towards membership points in their union, and trying to scrounge together enough money to pay rent. Patrick Mahomes is projected to make well over $200M in salary alone over the course of his likely 15 plus year career, as quarterback for Kansas City Chiefs, while the average NFL player will play for about 3 seasons and make about $3M, in total. $3M may seem like a lot of money, and it is, but remember that they have trained their entire life for the job, and will likely find themselves physically unhealthy, and somewhere around 26 years old without other skill sets necessary to excel in other fields. And all of that does not even take into account the average football player who never made it to the NFL and was never paid to play.
Are Idina Menzel and Kristen Bell 50 or 100 times better than the average highly trained singer, dancer, and actor out there? Is Patrick Mahomes, or any top athlete 75 times better than the average player in their sport, or hundreds of times better than highly trained top collegiate athletes who never made it to the NFL? Absolutely not. Sure, they may have a unique quality about them. They may perform the right role, or play the right position, at the right moment in time. They may work harder, although there are only so many hours in a day, so that effect can likely only be incremental. But they are certainly not 50, 75, or 100 or even more times better than the other highly trained and talented individuals they compete against. So, why do they make 50, 75, or 100 times more money than those other people?
Tiger Woods, at his peak, only shot 2–3 strokes better than average tour golfers at many tournaments. That’s about 4% better. Top CEOs, absent external factors, can expect to drive a company’s CAP table growth to somewhere around 7% in a great year, while average CEOs can expect something more modest, like 4% or 5%.
The sellers who are making $300K or half a million, or even a few that are making over a million per year; they are not 10 times better than the average seller. They have learned to do the little things better, and they have learned to become so consistent at those little things that they are now second nature.
Of all of your suspects, a small percentage become prospects, and of your prospects, a small percentage become leads, and of your leads, a small percentage become opportunities, and of your opportunities, a small percentage become deals. This may sound depressing, but it is exactly the opposite. It is exhilarating. It means that we just have to move the needle slightly at a few strategic points in our funnel to change our outcomes drastically. If you are closing deals with 2% of your prospects, and you change that number to 4%, you just doubled your revenue to goal and your commission.
The high earning sellers out there are not more talented, and they don’t know something that you don’t. They don’t have a special personality or demeanor, and they are not born with an ability to handle rejection that you don’t have. They have simply improved over time. They have committed to learning from setbacks, and they have made a commitment to themselves to get better each day, which adds up over the years.
They have trained themselves to control their emotions. They have learned to really listen. They have coached themselves to be attuned to social cues and to recognize what drives emotion and engagement. And most importantly, they have developed, in themselves, the discipline to set routines and systems and to stick to them.
Dan Greenberg · March 21, 2025 · 5 min read
I’ve mentioned my nerdy infatuation with the reality shows Survivor and Big Brother in the past, and I’d like to provide another reference related to those shows to help contextualize this post. Specifically, we can learn a lot about organizational dynamics, and power sharing from these shows; here’s how.
Let’s start with this question. Why do I care so much about these shows? I don’t really. I mean, they are entertaining to me. But more so than caring about the results, we can look at life as a training ground for sales, business, and organizational awareness. These shows give us a unique vantage point that allows us to get a glimpse of people’s thought processes in competitive situations, and gain some insight into how decisions are made. So much of the behavioral ability that we need in sales doubles as social skills that we use everyday in life. And, so much of the behavioral ability that we need to navigate and manage organizations doubles interpersonal skills that govern our relationships. This means that we as sellers, leaders, and managers get to learn from everything; including pop culture, and silly reality shows.
In reality shows like Survivor and Big Brother power can shift quickly based on the circumstances, and a person who had power one day can be the most likely to be voted out the next, while a person who had no power very recently can sometimes find themselves being looked to by others as the outcome decider. Most often, when people on these shows gain power, they become fixated on executing a very specific plan that they have envisioned, to the exclusion of all else. They find themselves in a position of power, and then falsely calculate that executing their own plan, including voting out the people that they believe threaten them, is the best way to hold on to that power. And sure, to their credit, if they did have perfect influence and could make sure that the exact people they wanted to be voted out were, in fact, voted out, there would be some merit to this. But that is not how life works, and there are other people with independent brains in the game, just as in life. Regardless, they push forward trying to exert maximum influence on their alliance, or within their sphere of influence, hoping to be able to execute perfectly on their plan.
As a person starts to develop power, they are in the perfect situation to strategically share power and democratize certain parts of the strategic decision making to other people in their sphere of influence. This can earn the person loyal supporters who trust that they are heard and valued by that person. Without a title, or any form of structure, power will inevitably shift again, and if the person who just found themselves in a position of power misses that opportunity to strategically share power, they will find themselves in a much worse position when they no longer hold the same level of power.
Even if they are right, and their plan is best, a suboptimal plan with buy-in from the team, that is well executed, will achieve far superior results compared to an optimal plan with limited buy-in and subpar execution. You see, the second part of the equation is that buy-in from the team actually improves results even if the plan is not perfect. It is not that people on the team all need to get their way, that is impossible, but they need to feel heard, and valued, and their ideas accounted for. If that process takes place, then the majority of people will be more bought-in to the plan and share the vision and work harder and smarter to achieve it. This will mean that even sub-optimal plans yield better results than optimal ones that are not well executed.
Basically, the point here is that sales organizations are full of very persuasive people who think of themselves as influencers and might be considered to be stubborn when looked at in a less generous light. This means that there can be a fair amount of personality clash and power struggle within these organizations, but the key is to remember that many of the persuasion tools that we use to make sales can also be used to build consensus internally, and the goal is not always to get ‘your way’, but rather, to find a ‘good way’ that satisfies the group, and can be well executed. This type of organizational operation will build social cohesion, and position a person well to lead groups and projects. So, even though sharing power may seem like a way to disperse influence, if the results are good, the effect will be increased influence.
Dan Greenberg · March 7, 2025 · 8 min read
My family is a big poker playing family, so I heard this statement a lot growing up, “Anyone can read their own hand; being good at poker is being able to read the other players’ hand”. In other words, it’s nice to have a plan, but it means nothing if the situation or the person you are dealing with changes or behaves differently than you expect them to. I was talking to a friend who is in a new sales role for the first time in her life, and she told me that she met a potential client who she was friendly with at a bar and had a great conversation with him about what she wanted to sell him. She went on to tell me that she is just going to take all of her meetings at bars. I told her, “that’s great” because it is great, but there is a “but” there. She obviously “clicked” with this guy who she is friendly with, and when we “click” with someone it is easy to develop a relationship. However, If we think about it logically, each individual will generally click with some people and not with others. So, while this approach may get you some deals, it won’t help you with other deals, and more importantly, it won’t make you any better at your job than the next salesperson who is selling a competitive product. The bottom line is that in order to be a good seller, it is vital to learn to interact in situations we are not comfortable and with people we don’t click with.
First, let’s talk about the people. As humans, we tend to gravitate towards those we click with, and sellers are no different. We should leverage those good relationships to our mutual benefit with the buyer, both socially, and commercially. But, part of becoming a great seller is learning to sell to everyone and in every situation. Your perceptiveness, and attention paid to the behaviors of your buyer is what will allow you to identify their comfort levels with certain lines of conversation, and their levels of affinity for different styles of engagement. That attention, and perceptiveness will help you to understand when to be a Gitomer, which means focusing on the positives; the vision and hope of the buyer, and when to be an Orlob, which means focusing on the buyers pain (see “Pain & Hope: The Essence of Great Selling, my post from October 24th, 2024 if you want to learn more about Gitomer and Orlob). Of course, those aren’t the only two ways, but the work doesn’t end when you learn the different strategies, it continues as you work to understand who you are talking to so that you know when to leverage each.
We all know sales managers who just tell us that it’s about volume, it’s a numbers game. They are right to a certain extent, because if you talk to enough people, you are bound to click with some of them. But if you are only making deals with those you click with off the bat, you will not get more efficient; you will not get better unless you change something. We also all know managers who had some success as sellers, and then try to teach their team in every situation to do everything exactly the same way they did it. Problem is, it’s a different time, an evolving product, a different person, a different relationship, and perhaps most importantly, you are a different seller. So it might work here and there, but that’s not because that manager is improving you as a seller, the manager just figured out a formula that works for a certain type of situation.
So, you are left hoping that every buyer is the right personality type for the exact formula you were taught.
There is only one method that works with every type of buyer. You have to ask the right questions at the right times and know how to listen to the verbal answers, and observe the non-verbal cues of the buyer in a way that helps you understand where to take the conversation next.
You have to have enough business savvy to know how to solve for their answers to those questions, which will inherently encompass their problem. At least they will if you’ve asked the right question at the right time. If you can’t do that, you aren’t getting more efficient, you aren’t getting better, you are just making deals circumstantially, either due to outside circumstances, or due to the circumstances of the personality of the buyer you are selling to at the moment.
Now let’s talk about the situations. Even beyond the circumstances of the personalities that we, as sellers deal with, the circumstances of the world of selling are often at odds with the way in which we want to operate.
Most people are inclined to stick with the status quo, and a seller’s job is to drive change, most people want to take their time with big decisions, and a seller’s job is to drive urgency. Most people want to develop a routine and adhere to it, and a seller’s job is to disrupt. Sellers are constantly running up against social constructs that make sense for everyone else around them, but not for the sellers themselves.
This is why people inherently feel uncomfortable with sales, and when asked about being a sales professional, so many people say things like, “oh, I could never see myself doing that”.
So how should we think about dealing with people we don’t click with and situations that are not suited for our goals?
It is so important for sellers to find a balance between the incentives and drives that will make the sales organization and the seller successful, and the realities and human nature of the buyer. This means that sellers must always be operating to satisfy two different realities at any given time. That is stressful, but it is eminently doable.
Sellers must be patient and impatient all at once. This means that sellers must be quick to respond, quick to schedule, quick to plan, and quick to act. They cannot have any patients for procrastination and action on their part, but they have to display a reasonable amount of patience when it comes to client activity. For clients, the deal is not likely as high a priority as it is for the seller, but more importantly than that, the client has an entire buying organization that they have to work with to get things done, and any form of working with internal teams expends political capital. So, sellers cannot lose control and allow buyers to unnecessarily delay, but they must display patience and grace, and understand the buying organization and its potential delays.
In the same way, sellers control their actions, but not the ultimate results, so making cold calls and taking action is something that sellers have to be impatient with themselves about, but getting deals closed is something that sellers should be patient with themselves about because they don’t control the final outcome. To sum it up, sellers must be impatient when it comes to expectations of action, and patient when it comes to expectations of results.
Sellers must have a routine, and be flexible all at once. Strength in life is rarely about conviction, it is about setting boundaries, and a framework for yourself and following through with the right actions when conviction wanes. In other words, it’s easy to have convictions, and commitments wane over time, but it’s the framework, and the boundaries that you put in place that allow you to continue doing the right things and being successful. Similarly, with clients, they are not in your routine, so, while it is of maximal importance to have a routine in order to make sure you do the things you need to do, you also must be willing to be flexible to meet clients needs without losing focus on the things that need to be done. To sum it up, sellers must have a routine to fall back on over time, but flexibility in the moment.
How you balance competing interests is a major factor in how successful you will be as a seller. There are two ways to erode the possibility of making a deal. If it is clear that your interests are more important than the buyer’s, then buyers will not trust you and will not want to interact with you. On the other hand, If it is clear that the buyer’s interests are more important, buyer’s won’t respect you and they will become trained to devalue you and, by extension, your products. When there is an understanding that you, as a seller, have value, the buyer, as a person, has value, your products have value, and the buyer’s money has value, and all of those levels of value are similar, that is when deals get done.
Dan Greenberg · February 20, 2025 · 8 min read
We finished last weeks post talking about resilience and routine, so let’s put some more meat behind that conversation. I want to be clear here, picking up a phone book and dialing random people is not the answer. Obviously that is hyperbolic, but when I talk about cold outreach, I am not talking about the type of cold outreach that more traditional sales teaching was talking about in the 80s and 90s. This is because of all of the barriers that buyers have built up. We have mentioned in previous posts about how buyers are skeptical and jaded, and therefore cold outreach in the absence of research, targeted material and inbound signals is a tremendous waste of time and a resource suck.
The story of Chet Holmes is well known in the sales literature world, but it is basically the story of how Chet Holmes was hired by Charlie Munger (Warren Buffett’s business partner) to head up a large and struggling media sales organization. A couple of years into his time leading sales he was asked by Munger, “Are we lying, cheating, or stealing? I’ve never seen sales numbers this good”. The answer is that he was doing none of the above; he attributed his success to one important strategic decision. He had taken a list of 2,000 prospects, trimmed it to the 167 best potential clients and focused 100% of his team’s energy on those 167 clients.
This story is well known, and not new, but it teaches us a very important lesson, 10 well informed, targeted, tailored outreaches are better than 100 spray and pray outreaches. The time that you spend on cold outreach should not be spent on volume and tallying as many calls, emails, and messages as possible, it should be spent on research, tailoring of information, and crafting of messages that fit. The messages don’t have to be witty or perfect, they just need to speak to the person you are speaking to.
Many sellers are scared by this idea. They think to themselves; “what if I focus my list but accidentally leave off potential clients who really were interested and now will never buy from me?’ Sure, this is a slight risk but the real calculation is the value of all of the lost time that you will spend reaching out to clients that will be wasted because your messages are not targeted and don’t elicit a response. You are not a call center, you are an executive, and your job is to solve problems for specific clients that you select that are worthy of the time you will spend on them. That mindset is important when it comes to how you develop a prospecting plan.
Once you have wrapped your mind around that idea, then it is time to set a routine. Resilience is not some magical phenomenon or idea that is fundamentally built into the personality of a good seller by nature. Resilience is simply the setting of routines and the discipline to adhere to that routine without succumbing to the desire to avoid it. Routines need to be set because they contain the things that we don’t want to do. My favorite fortune cookie I ever opened was very simple; all it said was, “Winners do what losers don’t want to do”. This is very simple and true because there are very few competitive advantages in the world anymore. Given the flow of information and the sheer volume of people, there are just not a lot of completely unique skill sets or knowledge sets. But one area where you can differentiate is simply doing things that others don’t want to do. The good news is that being successful does not require sitting down and making 100 phone calls a day like a drone, as it used to.
The world has changed, we have more information and we can use that information to make our jobs more enjoyable and more fruitful. Information allows us to research, tools allow us to target and tailor, and platforms allow us to communicate in more effective ways than in the past. This means that instead of being a mindless drone and making the same phone call 100 times, you get to be an investigator for a while and figure out the best prospects. Then you get to be a researcher and learn about them and their companies. Then you get to be a marketer and tailor material that makes sense for each of them, and then you get to be a seller and send the messages and make the calls. Sure, you may not like every piece of the work, but it sure beats doing the same thing over and over again all day.
The key is to set time blocs and stick to them. Make sure that the time blocs make sense within the goals that you are trying to achieve, and that you are setting the right amount of time aside for the right activities, but treat those time blocs as close-to-sacred so that you are sure to do all of the activities that you can control and that lead to your success.
The last important thing to realize when thinking about prospecting is that inbound signals are very important. Depending on your organization, your marketing team may help with some of this work, but tailored messages to targeted individuals within researched organizations will elicit some responses. Sometimes these responses are direct message responses, sometimes they are visits to a website, or signups for a blog, or maybe even requests for information, but they are happening, and they are the strongest signal you have of potential opportunity. In outreach, familiarity is key, and the more times a client sees your name and your company name, the more familiar they become, so when you get a response, that is a client indicating to you that they are familiar with you, and that they have engaged their conscious brain in thinking about you and your company. There is no reason to spend a single minute with the best prospect in the world who has not yet indicated interest, if you could rather spend that minute with a qualified client who has sent some version of an inbound signal.
If your marketing team has set up systems for tracking inbound signals, that is good, but not enough. You should be doing the same thing with more targeted outreach that you are doing to your prospects. If you reach out to a client 5 or 6 times and don’t receive any inbound signals of their interest, add them to a group that you will put on hold and then reach out to again in 3 to 6 months. I see so many sellers try 5 times, decide a lead is a bad lead and then send it back to the marketing team. If you give a client a 3–5 month break, and then message them again, most will lose track of the circumstances of the original outreach. They won’t remember if they didn’t respond to you because you were annoying them, or because they weren’t interested, or because they liked your competitor better. They likely won’t remember any of that, but what will last is the familiarity and that will trigger them to pay just a bit more attention to your outreach.
The point is that the battle in outreach starts with visibility, moves to familiarity, and then to solution association. Your client needs to notice your outreach, then become familiar with you and your company, and then associate you and your company with the problem you solve. This can take months, and sometimes double digit outreach, which is why I started this section by talking about routines. You can’t sell anything to anyone until they are receptive to listening, so all of the commercial teaching, discovery, presenting, social proof, and everything else that we have talked about in past posts, and will continue to talk about, cannot start until you have crossed those three hurdles. The client has to notice your outreach. The client has to recognize your name and your company name. The client has to have a general idea of how you can help. The only way to make sure that is the case is to set a routine for yourself and to continue to take the actions necessary to drive those outcomes.
Dan Greenberg · February 6, 2025 · 6 min read
Sellers must spend more time selling. This is not really a skill or a behavior per se, it is more of a mindset or a discipline. Our modern work culture is full of distractions and secondary demands of our time, but we know what drives sales, and it is up to us, as sellers, to guard our time and make sure we are spending our time on the right activities.
A Salesforce study published in December of 2022, which studied 7,700 sellers from 38 countries published data that indicates that sellers, on average, spend only 28% of their time actually selling. This means that they spend 72% of their time doing other tasks.
It is unrealistic to expect that a seller would spend 100% of their time selling, as they do need to research prospects and clients, prepare presentations, and organize their sales activities. However, even when you pull those sales preparation activities out and add them to the sales side of the ledger, the report shows us that sellers are still spending over 44% of their time on administrative activities such as data input, and internal meetings.
Let’s keep in mind that this survey asks people to report on past activities, and studies have shown that humans are remarkably bad at doing this. However, the data is stark enough to give us a sense that there is something worth discussing here. But I would go a step further in assuming that not even the 28% of time reported by sellers as selling time is actual selling time. It is human nature to procrastinate that next cold call or cold email. Why? It will make someone uncomfortable. Or, the seller might get rejected. Or, it’s very monotonous work. Sellers don’t sell for many reasons; fear, boredom, desire to avoid rejection, desire to avoid failure, wanting to stay in their comfort zone, laziness. So, even the reported selling time is likely inflated.
It is incumbent upon sellers to develop a clear understanding of what their revenue generating activities are. Most likely the answer is something along the lines of; calls, emails, meetings, presentation building / meeting prep, research, and book organization. These activities, in aggregate, should take up at least 60% of the day, and in order to make this a reality, sellers must put time blocs on their calendar for these activities that are as immovable as client meetings. It is unreasonable to expect that sellers won’t have some downtime in their day, every worker does. It would also be unreasonable to expect that administrative tasks and side projects won’t come up. They will, and they aren’t necessarily bad. In addition, well-run internal meetings can be very effective, and trainings are a must.
But the just mentioned are not the activities that sellers end up flaking on, because they are the easy ones. They are the ones where you don’t have to exercise your mind and they are not mentally exhausting, they are the activities that don’t risk rejection and uncomfortability. So, when given a choice, as much as sellers complain about internal meetings, they often times secretly prefer them to the hard work. This is not a slight against sellers, it is just human nature. We work hard every day, it’s a grind. It is easy to let a little calling or emailing time slip through the cracks if you aren’t careful. But making sales requires the doing of selling activities, and the only way to ensure that they are done at a level that makes sense is to set time blocks and make them almost uninterruptible.
Everything above takes resilience. You will get rejected. You will send 100 well thought out emails one day, and get zero responses. I have touched on Daniel Pink’s ABCs of selling in past posts, The A is for Attunement and is focused on a sellers ability to understand the client. The C is for clarity and has to do with the sellers ability to communicate a message to the buyer. The one is most relevant to our conversation today is the B, for buoyancy. To Pink, buoyancy is the ability to stay afloat in a sea of rejection. I would take this a step further. It is not just the rejection that bogs down sellers, it is the consistent need to be “on”. Being “on” does not mean that you are somehow acting, or being someone who you are not. Being “on” simply means that your brain is engaged, and you are attentive, and perceptive. You are listening and thinking. You are not allowing yourself to switch to auto-pilot.
Human beings are inherently lazy. This is not a negative, it is an evolutionary necessity. We are lazy because it was incredibly important to our ancient, and not even so ancient ancestors, on limited food and resources, to be able to conserve energy, both physically and mentally, in order to be able to use that energy to escape or avoid any one of hundreds of potential life threatening circumstances, from lions, to enemy archers, to unexpected storms.
Avoiding auto-pilot, and being mentally engaged for long periods of time is extremely mentally exhausting. Remaining engaged in a sea of monotony, and amidst the constant drumbeat of rejection takes an incredible amount of resilience. But how do we achieve resilience? I can’t just say to myself, “Hey self, be resilient”, and then I will magically be resilient. Resilience is preparation. It is the discipline to set rules for yourself and then adhere to those rules no matter how distasteful the activities are at the moment. The rules should be attainable, and they should not drive you into the ground and overwork you, but they have to be likely to drive the outcomes you want to see, and you have to adhere to them. In a vacuum, or without routines and rules, resilience does not mean much because unless resilient thinking can be translated into effective activities, it will not change your outcomes.
Dan Greenberg · January 22, 2025 · 5 min read
Objections are an ever-present part of the sales process, and I have posted on the topic in the past (If you are interested in learning more about identifying objections, and handling them, please take a look at “Identifying Objections” from April 25th, 2024). In general, learning how to evaluate them, how to categorize them, how to respond to them, and how to move on from them can help minimize their impact.
What I want to focus on today is the discipline and ability to remain calm and not allow your own emotions to come into play in these types of situations. It can be easy to think about objections, in the classic sense, as specific pushback on the solutions, but, in reality, objections come in many forms, and can cause all sorts of reactions from sellers.
In addition to simple product or solution push back, objections can appear to be rude or negative comments made during presentations, they can look like jokes at the expense of the seller, they can seem like deliberate disregarding of information already come to agreement on, and they can be as simple as foot dragging at a crucial moment when the buyer already seemed fully committed.
What all of these situations and many others have in common, is that they can feel like doomsday scenarios to the seller. It can feel like all is lost. It can feel like the buyer is throwing you under the bus, and doesn’t care about you; it can feel like the buyer never had any intention of taking you seriously, and it can feel like you were so close to a deal, and now there is no chance it will ever happen.
I’m here to tell you that you are wrong. It’s not that you are wrong because none of the above are ever the case. Sometimes they are; sometimes the deal is just lost. It may be your fault and it may have been out of your control, but sometimes situations change and deals get lost. The reason you are wrong is because nothing the buyer has done is permanent, and the only thing you can do to make the situation better is to limit your reaction.
What I mean by this is that the buyer could be trying to win an internal battle and sees an opportunity to use you as a pawn. The buyer may just want to look good for a moment, and not even realize that they are coming off as rude. The buyer may have literally forgotten about something you have talked about 17 times because it is just not that high of a priority and they don’t understand it all that well. The buyer could simply be scared of being wrong which causes them to pause before making a final decision even if there is no good reason to do so.
The point is that when a buyer behaves out of the norm in one moment, it rarely means anything in terms of how they will behave going forward. Make the assumption that your buyer will revert back to the norm until they prove otherwise. If you make that assumption, it will be clear that reacting directly to their behavior is almost never necessary.
Once we are clear that no direct reaction is needed, the trick becomes controlling your emotions. When things like this happen and we are made to feel used, or belittled, it is easy to react incorrectly in the moment. Almost any reaction that you have to that kind of scenario will only serve to do two things. One; It will serve to create a divide between you and the buyer which will cause them to entrench on their side. Two; it will cause the negative situation to be more memorable which will make it harder to move past.
In a past post I talked about not allowing perfectionism to get in the way of starting to sell, and we have all heard the saying, “Perfectionism is the enemy of success”. It turns out, there is another reason to be out there with your client and have as many conversations as possible. The more you sell, the more you ask of people, the more you get rejected. And, the more you get rejection the easier it is to take it in stride.
Rejection is a fact of life, and it is easy to try to hide from it, and blame situations on other factors so that we don’t have to confront the reality of rejection. But, the more we embrace the fact that rejection happens in all kinds of scenarios, the easier it is to internalize the fact that it’s not necessarily our fault, and it is usually not about us. We are doing a hard job, in a hard environment, and rejection is a fact of life. Let it happen, embrace it, and move on from it, one rejection at a time. Because as hard as it is in the moment, it will build a layer of resistance for you that makes it easier to react the right way and control your emotions when there is an important deal on the line.
Rejections happen all the time, “I’m not interested”, “Call me in 6 months”, “We already work with someone on that”. Every time those little micro-rejections happen, handle them, and try to overcome them. Then embrace the fact that they happened. Then remind yourself that they have nothing whatsoever to do with you, and that they just aren’t that big of a deal. Then move on.
Dan Greenberg · January 10, 2025 · 5 min read
As you might imagine if you have read my past posts, I want to start the budget chapter by considering what the buyer is thinking about when a seller asks them for their budget. When most sellers ask for a budget, they ask it as one of a long string of questions that they had prepared to ask in discovery, and it is usually somewhat disjointed from the value conversation. This method of asking for a budget will cause most buyers to think something along the lines of the following; “this guy just wants to know how much money I have so he can start to think about how much of it he can get his hands on”. Sometimes this is a very conscious thought on the part of the buyer, but most of the time it is a bit more below the surface. Regardless, it affects the relationship, and definitely not in a positive way.
Worse however, than the effect on the relationship, and the interaction, is the action it causes the buyer to take. The buyer has no incentive at this point to share a helpful or conversationally progressive answer with the seller, because the buyer has framed the seller’s question for themself, in their own head, since the seller did not frame it for them. The frame in the buyer’s head is all about what the seller wants, so there is no incentive for the buyer to cooperate. Even more proactively, many buyers will start to think that if the seller is setting themselves up to talk about what they want, “maybe I should be doing the same thing”. So, they low-ball the answer. The first thing this does for the buyer is it allows them to position themselves for a potential price negotiation. The second thing it does for them, is it allows them to feel secure in their sense of control because they have just withheld information, and the third, and most important thing that this does for them is it allows them to show off or gain internal power by positioning themself as the hard ball player who is outsmarting the vendor.
Regardless of all the advantages that this has for the buyer, it hurts the conversation, and the likelihood of a positive outcome, and a deal, not to mention, the fact that a completed deal will likely be at a lower dollar value even if it gets done. For one thing, when this happens, the seller does not have an accurate number to work off of, and cannot put together appropriate packages, and offerings that make sense for the real budget. But of a much more consequential nature, once the buyer has taken a stand on budget, they have entrenched themselves in that assertion, at least to some degree. For a buyer, finding more budget when you have not previously stated a limit makes you a hero, but finding more budget when you have already stated a limit makes you a flip flopper, and even worse, a softy or a bad negotiator. If a buyer states a max budget and then goes back on that limit they have forfeited all of the above mentioned security, sense of control, and enhanced social standing within the buying organization that they earned by setting that limit in the first place.
For all of the above reasons, it is so important to avoid a situation in which you ask the buyer for a budget with lack of context, and lack of conversational framing. If you have been reading my past posts, I may sound like a broken record by saying this, but what needs to be done is that the seller needs to reframe the ‘budget ask’ by getting back to the problem and the ideal outcome for the buyer. The client must be thinking about the problem and the world they want to get to before they think about the budget; that context is key in order to get a real and honest answer that helps move the conversation along.
In fact, you don’t even really want to ask the budget question in so many words. Your lead in to the budget conversation should sound more like the following: “Given the conversation we just had, what is the monetary value of that ideal outcome that you are hoping to get to in the relatively near future? Can you put a price tag on it and does it even make sense for your business to think about solving it with a third party solution?” What you have done here is asked the buyer to wade into the budget conversation in the context of their problem and their ideal solution, and not in a vacuum. More importantly, you have done your best to associate them spending money with the outcome itself, not with your “greedy” revenue goals. Of course people are not stupid, and you are not pulling a fast one on the buyer. They still know they are talking to a person who wants something, but context and association matter, and can elicit big differences in responses.
If you don’t ask the right set of questions, and you are not able to get an understanding of the client’s budget, as well as other potential budgets that can be drawn from, and all the dependencies, you are not doing your job. However, if you have to ask the question directly, you also did not do your job. It is incumbent upon a seller to facilitate conversations that start with problems, advance to desired outcomes, and contextually value the two so that an understanding of the negative value of the problem, and the positive value of the desired solution are understood. Then, within that context, the available budget can be compared to the price tag.
Dan Greenberg · December 20, 2024 · 6 min read
We have spent the past three posts talking about discovery, and I would like to continue the series as it is such a vast topic that influences so much of the sales cycle.
Discovery is not a discrete portion of the sales process but rather a consistent ingredient of every interaction from early introductions to post close. For this reason, discovery has to be connected to the insights that you offer your client, and the value that they will get out of your solutions, and out of a relationship with you and your company. One of the key things to think about when it comes to insights and value add is that the focus of these conversations needs to remain far away from solutions and products.
The focus should be on the buyer’s current situation, the status quo, the buyer’s desired outcomes, and the change to the status quo. It should have nothing to do with solutions and how your product will get them where they want to go. In discovery, it is the salesperson’s job to get the client to paint a picture, in their own mind, of where they want to be. In order to complete this task, we want the buyer to describe their situation in their own terms, describe how that situation affects them, describe what that means for the business, and describe what the ideal outcome looks like and how much that is worth to them. Notice that nowhere in the discovery description did we discuss how to solve the problem, and the details of the journey, we just helped the buyer describe the journey. The how-to will come later.
The reason the how-to comes later is because if we try to understand the situation, and the problem, and present the solution all at once, we run into a credibility problem. As you learn about a complicated problem, moving straight into a solution explanation that happens to solve all the points of the complicated problem, just does not seem probable. Either your solution is a one size fits all, which is perceived as less desirable to buyers, or it is customizable to their exact needs, which would mean you would have to take time to put together a solution that works for what they told you. Additionally, as we have discussed in other posts, as soon as you move to a discussion that includes the solution, you move the buyer from a collaborative position where they are working with you to build a vision of the desired outcome, to an adversarial position where they are sitting in judgment of the solutions. This is why it is so important to spend this learning and insight sharing time talking about the situations, and the problems, and the value and the outcomes, but leaving the solutions off the table.
So, all of this leaves the question; how do we get from situation and problem, to desired outcome, without traveling through the solution that bridges the gap? And, how do we do it in a collaborative way where we are positioning the client to drive the conversation?
It is important to be aware of the psychological, and emotional burden that you are placing on the client throughout the process. Look for signs of stress, annoyance, and mental laziness. These all indicate that the buyer is not in the mood to think deeply about problems, and / or not in the mood to share the answers with you. Seeing signs like this should indicate to you that you need to introduce a change of pace to the meeting. Whether it is moving back to easy situational questions, or presenting an insight, or even a teaser about your products that they had been asking to see, or it could even mean dropping the business conversation completely, and trying to move to a lighter topic.
Being aware of the buyer’s mental state is incredibly important and that is one of the reasons that the next step here is about outcomes. As the buyer starts to think about the problems caused by the situation, you can start to invite them to opine on their theories about what it does to the business and how the bottom line of their business unit and the overall company are affected by those problems. From there, it is not much of a leap to start to discuss desired outcomes. The buyer is encouraged to envision a world in which their problems are fixed, and where they don’t have to deal with the problems of the status quo anymore or the business implications of those problems. Since you have already eased them into the discussion, they have been primed to move into a state of mind that is more conducive to answering questions like these, and when done right, their comfort level with the asker of the questions allows them to move into more psychologically and emotionally burdensome answers without developing a strong negative association with the asker. In addition, the nature of these questions, allowing them to think about desired outcomes is inherently hopeful, as opposed to questions more focused on problems.
Discovery cannot be completely about pain and problems. If it is, your client will always associate you with negative feelings, and eventually they will find a reason to stop talking to you. The needs/ payoff questions that we discussed in my post on SPIN Selling on November 21st are designed to understand value, and the lens through which that works is a lens where the buyer is encouraged to envision a world in which their problems are fixed, and where they don’t have to deal with the problems of the status quo anymore. This line of questioning builds directly off the implication questions, and asks the buyer to envision the desired outcome and to start placing a value on it. If your questions can push the buyer to talk about this desired outcome state, you can then start to establish the value of that state, and then, conversely, the negative value associated with the status quo state.
Remember that discovery is not about selling. It is not about solving problems, and it is certainly not about your solutions. Your first job in discovery is to earn enough license and allowance from the client that they are not constantly expecting you to put on a demo like every other seller. Your goal is to derail their idea of a pitch, and turn it into your mutual idea of a business conversation. Sometimes that means giving them a little bit of what they want, or a teaser, but from there, it is important to move to conversation and collaboration. After you have accomplished earning that allowance, the next big job in discovery is to position the questions so that the buyer spends their time comparing the problematic and boring status quo with an exciting, and hopeful desired outcome. Again, none of this has anything to do with solutions, it has to do with their status quo, and their vision for the future.
Dan Greenberg · December 6, 2024 · 6 min read
I have spent the past couple of posts talking about discovery, but we have not talked much about what makes a good discovery question, and why.
Last post we discussed Neil Rackham’s SPIN Selling and the four questions that you can use to progress through a discovery cycle. The post before that we discussed the overall nature of discovery questions, and how to think about our preparation. Now, I want to spend a bit more time talking about the mechanics of the preparation and the questions themselves. It is impossible to keep all of the information and questions in your head and pull off a flawless discovery session without preparation. It is very important to put down on paper lists of questions that you want to ask a client so that you can internalize where you want to get to in your discovery focused conversations.
However, remember two things when doing this type of prep. The first is that you need a lot of situation and problem questions to set the stage and then fewer implication and needs / payoff questions because as you move towards the implication and value conversation it needs to turn into just that, a conversation, not a list of questions. The second thing to remember is that your list of questions is not sacred. The point is to prompt the buyer to lead you somewhere. Follow up and genuine curiosity are much more important than your questions, so long as you can keep the guardrails on and remain commercially relevant.
Let’s think about why we ask certain questions and what we are trying to get out of them. Let’s inspect some common questions and understand what is good and what is bad about them, and what that means in terms of your execution and your follow up after you ask them:
“What is happening in your business right now that is causing (x issue) to be a priority?”
Half of your job as a seller is to figure out why most of the people out there hang up on you and get angry when you keep bothering them, and don’t have the time for you, but this person you are sitting across the table from is actually taking time out of their busy life to talk to you. Time is valuable to decision makers, and even if it is not, mental energy is valuable to humans, so if someone is taking time and energy to talk to you, there is a reason. Why now? Why not later? What is being deprioritized in order to focus on this? It is your job to figure out that reason. The key with a question like this is follow up. This question by itself is not enough because most of the time you won’t get a full answer, but more importantly, the answer only tells you why they are exploring, and exploration is far from need, so while this is a good question, good follow up is key.
“What metric is suffering most as a result of the problem you are describing?”
Understanding why a decision maker is exploring a solution only means something if you can understand how they measure that problem, how important the problem is, and if solving it would likely cause other problems that are bigger, or seemingly bigger than the original problem. Metrics are a good place to start. If you understand the metric that the business wants to improve, how visible that metric is, how much people internally care about it, and what else it affects, you can start to make progress in having the right conversations. However, this question is not enough. It takes smart and persistent follow up to move from the metric that is suffering to the relevance, the visibility, the relative value, and the secondary effects.
“Tell me about your biggest challenges when it comes to (x issue)”?
This is a very open ended question and it allows the buyer to answer in a pretty unrestricted way, but at the same time it limits the buyer to the issue at hand. If your questions are too broad, you may not get relevant answers, or your buyer may feel overwhelmed by the possibilities and respond in an unhelpful way. Be aware of the level of breadth in your questions. It is important to open up the scope of your conversation to all potential answers that are relevant without being so broad that you end up at an irrelevant place. Again, with questions like this, follow up is key; once you understand the challenge, you have to go deeper. It is important to probe regarding the challenge and its details and its effects on the person you are talking to and their team.
“How is this decision going to be made? Who will be involved? And what does the process look like?”
It is always important to understand the process that the buyer has in place, especially in longer sales cycle deals. It is also useful to ask multiple people this question, and to ask them if they feel comfortable with the conversation and are able to help you navigate the internal process. Human nature makes most people naturally want to be helpful, and as soon as an individual on the buying side verbalizes a commitment to help you navigate the process, they become mentally invested in helping you. Make sure not to get stuck on the first level. If you ask someone about the internal process and they give you an answer, then the next thing you should say is, “and then what?”, and when you get an answer to that, you should say, “and then what”. This is a powerful way to influence your stakeholders to think about what they really need to happen to get a deal across the table. This will start them down the path of investing that mental energy into the deal itself.
The basic takeaway from all of the questions above is that you need the answers and they need to be asked, but they are generic. So it is important to inspect them and understand the positives and negatives so that you can do two important things:
Discovery preparation is incredibly important, but it is not enough to just write down some questions. The key is to inspect what you really need to get out of those questions and think about how you will customize and position them in order to earn credibility, and how you will follow them up in order to learn the information you need to learn.
Dan Greenberg · November 22, 2024 · 7 min read
In this post I am going to spend more time talking about discovery. I rarely stay on the same topic for two posts in a row, but there is so much to talk about when it comes to discovery. Discovery is what makes or breaks your ability as a seller to be influential. It is not a stage in the sales process, it is an ever present, and consistently necessary component of every conversation from the first time you interact with the client until the ink hits the paper.
There are certainly different possible approaches to building out a discovery strategy that can be effective but I wanted to call out Neil Rackham’s approach because it conforms well with many of the concepts that I have written about, and because it is a well formulated strategy that sets a seller up nicely for execution. I highly recommend the book.
In his book SPIN Selling, Rackham lays out four different types of categories that any discovery question would fall into. I am going to go through the categories as Rackham lays out, and give a quick overview of the book, but then I want to spend a bit of time dissecting each category and expounding on them so that we can get a better understanding of how they relate back to the conversations and your ability, as a seller, to move conversations up the value chain.
The first category is situation questions. Situation questions establish the current situation that your buyer finds themself in, they are answered by factual statements, and establish the starting point for the conversation.
The next category is problem questions. Problem questions allow for the buyer to answer with statements of fact about the problem that is being caused by the current situation.
The next category is implication questions: Implication questions move deeper into the buyer’s mind and are answered by opinions, assumptions and predictions. They ask the buyer to understand the problem and explain what it implied for the business.
The last category is needs / payoff questions: Needs / payoff questions ascertain value. They are answered by prioritizations, and assertions of relevance that establish the value of a potential outcome, and the cost of the absence of that outcome.
There are a few reasons why this framework makes sense. For starters, it allows the seller to ease into questioning. Asking a client about current situations allows the buyer to answer somewhat softball questions. Facts are easier for people to come up with than opinions, and analysis. They take less mental energy and they feel less intrusive, so starting with fact based situational questions does not carry much mental or emotional burden. Of course, it is important to make sure that the questions aren’t simple enough answers that you could have and should have researched them before getting to the meeting.
As you ask a number of situational questions, and the buyer gets a bit more conversationally comfortable, moving to problem questions, which normally carries a heavier emotional burden becomes more acceptable and easier for the buyer to call to mind as they have already been prompted to think more seriously about the situation.
Starting with a number of situation questions, then progressing to a few problem questions, then narrowing that down to a single implication question followed by a single needs / payoff question is a powerful formula for getting to the root of a problem, as well as the desired solution. Keep in mind however, that you will need to repeat that process many times with many people in order to get a full understanding of all of the buying organization’s problems and how they are prioritized one against another.
In past posts, I’ve commented on my displeasure with the common saying that “bad sellers sell products, and good sellers sell solutions”. My issue is not that it is incorrect, but that it falls far short of being explanatory enough to be informative. In order to understand the difference between good and bad sellers, we need to shift the scale and go much farther. The better a seller is, the farther up the value spectrum they live. Moving from selling products to solutions is good, but selling outcomes is better, and selling on value is best. More importantly, we can use discovery preparations, the discovery process, and Rackham’s methodology as a tool to move in the right direction along that spectrum.
Dan Greenberg · November 8, 2024 · 10 min read
Basic curiosity is one of the best tools for improving your outcomes in sales. If you want to be great at sales, nurture your curiosity. Like any other muscle, it needs work. Read, watch, listen, observe the world, and think about how one occurrence or situation has implications for another. Although every situation is different, people, on the whole, generally respond to incentives in similar ways, so there is often insight that can be gained from observation of one situation and applied to another. That framework combined with genuine curiosity about the business results and outcomes of a buyer’s business can lead to very insightful conversations which provide a great deal of information to you, the seller.
It is much more effective to be a great business person who happens to be good at sales rather than trying to become a great salesperson in a vacuum. This is because being a great business person allows you to connect with a real decision maker on issues that make a difference to their business. This ability will allow you to add insight, and value, or at the very least commiserate with that buyer in a way that will open them up to a comfort level that will cause them to share vital information. It will also imbue you with the credibility necessary to allow you to both, ask additional questions, and be persuasive as the process progresses.
I have written in the past about earning the right to ask questions, and adding value to the conversation. Think about this like greasing the wheels. If you were to ask a potential future partner of yours, on a first date, how many kids they want and what they plan to name them, and then go on to tell them that you love those names and would totally want to use them on the kids you have together, and oh, by the way, you just happen to want the same amount of kids as they do, and maybe we should get started now…. Anyway, you get the idea, that is coming on pretty strong, and there is a pretty good chance the person on the other side of the table is going to call you out on it, or more likely, and even worse, finish the interaction awkwardly, and then ghost you.
Sellers do the equivalent of this all the time. They will ask obvious questions like, “what is causing the biggest problem for your business right now”, or, “what keeps you up at night that you need solved right now?” While there is nothing inherently wrong with those questions, they will ask those questions on the first interaction without earning any right to go that deep, and without even spending the time getting the buyer more comfortable socially. They will then proceed to tell them how magically, their solution happens to perfectly solve all of the problems that the buyer just mentioned. Not only is this not believable to the buyer, it is disingenuous, and irritating, and it causes the buyer to feel underestimated. In their head, they are likely thinking something like, “This guy thinks that I have this big problem which I haven’t even fully explained to him, and there is a perfect solution out there, and yet, I somehow have never thought about using it?” Basically, this kind of rapid discovery is irritating, lacks credibility, and essentially calls the buyer an idiot. On that note, let’s take a look at a few Discovery Don’ts.
In addition to considering these Don’ts I also wanted to write a bit more proactively and positively about some Dos. It is important to be prepared for discovery and think about the types of things you want to learn about. Here are some ways to think about that preparation.
It is vital to be thoughtful about discovery. If your questions are generic, invasive, robotic, or overly simple, you are sending a signal to the client that the conversation cannot add value to their business. And, if you can’t add value to their business, they will have no reason to open up to you and have real conversations.
Dan Greenberg · October 23, 2024 · 8 min read
Wouldn’t it be great if it were simple? Just read this article and you are all set. You will understand the essence, and you will be a great seller. But, as we all know, there is nothing about learning to sell that is tied up in a neat little bow of catharsis. The secret is that there is no secret.
I read a lot from Chris Orlob, former sales leader at Gong, and successful sales trainer. He, and many other great sellers and experts will talk to you about finding the buyer’s pain, and consistently returning to that pain so that your solution has context and meaning for them.
Here is Orlob talking about finding and framing around the buyer’s pain, “Here’s a mistake almost all salespeople make on sales demos: Forgetting to frame and reframe the pain each feature solves. Not just at the beginning of the call…”
I also read a lot by Jeffrey Gitomer, prolific author and self proclaimed King of Sales, also mentioned above. He and a number of other excellent sellers and experts will talk about relationship building and keeping interactions positive. They focus on keeping the buyer in the right mindset and staying away from conversations about pain.
Here is Gitomer on staying away from “pain” conversations, “If you’ve taken any training in sales in the last 50 years, you’ve probably heard this phrase: “Find your customer’s pain.” What keeps them up at night? What’s going wrong with their business? What do they hate about their competitors? Personally, I cannot stand this approach to sales. It’s a tactic from the old world of business. And it’s about as subtle and obvious as a freight train…”
You could be forgiven for getting a bit of whiplash reading these one after the other. Orlob essentially says that if you don’t consistently reference the buyer’s pain, there will be no context for your solution and the buyer won’t make the connection so you won’t make a deal, and he has been incredibly successful with his approach. Gitomer, on the other hand, is saying that if you bring up pain, you will put the buyer in the wrong mindset and you will sour the interaction causing the buyer to become closed off and you won’t get a deal. He has also been very successful with his approach.
So, which is it? Who is right? I am a big fan of both Orlob and Gitomer, so would you be surprised to hear me tell you that both are right? It’s true, I mean, that’s not an ideal answer for you because it means that there is no easy answer. It means that it’s going to take work and effort for you to improve and incorporate these philosophies into your selling.
Of course, what I am saying here is that it is situational. Gitomer is right in many situations where the relationship is newer and the client may not be fully bought into your level of expertise or the relationship with you. As Gitomer goes on to explain, if you haven’t built proper rapport with a client, bringing up pain points will make the client uncomfortable and will cause them to associate you with that negative feeling making it harder for you to develop a good relationship. The client will become defensive and less willing to engage in real conversation. Orlob, on the other hand, is right in situations where the value proposition is at the core of the conversation, but only in situations where you, as a seller, have already sold yourself, and your value as a consultative partner. If the client does respect and trust you, the seller, independent from what you are selling, then talking about features and products without connecting to the pain will be a disconnect for the client. As Orlob goes on to explain, when you talk about features without framing it in the context of the problem it sounds like a feature dump. You will have a client who trusts you to be concerned about their business, and they will see you as talking about the things you care about instead of the things they care about.
So where does this leave us? If we have two experts who are both right, who do you listen to? That is part of what this blog is here to work through. The fact that sales deals with living, breathing, deciding creatures is what makes it so hard. There are often answers that are right in some cases and will kill a deal in other cases. The only thing that allows you to know the right course of action is your attention and perceptiveness. You have to be attuned enough to know which situation you are in.
Let’s look at this from a slightly different angle to help make it make sense. Marketers can always talk about the pain because the reader of a marketing piece is not vulnerable in front of another person. Marketers are talking through a screen and not face to face. This means that the reader of the material won’t experience nearly as much discomfort because they are not in a social interaction where they feel a need to justify their past decisions and position themselves as strong and capable. As sellers, we don’t have the screen to divide us from the client. Sellers have to be able to pick up on subtle cues that tell us if the buyer is feeling vulnerable, or uncomfortable, or if they are feeling trusting, and like they want to learn.
This is hard to do because humans have been learning to lie with their faces for their entire lives. In Joe Navarro’s excellent book, “What EveryBODY Is Saying” he discusses, at length, the amount of practice we, as human beings, have had lying through use of our facial expressions. We have been taught to betray our actual feelings using socially acceptable facial signals since we were young. Therefore, it is very hard to pick up social cues from people’s faces, because we have been training ourselves to present the message we want to present for our whole lives and not present what we are really feeling. There are many other cues that we can start to learn to pick up on, but they are more subtle, and it is harder to do. Where sellers have a hard task is that we have to deal with the person, and all the politics, and vulnerability and personality that entails. We have to know when we have permission to pry, and to get to the point, and to really be direct about the pain and the solution and when we don’t have that permission.
Pain is a necessary part of any sales conversation because it connects the thing that a seller is trying to sell back to the thing that the buyer wants to overcome. Sure, that could be a pain point, or an opportunity, but either way, the buyer is missing out on something they want. The seller’s job is to emotionally connect the buyer to that desired state, whether it be the resolution of a pain or the pain or not being able to reach a potential opportunity. Closing a deal is, in large part, a function of making that emotional connection happen, which starts with connecting the solution to the pain, and helping the client visualize the desired outcome.
On the other hand, if the conversation revolves around pain the client’s emotional signals will be negative, and their subconscious mind will help their conscious mind find a reason to avoid you so that they can avoid the negative emotion. The hopefulness of the buyer’s desired outcome has to override the pain of the problem in order for them to want to work with you to get there.
Sure, as mentioned above, the timing matters. While building a relationship, positivity is important, and while closing a deal, connecting the solution to the pain is important. However, this article is much more about reading your client than anything else. Clients who are not emotionally engaged need to be reminded of pain, and clients who are focused on the negative need to be reminded of the hope that comes along with their desired and achievable solutions. Where your client lies on that spectrum; figuring that out is your most important job as a seller.
Dan Greenberg · October 14, 2024 · 6 min read
We have all sat through bad meetings. Many of us have also been meeting planners and have spent time trying to find and mold content to fill up a meeting. There are important and foundational activities that sales leaders can use meeting time for that will help drive success and bring a team together. Meetings are important and useful when used correctly.
There are four foundational tools that can be used as the building blocks for organizational or team strategy, and they can be built by leaders with their teams in order to help build consensus on strategy, and learn the market together as a group. Working with your team during team meetings to build these foundations will be a positive use of time and a good experience for your team. The four foundational building blocks are 1) a SWOT based on perception; 2) a Brand Worksheet; 3) A prioritization, and focus hierarchy; 4) and a Business Playbook. Let’s talk about each of them in more detail.
Not having a playbook places the onus on the individual sellers and front line managers to be able to refine messaging and, articulate internal needs, and define rules of engagement and prioritization. Although sellers and managers should be able to think through much of this, it is important to work through these strategies as a group and unify the approach. If you don’t you will be watching a bunch of individuals operate in isolation as opposed to leading a unified team.
Dan Greenberg · September 27, 2024 · 7 min read
I’d like to start with an almost certainly apocryphal story about one of the first people to invent a pocket sized electronic calculator, and his visit to an accounting convention. The truth of the existence of the story is much less important than the takeaway from it. As the story goes, the inventor of this revolutionary piece of equipment circled the floors of the convention wowing his audience. The accountants were in awe of the simplicity and functionality of the device. The speed with which they could do calculations, and the portability of the device made it a no brainer. The only issue for the inventor of the device that day was that he did not make a single sale.
You see, each conversation went extremely well until the point where he told the accountant the price. Sure, the calculator was a spectacular piece of technology, and made them better at their jobs, and more efficient. But, the question was, how much better? and, how much more efficient? And, how much, in dollars, was that improvement worth to them? The inventor had answered all of their questions about the product, and the use cases, and even the vision of what their world would be like when using the tool, but he didn’t answer that last and most important question. How much was that new reality worth to them, in terms of real dollars, right now.
There are four basic ways to position value as far as your solution is concerned. It either drives revenue, reduces costs, improves efficiency, or mitigates risk. There can be overlap. Solutions often reduce costs, and mitigate risk. Solutions can often maximize efficiency, which in turn, reduces costs or drives more revenue. But the point is that you have to be sure which one resonates most with each person you are talking to, and then you have to figure out how to quantify that value, and then pit it against the negative value associated with not making a change. The inventor of the calculator never did that with his accountants and therefore the first time they thought about the price of the solution was in a vacuum. An expensive product is only expensive relative to something. If I tell you that you need to give me $1 million and in exchange, I’ll give you $2 million tomorrow, I may sound like the infamous Nigerian Prince, but assuming you believe me, that $1 million cost is not expensive. In fact, it’s the opposite. But if you hear that something costs $1 million in a vacuum, and you are not thinking about it in context of the benefits and costs associated with the status quo, then $1 million is expensive, and that is the first and only thing you will think about.
The other thing that sellers need to be very aware of, when it comes to value is understanding if they are selling something that is revolutionary or simply incrementally better. Selling a revolutionary solution means you better convince the buyer that they have been doing things incorrectly for a long time. You need to provide insights that show the costs of the status quo, and you have to prove to the buyer that the value of doing things differently far outweighs the risks of the change and the costs of the status quo. If you can do this, you are likely to have little direct competition, but that is not something that is easy to convince a buyer of. Incremental sales mean you better convince the customer that you are the best, that you are an exact fit for the category they already have, and that the switching costs are worth the incremental improvement. This means that the client has already identified the problem and taken steps to address it. They may even already have a vendor. The value equation here is much different because instead of pushing back against the status quo and alleviating concerns of risk, you are positioning your value directly against the value of competitors. They may cost more, or produce less efficient results, or solve fewer problems, thus indirectly leading to higher costs, or have any one of a number of other potential deficiencies that you can speak to, but the point is that the value conversation is much different. The value that you provided does not have to be established as being needed, but it does have to be proven. In these situations, you don’t have the hurdle of convincing the buyer that there is a better way, you just have to prove you are the best among stiff competition.
Your clients will not normally take the time to build a scenario that shows the status quo or the competitor and all the costs associated with that decision versus the benefits, and then compare it to you. procurement may do it at a very cursory level, but it will be highly focused on costs and resource allocation, with a tacit nod to benefits. They will also almost certainly not discuss it or share it with stakeholders. Stakeholders most likely will not do this because they feel like they have a good understanding of the issues, and can reason it out without spending the time doing this. Even if they do it, it will likely be to check a box, and may not factor in all of the components that are important.
As you move towards the end of a sales cycle, if you have provided insights, and not acted as a one dimensional cheerleader for your products, you will likely have earned the social and relationship license to help the client in their calculations. You are allowed to do this because you are a salesperson, trying to make a deal, and everyone knows that, and we are not trying to hide from it, so it is expected, but at the same time, you have not spent the entire sales process blindly advocating for your products without taking into account your client’s other constraints and business realities.
In this moment, you have moved to a point in the process where you can transition from someone who was helping them bridge the gap from problem to outcome, to someone who is now helping them bridge the gap from decision to execution. If they are leaning towards buying they will want that help, and you giving them a story to tell internally to procurement, accounting, and other stakeholders is helpful.
When you help your client build a model that assesses costs vs. benefits, you can do a side-by-side with competitors, or simply show your value-add relative to the status quo. This is a decision for you to make in the moment, and depends on a number of factors. Don’t give a competitor legitimacy by including them, if you think you are the favorite. At the same time, if you think you have a definitive way of out positioning your competitor, and you think it is a tight race, you may want to include them. A lot of the decision making process on this will come down to where in the pecking order you feel you are, and if you are pitching incremental improvement or revolutionary change.
Once you have made your decision, factor in all of the costs of selecting your solution for the client. If you just factor in the cost of the solution, they will take you much less seriously, because you didn’t bother to factor in resource costs, and other process costs required for implementation and integration of your solution. Add those in and ask if you are missing anything. This also gives you license to add benefits that are tangential to a decision to go with your solution. Be realistic, and help them understand the real value tradeoff. This is important because they will likely not have put all of this together in their head yet, even though they conceptually understand it all. But it is also important because you are giving them an anchor point from which to tell their story internally.
Dan Greenberg · September 11, 2024 · 7 min read
“You have to sell the bucket before you fill the bucket” — Lou Paskalis, former SVP Marketing at Bank of America — He was referring to the idea that you have to sell the need for something before you sell the solution to the need. The idea is a simple one, but it reminds us that no matter how good we are at talking about solutions, the solution to a client problem is irrelevant unless the client has already come to terms with the idea that they have a problem, that the problem has a solution, and the the solution is potentially valuable enough to evaluate.
Even if a client does recognize the above, the mindset of the client is very important. The framing of the conversation must focus on the problem and the desired outcome, otherwise the debate becomes about specifics of the solution, not the need for a solution. If you are talking about solutions without framing them in the context of the problem and outcome, your buyer will focus on what’s wrong with your solutions, rather than the need for a solution.
Not only does solution selling in the absence of problems and desired outcomes focus the buyer on the wrong things, it also disengages the buyer from any form of collaboration with you, the seller. It disempowers them and leaves them two choices because the assumption is that there is nothing to figure out. A solution seller has already decided on the problem and the outcome for the buyer and is just trying to convince them of the superior qualities of their solution. So buyers are left with two choices; they can disengage completely, since the seller has already figured everything out, or they can engage in a power struggle with the seller, where they attempt to frame themselves as the judge and the seller as a vendor, like all the others. That is a power struggle that a seller is not likely to win.
It is very important to think about how straight line solution selling disempowers and disengages buyers, so that we, as sellers, can start to think about how we can empower buyers and collaboration, while keeping control. Understanding problems and outcomes and deemphasizing solutions goes a long way towards accomplishing this goal.
A focus on problems and desired outcomes helps to empower your clients and their desire to collaborate with you. Just as importantly, it helps tremendously when it comes to driving urgency. A focus on your solutions means that clients are not thinking about their business critically which means that there is no client problem linked to the conversation that would be driving any need to change at any particular time. A focus on problems and desired outcomes, however, illustrates for the buyer that the current problems are costing them money, which means that the longer they don’t make a change the more money they are losing.
In order to use the “problem” / “outcome” rubric to drive urgency, one of the most important behaviors to master is that of quantifying pain. If you can’t quantify pain, good luck securing budget and good luck driving urgency. Quantifying pain won’t close deals on its own, but it allows you to construct a picture of the loss that the client is experiencing so that you can build a real “loss aversion” story, based on problems and outcomes, as opposed to a “benefit” story, based on solutions. Think about asking questions like: “What metric is suffering most because of this challenge?”, or “How much is this lack of efficiency costing your business per year?”
These types of questions help get you on the right track in terms of quantifying pain.
There is a tricky line to walk here, because if you only remind buyers of their problems, and do nothing else, they will start to develop negative sentiment around their interactions with you, which will lead to a subconscious bias that will cause them to want to spend less time with you. So, you must balance out all of the “problem” talk with something that is more positive. And what is that positive balance? It is the “desired outcome”. The buyer gets to talk about exactly what they want and exactly how the future state should look having nothing whatsoever to do with your solutions, or anyone else’s, for that matter.
Building urgency and quantifying pain takes discipline. Most people answer questions about their problems with answers that illustrate a solution that they want, and although it is good to have your client talk about their desired solutions, be sure that solutions and outcomes are not conflated. Push them to talk about their desired end state, not the quick fix solutions for their problems. More importantly, push them to talk about the problem and the root causes of the problem rather than just the solution they want.
Product people that I have worked with in my career tend to be very well disciplined in this conversational tactic, and one person in particular comes to mind for me, so a special shout out to Julie Pifer, now Sr. product lead at Strategus. When internal stakeholders ask product people to prioritize a product or to build something, the reaction is often, “Don’t tell me what you want, tell me the problem you are trying to solve”. Sellers can learn a lesson from this conversational strategy and use it in sales interactions. Make sure that you don’t let the buyer off the hook. It is important for them to talk about the problem, the root causes of the problem, and the quantitative value of the problem for their business. You won’t understand the problem unless they explain it to you, you won’t be able to talk about solutions until you have agreed on the root cause of the problem, and you won’t be able to drive urgency until the problem is quantified.
If you lose discipline and allow the buyer to get away with not answering your questions, you will lose the ability to keep control, and you will lose the ability to empower your buyer and work collaboratively with them. Of course, you will lose the ability to drive urgency, but that will become a secondary problem because if you lose the ability to influence the deal itself, the urgency becomes a moot point.
“Selling the bucket” means framing the solution in the context of the problem and the desired outcome, and constantly reframing so that the client is in the right mindset. What we are talking about here is the blueprint for that strategy. Encourage the client to talk about their problem, the root cause of their problem, and to quantify it. Then summarize and discuss the impact of the problem and the desired outcome. Be targeted in your questions so that the client does not feel like they are doing all the conversation work, but don’t let them off the hook if they try to remain in the shallow end and only discuss solutions.
The only caveat is, remember to balance. You don’t want to be the person that constantly reminds the buyer of all of their problems and how terrible their business is. If you are always, and only, that person, they will associate you with pain, and start to create justifications in their mind for why it does not make sense to interact with you. Remember the dichotomy that we have been discussing. Make sure to balance conversations about problems, with hopeful conversations about desired outcomes.
Without being framed around problems, your solutions will be evaluated in a vacuum that is not beneficial to you, or your clients. However, too much “problem” talk is detrimental to the relationship. It must be balanced with discussions of desired outcomes, and a future state that is emotionally, and intellectually hopeful, and demonstrably better than the status quo.
Dan Greenberg · August 21, 2024 · 7 min read
In previous posts I have written about what I call “The Switch Points”. These are the points in time in sales interactions where we switch from a more social interaction to a more business focused one, or from introductions and greetings to the more formal part of the meeting, or really any switch from less structure to more structure. What happens during The Switch Points is that the meeting resets to a certain extent, and no matter how well the seller has done retaining control up until that point, the buyer is afforded an opportunity to reclaim control. This is because, when the meeting shifts to more structure or formality, the buyer can reframe the situation with the seller presenting solutions as a vendor, like all other vendors, and reframe themself as the all-knowing judge who gets to evaluate that presentation.
Switch Points will happen in meetings, no matter what lengths we go to in an attempt to avoid them. This does not mean they will happen in every meeting, but they will happen; so it is a good idea to prepare to deal with them. However, what I want to focus on in this post is deciding what type of meeting your interaction should be, given the understanding that switching presents challenges.
One of the ways to avoid the perils of a Switch Point is simply to not have one. If a meeting is conversational, it can remain conversational throughout, and if a meeting is a presentation, it can start as a presentation from the beginning. This won’t always be the case, sometimes you will decide strategically that a meeting should have both components, but oftentimes there is no need for a meeting to contain both components, especially in more strategic longer deal cycle sales processes. More often, transactional, high volume selling will require both components in single meetings due to the shorter sales cycle and need to accomplish more in one interaction.
The problem, as I see it, is that sales people rarely think about the difference between these types of interactions, and even more rarely think about which one they should execute relative to the goals they are trying to accomplish. If you need to do heavy discovery, learn about the clients business, get to know the client, or their business, or their company, or their process, it makes sense to plan for a conversational interaction. However, if your goals are more transactional, or the need is to position your solutions, commercially teach the client, demo your product, or to instigate a negotiation, it will make sense to plan for a presentation or similar type of interaction.
The issue you will have with a conversation-only interaction is that buyers often push for a presentation. I have discussed this in past posts, specifically ones called “You Are Being Judged” and “The Uncanny Value Add Conundrum”. Asking a seller to present, helps the buyer impose the frame that they feel most comfortable with; you as the vendor, and the they as the judge. In order to pull off a conversation-only interaction, you will need to telegraph the plan well in advance and get buy-in from the client before the meeting is scheduled, otherwise they will expect you to present, and their expectation will likely cause your plan to feel forced and awkward if you insist on it. Otherwise, you will have the option to abort it, and present, but that will not be likely to accomplish your goals for the interaction.
If you noticed above, many of the goals mentioned that call for a conversational type meeting are goals that generally need to be accomplished early in a sales cycle. On the other hand, many of the goals that call for a presentation, are generally goals that need to be accomplished later in the sales cycle. In order for a seller to gather the information they need and to build relationships and credibility with the buyer that would make for successful presentations, conversational interactions are vital. However, earning the right to propose and execute conversational meetings early in a sales cycle is hard to do. This is the conundrum that all good sellers find themselves in early in a sales cycle. We need conversations, but we have not yet earned the right to have them, and buyers want presentations because they feel more comfortable in those settings.
There are essentially three ways to combat this conundrum:
None of these strategies are fool proof, but if executed well, all three can give you, the seller, the opportunity to spend time on insights, problems, and desired outcomes for the buyer early in the sales cycle. This will help you accomplish the goals that you need to in order to be able to prepare and gather information for the later stages of the sales process where the focus will be on more transactional interactions, solutions positioning, commercially viable teaching, more in depth and targeted demos and working sessions, and detailed negotiations.
All of this said, one reality still remains; most interactions in long-sales-cycle processes should be only conversational, or only presentation based, not both. Selecting a specific goal for each interaction and then matching the type of meeting to that goal will help to avoid the fraught social dynamics of switching, as well as the sometimes awkward agenda gymnastics that go along with it.
Dan Greenberg · August 9, 2024 · 11 min read
Although there is much dogma and supposedly common-sense knowledge floating around about what makes a good seller, the actual answer to the question is predictably more nuanced than the dogma, and also, at odds with much of the dogma. As with many things in life, what we can measure, or observe on the surface, is often emphasized as more important than what we cannot. What seems certain is that, regardless of how monolithic evaluators, managers, and interviewers are when they measure sellers, there are different personalities and skill sets that are capable of making a good seller, and therefore knowing yourself and the type of seller you are is of paramount importance. Knowing yourself helps you lean into certain behaviors that are beneficial in the sales process, and also helps you decide which skills and behavior sets to work on developing in order to compliment your natural personality and
capabilities.
Let’s start with our old friend Daniel Pink, who I have referenced before in my posts. He is a New York Times Best Selling author, who is well known on the “sales conference speaker circuit” for a few things, but among them are his thoughts on personality and how it affects a seller’s success. He talks a lot about the importance of the traits of attunement (perceptiveness), buoyancy (resilience), and clarity (message conveyance), his ABCs of selling, but he also references quite a bit of research on how introverts and extroverts perform as sellers. After multiple studies, and much research, Pink tells us that there is no evidence that being extroverted correlates with more sales.
He starts from the somewhat prevalent assumption that in order to be a good seller, one must be extroverted, but he asserts that there is virtually no evidence that being extroverted correlates with more sales, which is potentially counter to prevailing opinions. He goes on to talk about the research and states that being introverted also does not correlate with more sales, which is likely very in line with expectations. Rather it is the people in the middle, the ambiverts, that are disproportionately the highest performers in sales.
In other words, experts, interviewers, and evaluators tend to look for bigger and more extroverted personalities who they feel can control a room and excel at social relationship building, perhaps simply because that is a noticeable and observable trait that one can base a decision on, but in reality, that noticeable trait does not seem to have any correlation with actual sales success, according to Pink. This does not mean that extroverts cannot be good sellers, it simply means that if we only look for extroverts, we miss out on all the others who may be just as good, if not better.
This is important to understand because while we are not really able to create a perfectly scientifically testable scenario to measure sales skills, we have an experience based understanding that supports the idea that those with a good social presence and perceptiveness tend to do well at developing relationships. It is important to rely on our intuition here and recognize that the research that Pink references is important in establishing this, but even if we didn’t have the research, we shouldn’t disregard our experiential knowledge. Shared experience has tended to be devalued as we have developed more capabilities in collecting and analyzing data, but that can lead to an overreliance on data that does not complete the picture. There are still things that can’t be measured and further, there are things that can’t be fully understood even by the measurement we can do.
None of this is to say that developing behaviors, and learning skills is not important and cannot improve a seller. But it is to say that it seems as though there are many different behaviors and skill sets that can work, and the key is to find ones that fit with your personality.
So, if extroversion does not lead to more sales, and introversion does not lead to more sales, what personality traits do make a good seller? Is it possible that the only positive correlation between sales success and traits is social awareness, social skills, and perceptiveness? Again, very hard to measure, but some of the data and experiential observations that we do have tend to agree with this theory. Of course, we should not forget to mention that hard work and resilience are incredibly important because, while being a passable seller may rely heavily on social skills, long term commitment to improvement and hard work are important for the best sellers.
But we should also be aware that confidence, not necessarily extrovertedness, does play a role in success inasmuch as it contributes to social comfort and cohesion with buyers. Some skills directly contribute to success, and some skills, experience, and attributes, contribute to the feeling of confidence that allows a seller to feel comfortable in sales settings, which puts their buyers at ease, and optimizes social connections between buyer and seller.
Let’s stick with Daniel Pink here for a little while as we explore some of the traits that make a good seller. Pink likes to refer to it as his ABCs of selling, and they are Attunement, Buoyancy, and Clarity. Attunement is the idea that the more perceptive and aware you are of your social environment and the needs of your buyer, the better off you will be. Buoyancy is the idea that there is a lot of rejection in sales, so resilience and hard work are important, and Clarity is the idea that we, as sellers, are no longer in the persuasion business, so instead of conveying information, our job has become to clarify points of view and illuminate what is important.
These traits make a lot of sense, and they contribute to the understanding around why natural born traits like extrovertedness don’t explain variation in performance. Certainly magnanimous people who get along well with others are good in social settings, but magnanimity, and social acuity are not specific traits, they are a combination of traits and developed skill that have led an individual to be better at social interactions on the whole. More importantly, many components of that magnanimity are learned; we don’t have to be born with them.
So, on the whole, the lesson here might be that we are looking for the wrong types of people when we evaluate sellers (hint to sales managers: stop over indexing towards extroverts in your searches); this brings up further questions for us sellers; namely, what makes me good at my job, what skills should I develop, and what kind of seller am I anyway?
Let’s use the model laid out for us by Matthew Dixon and Brent Adamson in “The Challenger Sale” to start to attack this problem. I think the way in which they define sellers makes a lot of sense and is helpful in understanding ourselves at an individual level. Keep in mind that very few sellers are one of these classifications exclusively, as you read through the definitions that I have paraphrased from Dixon and Adamson. A few people may feel that they represent three, four or even all five of the classifications, but most people will over index pretty heavily on the activities and behaviors of either one or two of the classifications, and for the ones who fall in two categories, one of the categories will likely overshadow the other, at least to a certain extent.
The book series is called, “The Challenger…”, so I don’t think it’s a stretch to imagine for those of you who have not read the books to assume that the top performers are the challengers. In fact, top performers measured were more than twice as likely to primarily use the challenger approach compared to any other approach. And, importantly, as deal complexity increased, the positive effects of the challenger approach increased. This is true, however, it is of note to mention that the other four classifications perform similarly. So, while challengers do over index as top performers, there are top performers in all categories, and the other classification perform relatively similarly to each other with the caveat that the relationship builders are the worst performers.
It is important to remember that most sellers fall into multiple categories and that many sellers fall into more than two categories. Further, it is important to remember that sellers that tend towards other profiles besides challenger can also find success. None of that is to disregard the higher performance level of challengers compared to others. Based on their research, it seems logical that developing challenger seller skills is likely to improve performance, but this is not a one dimensional activity. Each individual seller must first understand what type of seller they are, what type of behaviors they currently exhibit, and then start to understand how to develop behaviors and skills within the parameters of their personality.
It is incredibly important to understand and evaluate yourself, as a seller, before deciding what skills and behaviors to try to develop. As sellers try to learn and incorporate new behaviors and skills into their approach, they often lose touch with the basic social skills that led to successful social and sales interactions in the first place. Managers get this wrong all the time too. Many sales managers try to teach sellers the behaviors that worked for them when they were selling, but the issue is that the personality and the setting is different. Times change and buyers react to information and messages differently over time, as we discussed above when talking about outdated sales tricks, and tactics. More importantly, each individual has a different personality and relying on behaviors that are not congruent with one’s personality will come across as phony, or awkward, and nothing pushes a buyer away from a relationship faster than awkwardness and phoniness. When humans sense anything inauthentic, they immediately lose trust and your buyers are no different.
For all of the above reasons it takes careful consideration to really evaluate yourself and think about how to develop behaviors and skills. For example, if you believe yourself to be mostly a “Reactive Problem Solver” with some “Challenger” behaviors, you may want to work on developing the traits of a Challenger, but you may want to make changes to the way you solve problems so that instead of providing answers, you are listening to the problems, learning, and then teaching and reframing in ways that are commercially viable. Or, if you see yourself as mostly a “Relationship Builder”, with some “Hard Worker” traits, you may want to think about how you pivot your relationship building behaviors from being more submissive to more direct. You may also want to double down on your hard work traits so that you have more of a pipeline and therefore less reliance on your current relationships. The point is that there is more than one way to develop yourself as a seller, but the foundation of your development comes from knowing yourself, your personality, your behaviors, and your skills.
Dan Greenberg · July 18, 2024 · 8 min read
We no longer exist in a world where closing tips and tactics have much of an effect, at least not when it comes to B2B sales. This is due to information availability, information parity, and the proliferation of buying committees and procurement processes. In other words, sellers are not controlling and conveying information to singular decision makers any more. Buyers are making fewer decisions in the moment, which means that they are less influenced by emotion, and perhaps more importantly, they spend more time thinking about the internal political implications of their decisions, which will be scrutinized by many. Buyers are now responsible for telling the seller’s story internally if they want to bring their buying committee along with them. The goal for sellers has shifted from persuasion and agreement in the moment, to something that looks more like teaching a buyer to construct their own story that they feel ownership over.
In the new world of closing, sellers must train buyers to be convincing internally. They must learn how to allow the emotion of the sales conversation to be carried throughout the process by the buyer who feels bonded to the story that they have helped build. So what are the major components in this type of close?
Visualization & Urgency. It’s not so much that these two things will help drive deals to happen faster, it is that without them, deals won’t even happen. Don’t get me wrong, a seller can get lucky, and the client can have their own urgency, and the client can also do their own visualizing. But in those situations the seller just got lucky, and didn’t really have influence on the close. What I want to discuss here is how to develop these two concepts for a buyer.
Visualization:
There are four questions listed above and they are in a specific order for a specific reason. This line of questioning, asked at the right, time can trigger your client to start to think about what it would be like for their team to actually start using your solution. Visualization is a very powerful tool. As soon as your client starts to visualize, their brain will automatically start to work on justifications to help that visualization come to fruition.
This set of questions is meant to be asked at the very beginning of closing. Obviously there is no finite start to the closing phase, but it is important for a seller to understand when the problem has been fully defined, and when the client completely understands the outcomes, value, and solutions. Once that point arrives, and there are no more substantive objections; that is when closing begins.
There are two visualization questions in the set of four. The first asks the client to visualize what a world looks like in which the solution is being used. This is a tougher visualization because it is a state of reality more than a tangible situation, but it is still important. The second visualization question is more concrete and asks the leader to think about their team and how the solution will benefit their day-to-day. Before each of the questions, there are buy-in questions. You are making sure that the client tells you verbally that you two are on the same page. This gives you license to ask the more intrusive, and mentally burdensome question about visualization.
Urgency:
There is a question and a statement listed above and I have placed them in the order they are in for a reason. The first one is a bit more blunt and forceful and should be used at some point as you move into the closing phase of a deal. However, it can elicit a reaction that displays reluctance on the part of the buyer. Notice that I purposefully used the word “an” instead of “our” because I did not want to tell the buyer that I had decided for them that they were going with our solution. The question leaves their solution decision open, but it asks when they want to be able to get started with implementation.
If they show a heavy amount of reluctance, you may still have an objection hanging out there that you have not dealt with, so it is important to ask directly, and the way to do that is something like; “let me ask you this, if you decide against our solution, what is the likeliest reason you will make that choice?” If they give you a substantive reason, you can say: “great, that is exactly why I asked that question, I sensed that there was still something that we had not covered completely and now we get the chance to dive deeper into that and see if the solution fits all of your needs or not.” At this point you can launch back into your normal way of dealing with objections. If the reason is not substantive, you can address briefly and move on. You now have the second statement above in your back pocket for later in the conversation. If you did a good job of discovery throughout the process, you should have something that creates some sort of deadline or timeframe for them. You can note it and then move to the second statement.
The second statement is designed to let the client feel like they just have to dip a toe in the water. There is no problem with taking the first few steps, like getting the procurement process up and running, or having the implementation team meet the tech team on the buying side. These are small steps, but remind the client that if they may eventually want to move forward, it is important to set a timeline, and start with the first small steps in order to meet their time dependencies, even if they end up deciding against the deal later.
A huge part of both visualization and creating urgency is animating the enemy. In many cases, the enemy is the status quo, but it can also be an incumbent, a competitor, or “no solution”. If you are the one who helps clearly define the problem for the client, and helps them understand why the thing they are doing now is not working, you will have a major leg up when it comes to helping them pick a solution.
Sales managers and trainers spend a lot of time talking about making the buyer the hero, and the protagonist of the story, but good stories need a protagonist and an antagonist. Afterall, a protagonist with nothing to conquer makes for a pretty terrible story. Even if there are no deadlines or time constraints for the buyer, the simple existence of a well described antagonist can help them understand the need for quick change. If their answer to your question about timing is something like, “as quickly as possible”, that’s great, but it means nothing. Work with the client to help visualize the problems caused by the antagonist. The urgency developed by the existence of that antagonist can lead to conversations about a goal date so that you can work backwards and set a calendar that you can both work from.
Without an enemy, It’s just not a fair fight. They are evaluating your solution vs. nothing. Something is scary, but nothing is never scary, because it doesn’t exist. Sure, it might be bad, but bad doesn’t inspire emotions, scary does. In order to compete with the status quo, you need to create, describe, animate, and help your client visualize it as the enemy.
Be aware that while your individual stakeholders need to understand the risk of the status quo, your C-Level executives need to understand the lack of risk associated with what is new, relative to the risk associated with the antagonist of the story. The visualization work is what helps to define the differences between the antagonist and the solutions, and the clients contributions to those conversations are what help drive conversations around urgency.
Dan Greenberg · July 4, 2024 · 7 min read
My dad is the first sales person I ever learned from, and I learned a lot from him. He is now a semi-retired non-practicing lawyer, a businessman, a consultant, and an advisor, but he has sold a lot in his career, and knows what he is talking about. One of the first, and to this day most vivid pieces of advice that he ever gave me is that the most important thing you can do as a seller is find a quick “no”.
When he gave me this advice, it made intellectual sense. I mean, if it’s not gonna happen, then find out quickly and move on. But, as I have advanced in my career, the advice has become more and more meaningful and appealed to my understanding on a number of different levels. Not only does finding a quick “no” value your time and resources, as a seller, it makes you a much better seller because it allows you to confront scary and difficult issues upfront, and avoid hiding from them.
When thinking about how to spend our time as sellers it is easy to get lulled into equating relationships with opportunity. We all do it. It is soothing to our subconscious brains, it is easy to explain to bosses and internal teams, and it is just frankly more pleasant to talk to those who want to talk to us. The problem is that the people who are pleasant, and nice, and agreeable usually aren’t the buyers. Sure there could be a small amount of overlap, but the people who want to spend time talking to us are usually not the people who have enough internal sway to buy from us. This is not to say that there are no nice individuals who have decision making power within buying organizations. What I am saying is that we, as sellers, tend to gravitate towards the easiest and most pleasant conversations, and those tend to be negatively correlated with the ones that will get us closer to deals.
Objections and contentious relationships are often good. Real objections that are focused on the core of discussion and the reality of how a solution will interact with a problem are good because they mean the buyer is engaged, and thinking about a solution. Buyers who never object rarely buy, however, most eventual buyers object at some point in the process, because they have true concerns that they want ironed out before committing to buy.
Challenging your clients on their current viewpoints and on what is and is not acceptable to them is very important because it draws out responses that tell you if the client is serious or not, and if so, what their boundaries are. The reason that ‘challenger sellers’ are able to outperform other categories of sellers, in the well known Challenger Methodology study, is partially because they challenge conventions, but it is also because they learn the boundaries of their clients much better than those who do not challenge. Challenging is, in and of itself, a discovery tool that allows sellers to build a map to help navigate the buying organization and their concerns. That is why earning the right to challenge is so important. The challenge conversations need to be open and honest in order to draw that information out of the buyer.
Discovery is not a discrete act, and it is not a one way question asking expedition. It includes the ideas of ‘earning the right to ask questions’, ‘earning credibility’, ‘imparting commercially viable insights’, ‘asking the right questions’, ‘engaging in authentic social interaction’, and ‘learning from the client.
There is a very important difference between the clients comfort zone, and their firm boundaries. Firm boundaries are places that a client cannot or will not go, like spending more than their bottom line allows, or implementing a solution that will fundamentally change a core tenant of their business, or implementing a process that introduces an unacceptable business risk. If you advance to later stages in the process and introduce ideas and solutions that cross these lines, or lines like them, you will lose credibility and control. On the other hand, the client’s comfort zone is more about the status quo and the things they are comfortable with and understand in the moment. These are things like a current process or way of solving something, or a specific vendor that they are used to, or a company belief in an aphorism or assumption that helps them achieve success. These lines should be challenged, and crossed often. Clients who remain in their comfort zone rarely make status quo challenging decisions, so it is your job to challenge assumptions, and established realities, and the only way to learn the difference between these two major categories, and where the lines are, is by getting to “No”.
The process of getting to “No” early helps define boundaries, improve the conversation and make you a better seller. We will spend a lot more time focusing on that, and on Jim Camp’s “Start With No” concept in a latter article, but for now, I want to look more at the other benefit of challenging and asking tough questions, which is that it helps you learn which deals will not close so that you can spend your time on ones that might.
The key is that early on in the relationship, but after you have already earned a degree of credibility, it is important to search for the buyer’s boundaries by asking some scary and aggressive questions. This boundary finding tactic will help you understand if a deal is possible as well as what the rough outline of the area that the deal can fall within is. Once you have done that, you will understand the boundries and shape of potential deals.
You have to be willing to ask your client why a deal won’t work in order be sure that a deal can work.
An example:
“It looks like we are talking about all the right things, and we are on track to meet the agreed upon timetable, but I have to ask, if we were to get derailed, what would the most likely reason be?”
This type of question can seem like it would put negative thoughts in the buyer’s mind, but it’s important because the answer tells you how to proceed. It also has an added advantage. Once the buyer verbalizes potential impediments, it makes them more likely to take those impediments seriously and help to overcome them.
Another example:
“We have spent some time talking about your issues and the potential solutions, but we have not talked about the value of solving this problem for you. I want to find out if it really makes sense for you business to solve this problem now, as opposed to waiting.”
This is just an example, but it is a version of challenging the client on a potential problem with the deal that is not yet on the table. The answer gives the seller needed information, but it also causes the client to verbalize exactly why they need to solve the problem quickly. Or alternatively, why you need to move on.
The best salespeople ask hard questions and confront risk, they ask about procurement and legal, and finance. The ask about the things that will derail the deal, they ask about objections, and they ask about what happens next, and next, and next, if we agree on price.
They don’t hide from the potential problems. This overt and direct confrontation of problems is respected by buyers, and conveys a sense of confidence that makes the deals that can happen more likely, and the deals that can’t happen more noticeable.
Dan Greenberg · June 21, 2024 · 7 min read
In Oren Klaff’s very informative book “Pitch Anything” he asserts that any two individuals have perspectives, and often different ones. These perspectives govern how they each see a particular situation or thing. These perspectives, or frames, cannot coexist because whoever’s frame of the situation is more persuasive, or powerful, will be used to discuss and evaluate the matter at the expense of the other frame. This is very important because it means that if your customer’s frame wins, then the way you would like them to perceive you, your company, and your solutions will be irrelevant.
One of the most obvious and pervasive instances of how frames can collide in a sales context is the decision of which lens to view your solution through. If a client is comparing your solution to their ideal desired solution, your solution will likely always come up wanting. However, if the client is comparing it to a status quo with definable problems that are in need of fixing then the deficiencies of your solution won’t be focused on, rather the improved state that it will likely bring about is what will be focused on.
This is an easily understandable collision of frames for many sellers and so it is a good way to discuss the concept; if you, as a seller, are not constantly ensuring that the conversation is framed around what needs to change for the buyer, then it will likely end up being framed around whether or not your solution is the right solution, or the perfect solution. And, if that becomes the case, you have a much higher likelihood of losing.
Another way to think about this is what I once heard Lou Paskalis, former Marketing Executive at American Express and Bank of America, and current Ad Executive, talk about, “You can’t sell what’s in the bucket until you sell the bucket”. What he meant by this is that if the client doesn’t buy into the frame, that it is your job to establish, that their current status quo is bad for them and their organization, then, it just won’t matter how well you pitch your solutions, you aren’t likely to get very far.
The frame that a seller is trying to impose on any situation is a frame which says that the buyer is currently in a bad situation and that they need a solution in order to correct the problem. If this frame guides the conversations, then the seller has a chance to be influential, however, if the frame is more like the buyer evaluating possible solutions just to see if anything strikes their fancy, then the seller has very little chance of being influential, because the buyer is not focused on their problems and the issues with their status quo.
I have referenced the “all-knowing judge” in previous posts, where the client positions themself, knowingly, or maybe even subconsciously, as the judge of your solutions by saying something like, “OK, let’s just get to the demo”. This is a frame that the buyer is trying to impose which positions them in a comfortable place of judgment, and the seller, as a vendor, like all other sellers. This, as a frame, is great for the individual across the table, but bad for you, as the seller, and likely bad for both the buying organization as a whole, and obviously, the selling organization.
There are other types of frames that get used in sales settings as well.
A moral frame is used when a person believes they have law or morality on their side. A person using a moral frame tries to position their way of thinking as the only way to think. Moral frames must be pushed back on powerfully with competing frames.
An analytical frame uses logic to show that the other side is thinking about something incorrectly. It can also drag a presentation into the weeds which will cause you to lose your audience. Analytical frames should be addressed by quickly answering questions and at a high level, and moving back to a frame that focuses on the buyer’s problems.
A time frame can be used to wrestle away frame control. Time frames tend to set artificial time limits or deadlines, and ask the other party to adhere accordingly. Being brief and engaging proactively usually avoids this type of frame being used.
There are a number of other types of frames that can be used by sellers to control conversations. A prize frame positions your team’s time as incredibly valuable, and an intrigue frame leaves interesting information uncovered. However, buyers tend to lean very heavily on a few types of frames that you are likely to come across over and over again. These are the ones mentioned above, and it is important to be familiar with them and how to handle them.
The other important takeaway when it comes to framing is that frames do not last forever so constant reframing is very important. Salespeople tend to make one pretty serious mistake. Once the problem has been framed and discussed, they tend to forget to bring up the framing conversation again. They move on to their solutions, they get comfortable, and they rattle off a list of solutions, products and features, with the understanding that their client will be connecting them all back to the problems throughout the presentation. This understanding is misguided. It is not how human brains work.
Your buyers are not experts in your solutions like you are, so they are just trying to take in information and they do not have the ability to take in new information and also consistently relate it back to something that was discussed earlier.
As a seller, you have a consistent responsibility, I mean 10–15 times in a 30 minute presentation, to reframe your presentation of solutions around their problems, and tie it up in a neat little bow with a picture of what the desired outcome will look like if they adopt your solution. Another way to look at it is, every time you introduce a solution, or feature, or product, it has to be a response to a problem, and it has to lead to a detail-free, comfortable and safe outcome that can be visualized.
You can think about using phrases like the following every single time you introduce a feature, or product, or solution.
“Earlier you shared with me that you were struggling with such and such, which actually aligns nicely with something I had planned to show you anyway…”
Or.
“Something we hear consistently from others in your industry is such and such. Because of that we built this product into our overall solution set and I wanted to show it to you…”
Or.
“We hear a lot of your peers talk about such and such, is that issue top of mind for you as well?
Only after you get buy-in on the issue that you are surfacing should you then show off the product or feature that you had planned to. If you don’t get buy-in on the problem, showing the feature will cause your audience to lose focus and care less, and it will cause you to lose control of the room.
Lastly, don’t forget the outcome. The buyer has to think about what the state of the world will look like when they have adopted your solution, and no longer have to deal with their problem. If they leave the situation thinking about the problem, they will leave with a negative subconscious association with the solution, and you don’t want that. They are not likely to put problem, solution, and outcome together in their own mind because that’s not their job. It is your job to paint the picture for them, all the way from problem, with buy-in, to solution, to visualizable outcome.
Dan Greenberg · June 7, 2024 · 8 min read
Taking control of a meeting is not easy. Many sales books talk about how important it is to keep control of encounters. Very few talk about how to do it. Emotional IQ, and perceptiveness of the buyers’ emotional states at any given time go a long way to giving sellers clues about how to handle situations. But it is easy to get caught up in the nuance of power dynamics and forget that sometimes taking control is as simple as dictating the setting, the agenda, or the format of the meeting.
In the early stages of a relationship it is hard to get a sense of individual buyers and what incentivizes them, but there are advantages as well. In the early stages of a sales process the buyer does not yet know how interested they are in pursuing the relationship. Because of this, buyers often choose not to assert themselves, which leaves the door wide open for the seller to take control and it is important to do so. Chet Holmes, author of “The Ultimate Sales Machine”, and architect of many well known sales team success stories, goes to great length in his book to explain that if the buyer controls the meeting or the process, the sale is very unlikely to happen.
Due to the inherent limitations of knowledge early in the sales process, it is important to seize the opportunity to take control over meetings and interactions in the most simple way possible. This means things like asking people to sit in certain spots, setting the agenda and talking through the goals and planned outcomes of the interaction, and dictating how the current interaction should fit into the broader relationship.
It is important to iterate defensible reasons for taking control and for individual asks. An example would be asking a group to get up and stretch because a meeting has been going on for a long time, and dictating that the meeting will resume in 15 minutes. It is important to look for buy-in from others once you have asserted control, but the best way to ensure that the buy-in will happen is by displaying calm and confidence as you assert yourself.
I have laid out some simple strategies for taking control in the early stages of relationships, and I will cover the more nuanced latter stages in a later blog. For now, let’s move on to giving up power strategically which is even more tricky. Giving up power on your own terms can be a very useful tool for a seller. It can be used to draw out information, as well as to increase long term ability to hold onto power. In order to give up some power, you need to be in control in the first place, which we covered above. Control allows you, as a seller, to frame the interaction as a situation where there is a mutual benefit to be achieved rather than a situation where you are need them and their money, which automatically makes people run the other way. However, there are times where strategically giving up control makes sense, and I want to briefly touch on two of them.
Here is the first: Many buy-side participants in the sales process are interested in power, status, and playing the alpha role either by rote, or because they care about how they are perceived internally by their own buying organization. This means that in practice, they don’t actually need to be the alpha in the room, so long as they preserve their alpha status relative to the buying organization. This reality can work nicely with the incentives on both sides of the table. You, as the seller, can ask questions that you know to be well within the domain of expertise of the individual trying to retain that status. Further, you can direct those questions at the alpha, and comment on the alpha’s ability to help move the process along given their expertise and handle on the situation.
When questions like these are asked, it is important to step back and create space for the alpha to answer. If you try to step back in before they are done, you will just end up ruffling feathers and alerting their conscious brain to the fact that there is a power struggle going on, which will cause them to entrench and make your situation tougher. If you do allow the alpha to talk through the answer and the situation and allow the alpha to lead for a couple of minutes, often, they will simply hand the floor back to you when they are done because they feel less threatened. But even if they don’t, you will be free to take control back and move to whatever topic makes sense as soon as the issue that you passed to the alpha is covered. Your voluntary relinquishment of control will give you license to take it back when you need it.
It is important to be aware of when you are doing this. Pick your spots and do it at a time where there is not already an active power struggle taking place. If you do it in one of these moments, you may lose it for good. You also want to make sure that you do not do it in a situation where two hopeful alphas, both on the buying side, are engaged in their own struggle, because they will use the opportunity to drag the group into their battle. The point is to look for opportunities where you are completely in control, and then voluntarily give up power in a very well defined and well structured way so that you have the ability to get it back. Doing this from time to time will keep alphas on the other side of the table at bay and help you in the long run. It will also help enhance your respect and trust amongst the rest of the group as you position yourself as more of a seamless cohesive entity with the buying organization.
Here is the second: In many scenarios it is important to keep control in order to keep a firm grip on power. One useful tool when trying to hold onto power is asking leading and assumptive questions, and limiting the scope of possible answers in order to stay in the driver’s seat. But, as mentioned above, there are also times when it is important to give up power in order to get information. Once you ask a good open ended question to a truly receptive client, try to indicate that you have handed over control of the conversation to them on your own terms. Let them know that you are looking for their guidance as to where to take the conversation because you are an expert in the industry and the tools that clients use, but only they are an expert in their business and where they truly want to get to.
This proactive relinquishment of control gives the client license to be more open, but it also gives you the opportunity to reassert yourself later when the conversation shifts again. It is important not to be afraid to give up control at these moments in the sales process, because if you don’t give up control at some point, you will have trouble opening the buyer up to a point where they will really share with you.
The best times to give up control and ask truly open ended questions are one-on-one or in small group settings. It is also good to think about doing it in conversational and social settings. These commitments to learning through giving up control will give you the ability to keep control later on in the large group meetings and presentations where keeping control is more necessary and beneficial to the process.
Dan Greenberg · May 22, 2024 · 5 min read
The question is not, “What is the secret to sales?” The question is, “What is the secret to this sale, for my selling style, at this moment, with this client?”
People who write instructional books don’t often change their ways when they read the instruction of others. What is my point in telling you this? The point is that some people are in the right place at the right time and some are not. Some are smart, and some are not. Some work hard and some do not. Skill, intelligence, and hard work give you more opportunities to be successful, but they don’t correlate perfectly, or even all that well with success, for the most part.
Generally, when we see successful people, all it means is that they found success earlier in life, and were therefore able to build off of that success and create more compound success. I don’t want to take anything away from any successful person, because much of success involves putting yourself in the right place at the right time, using skill, knowledge, and a lot of hard work. It also takes, in the words of Chet
Holmes, successful sales executive, and author of The Ultimate Sales Machine, “pig-headed discipline” in order to position yourself for success and learn the necessary skills.
But that does not mean that all of those who are successful have skill and work hard, and it does not mean that all of those who are less successful lack skill and don’t work hard.
It is worth it to contemplate the idea that those who find success early often do it in their own way, very independently, which reinforces for them the idea that they do not need advice from others. Then they cash in on that early success, some of them eschewing innovation and development going forward in favor of what worked in the past.
On the other hand, those who build more slowly to their success often find a patchwork of information and individuals to help with the journey. They combine information from different sources and people and situations to help in their journey. This improves diversity of information, and helps develop more learning paths and skill sets rather than focusing on single source information. Take mentors for example. What is a mentor anyway? A mentor is a concentration of information; a single source. This is not to speak negatively about mentors in any way whatsoever, great mentor relationships can be incredibly beneficial for both parties. But a concentration of information means that you are only getting one point of view. It is important to diversify viewpoints across people, materials, and situations.
All of this is to say that you shouldn’t take any set of information as gospel. Glean what you can from it and then seek additional points of view. This goes for experts as well, because, as mentioned above, many had early successes and have traded off the currency of that success, so their perspectives tend to be limited.
Throughout the various articles that I post, I work hard to provide a unique perspective; the perspective that explores what your behaviors cause the buyer to think, and what buyer behaviors should influence you to do. But there are, of course, other perspectives. Other ways to think about sales cycles, and other ways to take in information.
What you decide to focus on in your learning journey is very important. But if you try to take in too much, you will likely end up with nothing. We don’t have the ability, as humans, to change our behavior drastically, and over multiple areas of focus. This means incorporating knowledge from diverse sources into your development, but then synthesising small pieces of that information, and integrating very specific motions into your behavior in small doses.
Becoming a … master is not about learning 4,000 moves but about doing just a handful of moves 4,000 times. — Chet Holmes
As you progress and develop skills as a seller and as a business leader, it is important to think systematically about how you want to implement your learnings into your day-to-day behaviors. The key is to take things one at a time. If you try to adjust a lot of behavior at once, your brain will not be able to handle all of the change and it will revert back to what you are comfortable with. Assuming you are looking to improve, the things you are comfortable with are exactly the things that you did before embarking on your improvement journey.
Pick one area, one skill, one behavior, and build a way of thinking around that area that helps you key in on and concentrate on situations that are developing in a way that will call that skill into action. Focus that improvement area around a sales situation you find yourself in often, and then position it in a way that suits your selling style, your clients, and the types of settings that you come across. Then train yourself to go through the mental steps necessary to change the behavior and commit those mental steps and behavioral changes to your memory and to your action plan.
No one improves at anything overnight. Finish a behavior modification to a level that you feel satisfied with, and then work on another. No matter how much pressure you are under to perform now, imagine being at the same level of output 5 years from now, and what that pressure might look like. Allow yourself the time to improve at a rate that is conducive to actual long term improvement and your future self will thank you.
Dan Greenberg · May 10, 2024 · 7 min read
There are a few excellent negotiation books out there. There is “Negotiation Genius” by Deepak Malhotra and Max Bazerman, which focuses on the preparation and calculations that go into a negotiation. There is “Getting to Yes”, by Roger Fisher and William Ury which focuses on the psychology of negotiations, and there is “Start with No” by Jim Camp, which is not only one of the best negotiation books out there, but also one of the best sales books out there, and it focuses on the conversational groundwork needed to set boundaries and have productive conversations with partners and clients.
I highly recommend all three of the books above but I want to spend a bit of time in this article focusing on a concept, and a less talked-about book written by Herb Cohen, called “You Can Negotiate Anything”. I think we can learn a lot from this book due to its simplicity, and it’s focus on recognizable and controllable circumstances and actions. I want to take the liberty of adding a bit of interpretation to the book, but I’ll start with a quote from author and former FBI hostage and SWAT negotiator Chris Voss, “Negotiations are always over time. That is the frame to think about it through. Money is {just} the label.”
Let’s be clear and say that negotiating is not selling, and much of selling is not negotiating, but the principles used to understand the psychology of those sitting across the table from us in a negotiation go a long way to informing our sales approach. When we step back and understand what Chris Voss is teaching us, we can see that what he is really saying is that the party across the table from us has a deadline. If they didn’t have a deadline, they wouldn’t be taking their valuable time to talk to us about the thing that we are trying to sell them. Their deadline may be nebulus, it may be far off in the future, and it may lack urgency, but nonetheless, it exists. This is incredibly important, because if our deadline is perceptibly more urgent and noticeable than theirs, they will always win the negotiation, and they will also, always have the upper hand when it comes to power dynamics.
Herb Cohen’s book is structured around three key ideas in a negotiation. They are; time, information, and power. However, if we take a look above at what we just talked about, we realize that they are all one in the same. Sure, information and power take on a few added elements beyond their relationship with time, but the crux of the information dynamics has to do with which side knows more about what the other side really needs, and more importantly, how quickly they need it. Meanwhile the crux of the power dynamics have to do with who is more constrained by urgency, and therefore who needs a deal sooner.
Time: Sellers must be prepared to be more patient than their buyers. Of course it is important to accentuate urgency for the buyer, based on their understanding and needs, but urgency cannot be artificially created. Deals always get done close to deadlines, according to Cohen. This is because human nature causes us to delay decisions, hoping for more information, until we are forced to make them. This means that sometimes, regardless of efforts to surface urgency, a seller’s patience and lack of neediness will end up winning the day. It will signal to the buyer that their urgency is actually lower than the buyer’s urgency, and this can help make a deal a reality because it shifts the power dynamics. Sellers must be willing to voluntarily push the deal deadline and remove time pressure. This means having contingency plans with other deals so that quota does not suffer. As sellers, we need to have a healthy pipeline to rely on when we are forced to exercise patience, and we also need to show perceptiveness and understand the difference between a power dynamics struggle and an uninterested buyer, so that we know when to focus on urgency or time-pressure releases, and when to move on.
Information: Cohen talks at length about helping to form opinions rather than trying to give others information once their opinion is already formed. Of course, this makes logical sense, but oftentimes we leave things like price negotiations, and hard conversations until the end, because we are afraid of the confrontation that may be caused by them. If a deal has a fatal flaw, it is better to learn about that flaw early on instead of wasting time. But more importantly, if a deal does not have a fatal flaw, it is also good to get as many issues on the table as possible early on so that your conversation with your buyer is about the total value equation rather than just pieces of it. This is important for connecting price to value rather than just racing to the bottom against your competitors. It is also important because as you curate the information that you share and highlight, you can start to learn about your clients needs and their urgency around those needs, while at the same time signaling your lack of urgency. I’m not advocating price negotiations early in sales processes, but I am advocating price conversations that allow your buyer to calculate value. That way price negotiations later on will have much less ground to cover.
Power: A seller’s main job, from the perspective of control over power dynamics, is to remain calm, and to never betray a sense of neediness to the client. The knowledge that a seller has about the industry, the product, and the client’s needs and desired outcomes serve to convey confidence and control. A seller’s composure and confidence in their current pipeline, and ability to generate more pipeline convey a lack of need. This attitude and approach tell the client that your deadline is farther out than theirs, which serves the purpose of keeping you in the driver seat and highlighting the importance of the client’s deadline.
It’s all about time: Herb Cohen’s framework for thinking about a negotiation is very helpful, but it becomes even more so when we understand that everything discussed eventually ties back to time in the form of patience, and lack of need. Information about time, the power of asymmetric urgency, and time itself can be used to the sellers advantage all throughout the sales cycle, so long as dynamics of the interactions do not slide backwards into the familiar and indefensible posture where sellers need buyer money to meet their quota. This frame is disastrous for sellers because it gives up information about urgency, it gives up power, and it allows the buyer to be in control of time, and therefore, the deal.
Although the negotiation, as we commonly understand it, is only a small portion of the sales process, the principles that we learn from negotiation, and the skills that we sharpen when thinking about negotiation, can be used throughout the sales process. These skills help us position the buyer, and the conversation, within a frame that is advantageous for getting a deal done.
Dan Greenberg · April 25, 2024 · 8 min read
There are two basic lines of thinking in sales training and in sales literature. One is that objections don’t actually exist and if you are hearing them it just means that you did not do a good enough job selling so it’s time to return to discovery and presentation. Another line of thinking is that no matter how much you do right, you are going to get objections. Every client will have objections, and you have to prepare for them; I’ve seen 4-step plans, 5-step plans, and 7-step plans, and everything under the sun.
So which is it? Prepare yourself for a disappointing answer from yours truly. Both are right and both are wrong.
Both are right because it is true that sellers who do a great job with discovery, ask the right open ended questions, and do the right kind of follow up, will open up conversations that cover most potential objections. These objections can be discussed in discovery, when the seller is in control, and are less likely to be raised again as formal objections later on, when the seller is not in control. At the same time, new buyers can enter the mix, new information can be presented and focused on, and people can change the way they think about things over time. Plus, we are human, so it is possible that not everything gets covered in discovery and presentation. For these reasons, it is entirely possible to do most things right and still have objections come up towards the end of a deal cycle, so it is important to have a plan for how to deal with them.
Both are wrong because, although some trainers and writers may take buyer mentality and behavior into consideration, neither of these high level summaries of the matter take these factors into account. Basically, what this means is that objections exist because buyers are independent people, and the way we deal with them is important, whether it is informally, early in the process or more formally, later in the process.
More to the point, not all objections are the same, and identifying the nature of an objection is key when it comes to dealing with it. There are real objections that actually express a true reservation about the solution, the value equation or the situation, but there are also a number of other kinds of objections that are not about solutions and are sometimes more innocuous than real objections, but can sometimes be more insidious.
The first type of objections are real objections. They express a true reservation about your solution, it’s fit for the problem, the situation, or the value equation. These objections are real, and they tell you that you need to return to the process of discovering more about the problem and ideal outcome before talking more about your solutions and how they can help. These objections come from a real place where the buyer is trying to genuinely make the right decision, and regardless of if they are leaning towards buying or not, a real objection is still a real objection and should be dealt with. I will be writing more in future posts on handling real objections.
Social dynamics based resistance is when a buyer resists you or your solution due to social expediency, and not due to the deal components themselves. These can be things like the buyer wanting to show an internal group that he is being tough on the vendor and preparing to negotiate so that he can look good in front of a boss or team. This can also include situations where the buyer does not have enough power within the organization to make a decision and rather than admitting that, they prefer to object so that there is a reason the deal doesn’t get done other than their lack of power. There are a number of other social and political dynamics that can cause resistance. It is important for sellers to identify these types of resistance, and understand why they are happening, because the solution to the problem is almost always to change the makeup of the individuals that are in the room for the next meeting. This sometimes means getting to new decision makers and sometimes it requires limiting participation, but if social dynamics is the problem then the dynamics themselves need to be changed.
Prospecting resistance seems like it would only happen in the early stages of a sales cycle, but as new people enter the mix, and as a cycle advances to new stages, prospecting resistance can pop back up. It usually manifests itself as resistance to meetings, and lack of commitment to events and venues of choice. This is essentially the client saying to you, “hey, I have other important things going on that are more of a priority right now, and I just don’t have time to deal with this at the moment”. This is partially a power play, but it is partially the ‘pre-programmed gatekeeper’ in their brain expressing resistance to something new. This is human nature and the way that we guard ourselves against having to exert mental energy to consider new things. These activities can be prospecting resistance, and they can also mean that the client is legitimately not interested. It is important for you to understand which is the case. Prospecting resistance can be handled by persistence and a focus on client problems.
Fear of commitment is essentially the buyer finding a conceptual objection that sounds legitimate in order to slow the process down. Just like in relationships and other types of social interactions people are afraid of change and are especially afraid of rapid change. Sometimes resistance is just an effort to delay a process so that the buyer or the buying organization does not have to confront the fact that they have already decided that this is likely the right solution. They are legitimately scared of making the wrong decision, but don’t necessarily have a well founded reason why. But they are also scared of the perception of making a big decision too quickly and being blamed for making a hasty decision if it goes wrong. Fear of commitment resistance can be dealt with through urgency creation, patience, and sales process rigor.
Those who argue that objection handling does not exist will tell you that objections are borne out of a failure on the part of the seller to adequately position the product or the solution. The argument essentially says that objections come from one of two places. One place is a buyer who wants to buy but has not been properly sold, and the other place is a buyer who does not want to buy but is not willing to confront the situation and be blunt with the seller. This means that the seller has created the environment for both types of apparent objections. In the first situation they have not sold well enough, and in the second they have failed to recognize an uninterested buyer.
There is a certain degree of truth to this as I mentioned above but it does not mean exactly what it seems to mean. It does not mean that objections don’t exist and it does not mean that we should not spend time thinking about how to deal with objections. It’s not that objections don’t exist per se, it is that they are a natural part of the conversation that is your job to stimulate. Objections can be good, and they are not a discrete part of the sales process. Of course, it is better to draw them out on your own terms earlier in the sales process, than have them come out in more surprising ways later on in the process, but regardless of the timing, they are still objections, and they still need to be identified and handled. The point is that the only difference between discovery and objections is that discovery is a conversation on the seller’s terms that addresses objections, while objections, as we are used to thinking about them, are brought up by the buyer on the buyer’s terms and demand that the seller to address them.
It is your job, as a seller, to ask the scary and challenging questions, and confront the possible situations that could kill a deal because if you don’t do it, a doomed deal will still get killed, but you will spend much more of your time and resources before you find that out. The scary questions bring about real objections on your terms so that you can deal with them, and perhaps more importantly, they bring about the objections that are unresolvable so that you can move on and spend your time and resources on deals that you can close.
Dan Greenberg · April 3, 2024 · 7 min read
Providing a client with insights that help frame their thinking is a vital tool in any sales process. It helps frame your message, and it keeps the conversation focused on the buyer’s needs.
Why is this important?
Your buyer is judging you from the moment your interaction begins. It’s the only way they feel comfortable. If a person feels like they are being manipulated, they will experience a lack of control, and that is something that we, as humans, have been trained to, and have evolved to avoid at all cost. Therefore, in order to remain in control, and in order to avoid being manipulated, your buyer is judging you and placing you in a bucket with all other vendors who also need to be judged. If they weren’t judging you, then they would be taking direction from you, and that would not be acceptable to them.
They are judging your trustworthiness, your intelligence, your knowledge, your ability to add value, your likability. They are judging your company’s trustworthiness, its organization, and its values. They are also judging your product’s specs, its reliability, and its relative features and benefits. On the surface, they are doing all of this in order to help make the most informed decision possible. But, the much more dominant, albeit partially subconscious reason for all of this judging is that they are building a case against you. They are building a case against all of their potential vendors because it will help them justify their eventual decision. They will eventually have to justify their decision to themselves, to their coworkers, to their boss, and to you. Their decision will be made mostly on emotion, but the justification will have to exist. We can intuitively understand this because we all do it in our own lives. Every time we make a significant decision, we almost involuntarily begin building the justifications and arguments against the other outcomes in order to be able to explain our decision clearly if we are asked about it.
Additionally, the buyer is the hero of their own story, as we all are, so building a case explaining why all vendors are deficient allows the buyer to position themselves as the hero who makes the solution work in the end. Partially, they are setting themselves up to be the hero, and partially, they are already laying the framework to be able to explain away any accusations should the eventual decision go poorly.
Why is all of this important?
First of all it is important because, as a seller, you do need to give your client enough information that they can make a rational justification for buying. This is the simple and surface level read of the situation, and although there is more under the surface, it is still important. This is where differentiators, and outcome selling come into play. But let’s be clear; in doing this, you are not trying to sell to your buyer, you are teaching your buyer to make the case for buying your solution. This is a subtle but hugely important shift in the way you talk to your buyer. You can imagine yourself as their sales trainer. The majority of conversations they have moving forward will be without you in the room, and so it is important for you to think of yourself as preparing them for those conversations. You will do a better job accomplishing this if you think of yourself as a trainer rather than a seller, and you will naturally move the buyer into a more collaborative mindset. You are not selling to your buyer, you are training your buyer to sell.
The second reason that this is important is that it is your job to jostle the buyer out of their state of judgment. A person in a state of judgment has a closed mind. They are in charge and they are the one who knows everything and is deciding what is best. That is not a collaborative mindset, and it will not allow you to influence the buyer in any way because they are already in that closed mindset. Training the buyer to sell is helpful in changing this mindset but the best way to nudge your client out of the judgment mindset is through commercial teaching of insights.
Bringing insights to the table focuses the conversation on how to think about your client’s business. It frames the conversation in a way that allows the client to talk about what is important to them, but to do it in a context that accentuates two very important things; number one, where they would like to end up, and number two, what they need in order to get there.
It is incredibly important for the client to talk about these two things because it teaches you, the seller, where they want to go and how they want to get there, but maybe more importantly, it frames the conversation around the client’s needs and wants which leaves the power and control of the interaction in your hands. So long as the conversation centers around their needs and wants, your solution could potentially be their answer, which means they need you. As soon as the conversation shifts to your solution, they become the judge again. They start thinking about how and why your solution is likely not the answer, and in that conversation, you become the needy one, and therefore you lose control.
Teaching, and a focus on insights, are what allow you to remain on level ground with the client and keep control. As soon as you start selling your solutions, the client becomes the judge, and you, the judged. Commercial insights should be developed from your organization’s understanding of the client’s industry and its needs. They should focus on ways to save money, or on ways to increase efficiency and drive more revenue, and they should leverage your organization’s industry knowledge and past work with companies similar to your client. The insights should focus on the achievement of outcomes that challenge your clients status quo thinking. There are two very important ideas to keep in mind as you are presenting and teaching commercial insights.
Dan Greenberg · March 20, 2024 · 8 min read
We live in a world where sales is becoming harder; real sales, the kind where you truly influence the outcome. Truly influencing deals is getting harder because information is becoming ubiquitous. Buyers all read the same things, think about problems in the same way, have access to the same information, and are expected to have fully formed opinions on how to confront problems before ever talking to a seller. They don’t have the organizational political leeway to rethink solutions based on learnings from an outside source, let alone a biased one that is hawking a product. So, in order to improve or maintain their internal standing, buyers use sellers as pawns in the internal story that they tell their organization. The story is about how they, and they alone, understand the problem and the desired solution, and are comparing vendors and prices in a way that will benefit the organization, thanks to their diligence.
This reality was not always the case. Buyers used to need information from sellers, and old sales strategies and playbooks reflect that. In that world, it made sense to talk about differentiators, and unique value, because buyers simply did not know it on their own. But the world has changed, and we, as sellers, have to as well.
Daniel Pink, a seven-time New York Times best-selling author, who spends much of his time talking about human psychology, and behavior as they relate to business and sales says that sellers are no longer in the persuasion business as they once were. He says that instead, sellers are aggregators of information and must do so in a way that makes their point. He is right, but I would put it differently. The job is no longer to persuade people that our products are better, the job is now to persuade people that we, as human beings, are valuable to them; that we are credible; that we have a point of view that is helpful to their business; and that we have the integrity to help them with decisions regardless of whether it is commercially beneficial for us. We are in the business of positioning ourselves so that when the buyer recognizes an issue with the status quo, they know who to turn to in order to have the best possible conversation about their problems and desired outcomes.
All of this does not mean that we, as sellers, should idly sit by and hope that the buyer gets to that realization on their own. We can be proactive about pointing out problems, and illustrating inefficiencies, but the buyer must come to the point where they recognize and assess the problem before they will decide how to go about fixing it, and the only people they will truly confide in regarding how to fix it are those who have proven credible.
Buyers’ reactions to the consistent barrage of outreach, combined with their unprecedented access to information is simple. They have put up filters and shields to block out salespeople. It is not because they don’t want to talk to salespeople, rather it is because salespeople are talking to them about the wrong things and in the wrong way. Buyers don’t need information and proof of product anymore; they have all of that in spades. They need consultation and analysis of their business and the possible outcomes. Salespeople are talking about the wrong things and leaning on the wrong tools.
There is a huge disconnect between what a buyer in the modern business environment needs and what sellers are talking about, and sellers who don’t pivot are driving a wedge further and further into the problem and pushing buyers away. Twenty years ago, you still had old school sales gurus pushing old tips and tricks but most of them are out of the game now, and people realize that those old tips and tricks don’t work anymore. So, what has replaced them? A whole lot of nothing. Outdated tactics, like The Sharp Angle Close, the Time Limit, and many others, don’t work in a world of information parity, but the world of sales learning and training has not replaced them with an understanding of how to close business given the new world we find ourselves in.
What these closing tricks have in common is that as buying organizations have developed more robust procurement processes, and as information has become more readily available, buyers have become less amenable to tricks and in-the-moment tactics. Not only have buyers had access to stories and information that tells them that these tactics exist, they are exposed to a far greater number of approaches, due to the prevalence of email and video calls, and they simply have more access to information about the seller, their products, their competitors, and the seller’s organization.
This increase in information, and experiences has made it so that many of these techniques have lost their effectiveness. The reason they have lost their effectiveness is because closing tactics are inherently designed to be an end run around the buyer’s filters and defenses, and to work in the moment when those defenses are not present or are ineffective. However, since fewer and fewer decisions are allowed, or able to be made in the moment, by a single buyer, and since many buyers are desensitized to the tactics in the first place, closing tricks and tactics have largely become less effective over time; significantly less effective.
So how is a skilled and thoughtful seller meant to respond to this reality? Management still expects a lot from sellers, and even though traditional pressure closing does not have the same effect it used to, management still expects sellers to be “good closers” and “more aggressive”. They remember the “old days” when there was correlation between aggressiveness and closed deals.
None of this is meant to claim that hard work and thoughtful selling can’t drive better and more sales for individuals and organizations. In fact, reliance on traditional sales principals is the only thing that drives sustained success, but the simple throughline from aggressive and sometimes uncomfortable closing tactics to better numbers just doesn’t exist anymore. The idea that aggressiveness, can drive short term results, just does not manifest in a world of buying committees and greater information parity between sellers and buyers.
We can’t be focused on trying to change individual peoples’ minds about our solutions because people don’t change their mind because you prove them wrong or convince them of something. People only change their mind when their incentive structure forces them to do so. We need a new set of tools and a new mindset that incorporates traditional and proven sales principals, but rethinks closing in a way that is congruent with the changed buyer landscape that we now encounter.
Sellers used to learn about discovery, and about objection handling, and about relationship building, and then separately about closing, but it is becoming more and more obvious to those in the business that these elements just do not exist as discrete stages anymore.
Discovery, objection handling, and relationship building are consistent parts of the sales process, and no longer discrete stages. They rely on an understanding of the buyer’s business, the buyers themselves, and a broad range of knowledge about competitors, products, and value. While a few well-timed questions, and well-rehearsed responses to objections used to set a buyer at ease that a seller understood their business and was listening, the significant amount of exposure that buyers have had to seller’s overtures have turned good questions, responses, and social forays into trite wastes of time. Good discovery has become about the ability of a seller to earn the right to ask questions, and to show the buyer that they are able to engage in a conversation that is productive at a conversational level. Good objection handling relies on thorough discovery and thoughtful problem development. And, good relationship management takes much more social acuity, and is much less transactional.
And then there is closing. Closing just does not exist as a discrete stage in the process anymore. Of course it exists, but a seller attempting to ‘close’, in the traditional sense of the word, has likely already won or lost the deal; and the ‘close’ will have very little impact on the outcome. Closing no longer happens on the spot, it happens throughout the sales process, and it happens in the mind of the buyer more so than ever before. The buyer comes to the table with more information and more experience, and although sellers can be just as influential, if not more so than ever, it takes a specific type of perception, and opportunism in order to take advantage of those chances to be influential.
Closing is no longer about convincing a buyer to buy, it is about selling your own value to the buyer, as a person. It is about how good of a job you do reminding the buyer about problems and desired outcomes so that they don’t have time to worry about the minutiae of products and solutions. Most importantly, once you have sold yourself, closing becomes about visualization. Specifically, it becomes about helping the client paint a picture in their mind that highlights the problems associated with the status quo and emphasizes the merits of their desired outcome.
Dan Greenberg · March 7, 2024 · 7 min read
It has been drilled into us that differentiation is the key to success. There are many books and articles written on the subject, including Jack Trout’s ‘Differentiate Or Die’, which, dramatic as it sounds, is a good read. The issue for sellers is that your buyers just don’t believe you when you tell them how differentiated you are from your competitors. Why should they? They may have been persuaded to explore your solution because of a marketing message, and they may be interested in a solution more generally, but hearing it from you is different; you are biased. As soon as you start talking about differentiation, you are just like every other biased sales rep they have ever talked to. And, the fact that you are biased leads to something much worse than disbelief, it leads to intellectual resignation and apathy.
Your buyers are rarely thinking what you think they are thinking as you sit there continually trying to reinforce logical points about your differentiators. In fact, most of the time they are not really thinking at all. Or, at the very least, they are not thinking about you. You are sitting there trying to convince them that you are right, and they are sitting there thinking, “Who is this guy, why is he here, and what’s his name again?” Obviously that’s an exaggeration in many cases, but the point is that your clients care a lot less than you think they do. You are just one of a number of people who will talk about why their company’s solution is the best. Differentiation is certainly important, but it is important at the company level and the marketing level. You and your business need to know what you are good at, where to focus, and how to attract attention, and this can only be done with focused, differentiated messaging that highlights strengths and areas of distinguishment. The issue arises when differentiation becomes the goal of sales interactions.
When you finish a pitch, or a meeting, or a conversation with a client, you may do a debrief, or think about it for a while after, or talk to your manager about it. But do you know what your client does? Nothing. The answer is nothing. Well nothing that has anything to do with you, anyway. You are out of sight, and out of mind, faster than the client can move their mouse cursor to the red hang up button at the bottom of the zoom screen. They may remember your name, maybe, but they won’t remember much about your products and they certainly won’t remember, or care, about why you are differentiated from your competitor.
Yet, how much time do you, and your managers, and your sales trainers spend talking about how best to differentiate your products, and how to describe the value that you add for the buyer and the client organization. A lot, I assume, that’s what most sales organizations spend the majority of their time training on. And I get it. Client-facing individuals do need to be able to explain value and differentiators in very clear and concise ways, but convincing a buyer to buy takes a lot more than building a logical case for your solution.
99% of the time when you are done talking to a client, they place you and your product in the mental filing bin that is reserved for all vendors, and as much as you think your product and solution may be differentiated, they just don’t see it that way. Sure, you may actually be different, but do you really think that sellers at your competitors didn’t come in and explain why they were differentiated? Do you really think that they are too inept to build a presentation that shows off why their product is better? So, why would the client believe you over them? If everyone is differentiated and provides unique and superior value, then no one is differentiated and no one provides unique and superior value. So, the answer is that your client won’t believe you. They won’t care. Your pitch is the exact same to them as everyone else’s pitch, and it will be received with apathy, just like everyone else’s. You imagine your company to be differentiated from competitors, because that is your job, but to your client, you are the same as all the other vendors.
In addition, buyers are just simply jaded. As the internet has become ubiquitous in our work lives over the past 25 years, things that were once novel are now commonplace. Buyers have seen it all. A buyer who would have gotten cold calls from 5 sellers per week in the early nineties, now gets 25 cold emails per day. Not only that, but there are only so many unique combinations of words, so that buyer has seen pretty close to every subject line, opening remark, demo, and pitch that could be conceived. Emails, LinkedIn messages, and other outreach mean very little as inboxes are flooded with good faith attempts at establishing relationships as well as mass-produced borderline spam that is completely irrelevant for the reader. These same buyers can sit through online demos, and product explainers long before ever engaging a seller. Regardless of the realities of solution comparisons, there is very little that will feel unique or differentiated to a buyer anymore.
There is an old saying that goes: “Bad sellers sell products, and good sellers sell solutions”. There is some merit to it, but it leaves us far short of understanding the actual mechanisms of sales. Sure, it is better to sell a solution to a problem than to sell the features of your product because buyers don’t care about features, they care about their problem and how it is solved. But the saying doesn’t go nearly far enough for two reasons.
First of all, there is a level beyond solutions, and that is outcomes. The buyer knowing the solution does not do the trick, they need to be shown the future state of the world, and how much better they will feel when they exist in that state compared to the status quo. You, as a seller, need to inspire emotion within the client that viscerally reminds them about their disdain for the status quo, and about their hopefulness for their desired outcome. This is not a logical process; it is an emotional one. It’s not about differentiators and solutions, it’s about problems, feelings, and desired outcomes.
But secondly, and perhaps more importantly, selling solutions, or even outcomes, just won’t have any impact on the buyer unless they believe in what the seller is telling them, and they won’t. You are no different from everyone else who walks into their office, you didn’t earn a right to be there, and your credibility is limited and certainly no better than your competitors. So the buyer has no reason to trust your assessment of your solution. The only way that you can sell your solution and your outcome is if you first jolt your client into a state where they are receptive to something new, and do a good enough job of selling yourself to convince that client that you have credibility and that they can rely on what you say. The only way to do that is to add value to the conversation and focus on the problems and the outcomes. Any focus on the solution itself, prior to establishing credibility, will just remind the client of your bias. Conversations about problems, the industry, and the clients desired outcomes help them understand what they need absent of their feelings of seller bias.
Inspiring negative client emotion around their problem, and positive client emotion around a desired outcome, as well as adding value and establishing credibility are both hard things to do, but they are eminently doable.
Dan Greenberg · February 22, 2024 · 8 min read
Let’s start with the “hate” side first and get it out of the way.
Sales and sales adjacent roles can be frustrating. Sellers can be mired in uncertainty and reliance on others. They are constantly judged by numbers to the exclusion of all else. They have their comp plans changed at the whim of management. And, the expectations are relentless; every month or quarter brings new and aggressive goals and the ever-present question from leadership, “what have you done for me lately”? In fairness, you probably understood the “hate” side intuitively. It’s not hard to find people who are not in sales who profess their never-ending commitment to never end up in sales. More to the point, it is not hard to find salespeople who spend the majority of their time worrying and complaining about the things that make their job so tough. There are myriads of social media accounts with millions of followers just churning out memes and comments about how frustrating sales is.
The “love” part may be a bit less obvious.
Sales is a competitive endeavor that invites those who want to work hard and develop skills to learn incredible amounts. It allows you to make a lot of money without spending years in school learning a specific trade or technical skill set. It allows you to get ahead in the business world, and gain influence throughout your career.
But I want to go a bit deeper and talk about the things that sales can teach a person that go beyond corporate success. Improving persuasion skills and behaviors not only makes you better at sales, it can make you better at life. I don’t only mean better at life, as in, more likely to get your way, although that may be true. I mean that the attunement, and perceptiveness that good sellers learn can make you a better person. This is a pretty lofty claim, but it is worth considering. Quite simply put, sales has taught me to be a better person.
Active Listening:
Sales, and development of sales skills has made me a better listener. I started as a pretty bad listener, and I am still not great, but active listening is a skill that must be nurtured and developed. Human beings cannot actually multitask in the sense that our active brain is always only focused on one thing, so if we are trying to listen to a person talk, and we are simultaneously doing something else or thinking about something else, we will not take in the information that person is conveying. Sales encompasses a consistent set of social and business interactions that, taken together, can help complete a puzzle explaining what the client really needs and wants. These social and business interactions are shrouded in political opaqueness, self-interested modification and curation of information, and posturing and power dynamics that distort and hide what is important. Any of the important signals that a seller needs to pick up on can be missed if the seller is distracted even in the slightest. It is so easy to get distracted by other screens and devices, and even just by other thoughts. Training yourself to actively listen is a sales behavior that is unparalleled in importance but can be so beneficial to so many other parts of a person’s life.
Empathy:
Sales learning and training has also undoubtedly made me a more empathetic person, who is more able to understand the perspectives of others. We often find sellers who talk about how a client of theirs is “an idiot” or “incompetent”, or a “jerk” or any one of a number of other reasons why the deal may not be moving forward. Although there are clients out there who are idiots, and incompetents, and jerks, the most common reason why a deal is stalled, or stalling, is that incentives are not aligned. While it is certainly fun, and healthy sometimes, to joke about the deficiencies of clients, sellers who think about client incentives will be systematically more successful at closing deals than those who blame stumbling blocks on the clients themselves. This idea does not only go for sales, it goes for almost any encounter in life, and proactively cultivating a greater ability to default to understanding perspectives instead of blaming the other side is a life skill much more so than a sales skill.
Balance:
In sales, you can close a massive deal on September 30th that makes your quarter, and you can subsequently endure 2 months of mishaps and unforeseen complications that make your next quarter’s goal feel unattainable. That feeling of elation and pride at the end of the past quarter can change into hopelessness, and frustration so quickly. Others experience these highs and lows in a more muted way, but sellers live and die by them, metaphorically, of course, because they are judged and compensated almost completely based on numbers. The experience that a seller gains from going through this tumultuous existence is incredibly educational. Spending a lot of time celebrating a win and replaying it over and over in your head, while assuming that you were completely responsible for it and that you can repeat it almost at will, will only serve to distract you from the mundane tasks that are required to get the next win. Similarly, brooding and feeling sorry for yourself after a loss or dry spell, and constantly thinking about all of the ‘what if’s that could have changed it, while assuming that uncontrollable external factors doomed the deal, will only serve to give off an air of desperation and prevent you from focusing on the next win. Sellers who deal with the constant ups and downs of sales are better able to be balanced emotionally and intellectually so that they can focus on the next task at hand. This is a very important life skill, not just a sales skill.
Follow Through:
Follow through is sorely missing in so many of our business and social interactions. This is so much so that we needed to invent a new term, “ghosting”, to describe the proliferation of people who could not even follow through enough to notify the other human being that they, in fact, would not be following through. In addition to follow through being important to the moral fabric of our society, sales processes have a certain level of momentum to them. If a deal sits in a holding pattern for long enough, it will become stale. This is because the buyer will develop an expectation that the deal will not close. This will lead them to justify the lack of need for the solution, and likely to develop contingencies that replace the solution. As sellers experience deal cycles and start to recognize patterns where deals that sit dormant almost never close, they develop stronger follow up impulses and skills, which in turn, are good for social interactions.
The business and the function of sales is to make money, but what you take away from it as a person, and how it improves other aspects of your life is what I love about sales.
Gordon Gekko was a little bit right, but mostly wrong, when he said, “Greed is good”. Greed is good only in so much as it is a measurable constant that we can use to understand motivation. But it must be balanced by something. Greed and personal incentives are an undeniable, and ever-present part of our world, but must be balanced by individual choices. Selfish incentives are understandable, and they give us a framework in which to make decisions and set rules. The rules are there to protect against those who would take advantage of others, and to define the boundaries of socially acceptable conduct. They are not there to define each individual’s moral feelings and guidelines.
Why am I suddenly getting all philosophical? It is not because I am turning this into a philosophy or morality blog. We often find that people tend to create a dichotomy between moral behavior and smart business decisions. They pit the two against each other, but this is a false dichotomy. The skills and impulses that we look to develop as sellers make us more attentive and perceptive. They make us better listeners. They make us better teachers. And, they make us better able to understand people sitting across the table from us.
I am not looking through rose-colored glasses when I tell you that making money and treating people the right way don’t have to butt heads. Each person has to define their own moral guidelines and decide what is acceptable for them and what is not. But well within the boundaries of socially acceptable behavior is a wide array of skills, strategies, and actions that can be taken to optimize sales success and pursue opportunity and money. The best sellers establish relationships based on respect, and don’t spend time trying to employ less than reputable tactics to close deals that are not meant to be. Those deals are a waste of their time because there are always other, better deals out there, that don’t call for lies and deception. The business and the function of sales is to make money, but how you treat the people you interact with is truly important.
Dan Greenberg · February 8, 2024 · 6 min read
Many traditional sales managers will push the message that sales is a numbers game. While there is some truth to that, and even low skilled sellers can have some success if the numbers are high enough, the sentiment is detrimental to the development of sales skill.
Sure, you need enough leads and opportunities to hit your goal. Most suspects don’t turn into prospects. Most prospects don’t turn into leads. Most leads don’t turn into opportunities. And, most opportunities don’t turn into deals. You need to have enough in your pipeline to make the math work. You also need enough in your pipeline that you are not worried about losing a deal. If you are too worried about one single deal, you will act needy, which will cause you to make bad decisions, and worse, if a buyer senses your neediness, they will run for the hills.
But once you have satisfied the basic numbers requirement, adequately filling your pipeline, and you have a process in place to maintain that pipeline and keep it full, sales becomes about skill. The difference between converting two percent of your leads into deals, and four percent of your leads into deals is 2X. That means two times more goal achievement and two times more commission. Finding an additional two percent is not easy, but it is very doable, and it takes skill and development. If you are focused on sales being a numbers game, then you are less likely to develop the skills needed to increase your win rate.
Your time is finite and valuable, while your quality improvements are force multipliers. If your pipeline has 200 leads in it, and you want to double your success, you will have to get to 400 leads if your focus is on numbers alone. That will mean doubling your time and effort. However, if you invest the resources and time now, and improve your sales skills, in the long run, you can learn to close 8 out of 200 leads instead of 4, and you will be spending a similar amount of time as before, but making twice as much money. I find it hard to imagine that if you can close 4 out of 200 deals, that you could not improve your skills and find 8 that can close.
The skills? Well, most of the articles that I post talk about those specific skills. Basically, they boil down to understanding needs, defining problems in your buyer’s terms, understanding how businesses work, speaking about outcomes and value in a challenging but productive way, controlling meetings, and writing and speaking in a simple and understandable manner. As you become more of a master in those skills, you should be able to sniff out, early in your process, that 100 of those 200 leads are not worth your time, which means two very important things. The first is obvious, don’t waste your time on those 100 that are not worth your time. The second is where we shift modes slightly…
The second is that you no longer have 200 leads in your pipeline, you now have only 100 leads. In addition to working the good 100, it is your job to fill up your pipeline and replace the bad 100. The easiest thing to do is to focus only on your current leads and deals, and forget to refill your pipeline. It is easy to do and easy to justify, but it is the worst thing you can do. As soon as your pipeline suffers, your deal making ability will suffer. You can improve every skill in your arsenal, and bring up your win ratio up, but if the pipeline isn’t there, the math won’t work.
If you have been paying attention, the article just shifted pretty significantly and this second half seems to contradict the first half. Afterall, if sales is about skill, and win rate, why should I focus on filling my pipeline? Sellers need to balance two truths in their mind quite often, just as many people need to do in life to be successful. There is a great line from the movie, The Secret Life of Walter Mitty. When challenged about a decision he made, Walter dryly responds “…it was a necessity and a mistake”. In other words, in life, we often have trade offs. Sometimes we have two bad options, but it’s usually better to take one than to be indecisive. Sometimes we have two things that need to be done, and although one may be less desirable and may even inhibit us in the short run, it still may be the right decision for the long run.
Organize your book of business like a business owner. Create processes and routines for yourself, and stick to the routines you build. If you don’t create routines, it will be easy to justify doing the things you want to do, while forgetting about the things you need to do.
The 80/20 rule is well documented and can be seen in many areas of business and life. Simply put, it explains that about 80 percent of the output often comes from about 20 percent of the input. In sales, this would mean that 80% of your revenue will come from 20% of your clients. It is not a hard and fast rule, and the exact numbers can vary, but it can be observed quite often. Jan-Benedict Steenkamp, a marketing professor at the University of North Carolina at Chapel Hill looked at numbers for sales and determined that in certain sales environments 20% of the customers account for about 60% of revenue. Regardless of the exact numbers, the fact is that identifying the customers that are the most likely to buy and the most likely to spend a lot is a major portion of your job. The key is not only understanding who to spend your time with, but also understanding who NOT to spend your time with, and how to build a repeatable, and actionable process for replacing them in your pipeline.
The takeaway is that sales is both a numbers game and a win-rate game. People who try to tell you that it is one or the other are oversimplifying it.
Win Rate:
Numbers:
Dan Greenberg · January 24, 2024 · 8 min read
There is no perfect cold email, or cold call script that will make everything magically fall into place. Sales takes routine and hard work, and a willingness to accept rejection. There are people out there who are incredibly disciplined and have trained themselves to live in a world of consistent optimism and hope, but that’s just not me, and I suspect it’s not most of you either. Frustration is okay, occasional sulking is even okay. What is important is routine, and the ability to recover and get back to your routine.
Getting attention is hard because, by definition, a person who does not know you, has no drive or incentive to spend resources like time and money listening to you or buying from you. Buyers are bombarded by outreach, and completely jaded, so outreach must be systematic, and intelligent. It must speak directly to the buyer and ask them for just a bit of their attention.
There are two types of outreach, ‘outreach for now’, and ‘outreach for later’. Both are vital, and without either one, you will struggle as a seller.
‘Outreach for now’ is a set of activities that drive conversations and relationships that can potentially convert in the short run. Since most marketing tactics, and cold outreach generally take a long time to come to fruition, your bag of tricks for this bucket is relatively limited, and scale will be very low. However, the relationships that you put in your pipeline form this activity are the most likely to convert and will have the shortest sales cycle. The tools you have in your toolkit for this type of outreach are generally your own network and referrals. We spent some time focusing on referrals in this blog at the end of last year, so we will focus more on the ‘outreach for later’ bucket in this article.
‘Outreach for later’ is a set of activities that are meant to build your pipeline 4 to 6 months from now. These activities include research, sales intelligence tools, marketing messaging, and cold outreach. With these methods, you have the ability to research in bulk and send campaign based, although targeted and relevant messages to scalable groups of prospects. This approach, for the most part, will benefit your book of business 4–6 months down the road. In other words, if you are reading this in mid-January, and you don’t start researching and targeting cold outreach now, you will likely have a bad May, June, and July.
Clients don’t often, respond to the first message, or the second, or the third, or the fourth. I could go on. This is because there are a few barriers that ‘outreach for later’ has to break through before any prospect can rise to the level of potential that is worth your time. Your goal with cold outreach is not to convince the prospect to buy. You can’t. It will never happen. Your goal is to convince the prospect to invest just a little bit of time in you. That is all. Let me be clear, picking up a list and dialing for volume is not the answer. Buyers are skeptical, and jaded, and therefore cold outreach in the absence of research, targeted material, and inbound signals is a tremendous waste of time and a resource suck.
The story of Chet Holmes is well known in the sales literature world. It is the story of how Holmes was hired by Charlie Munger (Warren Buffett’s business partner) to head up a large and struggling sales organization. A couple of years in he was asked by Munger, “Are we lying, cheating, or stealing? I’ve never seen sales numbers this good”. The answer is that he was doing none of the above; he attributed his success to one important strategic decision. He had taken a list of 2,000 prospects, trimmed it to the 167 best potential clients and focused 100% of his team’s energy on those 167 clients.
This story is well known, and not new, but it teaches us a very important lesson; 10 well informed, targeted, tailored outreaches are better than 100 ‘spray and pray’ outreaches. The time that you spend on cold outreach should not be spent on volume and tallying as many calls and messages as possible, it should be spent on research, tailoring of information, and crafting of messages that fit. The messages don’t have to be witty or perfect, they just need to speak directly to the person you are speaking to.
Many sellers are scared by this idea. They think to themselves; “what if I focus my list but accidentally leave off potential clients who really were interested and now will never buy from me?” Sure, this is a slight risk, but the real calculation is the value of all of the lost time that you will spend reaching out to clients that will be wasted because your messages are not targeted and don’t elicit a response. You are not a call center.
You are an executive, and your job is to solve problems for specific clients that you select, and that are worthy of the time you will spend on them.
Once you have wrapped your mind around that idea, it is time to set a routine. Resilience is not some magical phenomenon or idea that is fundamentally built into the personality of good sellers by nature. Resilience is simply the setting of routines and the discipline to adhere to those routines without succumbing to the desire to avoid them.
The world has changed, we have more technology, and we can use that technology to make our jobs more enjoyable and more fruitful. Information allows us to research, tools allow us to target, tailor, and gauge inbound interest, and platforms allow us to communicate in more effective ways than in the past. This means that instead of being a mindless drone and making the same phone call 100 times, you get to be an investigator for a while and figure out the best prospects. Then you get to be a researcher and learn about them and their companies. Then you get to be a marketer and tailor material that makes sense for each of them, and then you get to be a seller and send the messages and make the calls. Sure, you may not like every piece of the work, but it sure beats doing the same thing over and over again all day.
The key is to set time blocks and stick to them. Make sure that the time blocks make sense within the goals that you are trying to achieve, and that you are setting the right amount of time aside for the right activities. Treat your time blocks as commitments so that you are sure to do all of the activities in your control that lead to your success.
If you are in a more transactional role, you may pick 15 organizations with 2 people each, which will get you to 30 leads, or in a more strategic role, you may pick 5 organizations with 5 people each, which will get you to 25. Either way, you can do that research in about 90 minutes, and you can do the actual outreach in about an hour. Setting up time blocks accordingly will allow you to create a routine that is productive, and effective, but more importantly, doable. If you tell yourself you are going to research for 3 hours a day, and prospect for another 3, you may do it once or twice, but it is not sustainable. Build a routine that pushes you, but is sustainable. Something in the range of 2 hours a day is sustainable and something that you can hold yourself to task on without losing your mind.
Remember, the battle in outreach starts with visibility, moves to familiarity, and then to solution association. Your client needs to notice your outreach, then become familiar with you and your company, and then associate you and your company with the problem you solve. This can take months, and sometimes double-digit outreach attempts through multiple channels (phone, email, message). You can’t sell anything to anyone until they are receptive to listening, so all of the commercial teaching, discovery, presenting, social proof, and everything else that you have planned cannot start until you have overcome those three barriers.
Dan Greenberg · January 10, 2024 · 7 min read
How many times have you heard a sales manager ask about next steps? “What are the next steps?”, “Did you cover next steps?”, “Are there actionable next steps for this client?” You may even be the one asking that of people on your team or even of clients directly. Next steps are incredibly important because without them nothing that was accomplished in the meeting will be executed on. Yet, so often, next steps turn into a checklist item that is not at all related to actual progress.
All too often, Sellers talk about next steps in their own terms and not in the client’s terms. This may be because they are anticipating the questions that they will get from their manager. “When is the next meeting?”, “What is the expected close date?” But clients don’t care about meetings and close dates, so when a seller talks about next steps in terms of ‘follow up meetings’ and ‘close dates’, the client glazes over and stops being engaged with the process. If you are talking about next steps like this, you are not good at next steps. But don’t worry; it is not terminal. In fact, this is one of the easier fixes to make for a seller.
Next steps need to be in the buyer’s terms not yours. They need to establish the goal of that next interaction before ever scheduling it, and the goal needs to be related to the needs of the client. Buyers don’t want to get the sense that they are tools in your journey towards getting pen to paper. The reason why there should be, or will be another meeting is based on the client needs. The next meeting will happen because the client needs to learn something else, or the client needs to involve more internal people in the conversation, or the client needs to build a case or an understanding of the value of your solution relative to the cost. These are essentially the only three reasons for next steps. Any additional reasons for next steps are your reasons and must factor into your calculations but have no business as part of the conversation with the client.
Whether you are in a conversational setting or a more formal presentation setting, the next steps conversation should happen, but it will look different depending on that setting and your goals. If you are still in a heavy discovery phase, and need to learn about the client’s business, or get to know the client, or their business, or their process, it makes sense to plan for a conversational interaction. In these scenarios, you can frame the next steps conversation as a way for the client to learn more about others who have used your solutions and for you to understand their problem better so that you can help them build an understanding of the value and the likely outcomes. However, if your goals are more transactional, or your need is to position your solutions, or demo your product, or to instigate a negotiation, it will make sense to plan for a presentation or similar type of interaction. In these scenarios, you can frame the next steps as a way for your client learn more about the solutions so that they can start to think about the internal process and how they would like to position those internal conversations which will help them gather consensus.
Once you have decided on your goals, and how to frame the next steps conversation, you will have to execute that conversation in a way that keeps the client engaged, develops consensus on actionable and simple next steps, and motivates the client to take those simple actions.
Your job in this phase of the meeting is to tie the next interaction to a goal and a result that makes sense for the client so that they feel incentivized to make sure it happens and that it happens soon.
Dan Greenberg · December 14, 2023 · 8 min read
How many cold calls, messages, and emails is one referral worth? I wish I knew the exact answer to that question, but I don’t. What I do know is that the answer is ‘a lot’! Referrals are incredibly valuable and many many salespeople either don’t ask for them or don’t ask for them enough. I was guilty of this for most of my career. The reason why referrals are so valuable is that the first step with cold outreach is name recognition, followed by name / product association, followed by relevance level for the client. Not only do you get to skip all of those steps with a referral, you also get to skip the majority of the next few steps, which are proving thought leadership capabilities, and earning respect, and credibility.
If a buyer who is in a similar situation to the customer you are referred to makes an introduction, the new prospect will immediately assign you a level of credibility that would have likely taken months for you to earn otherwise. This is not only a huge time saver for salespeople, but in many situations, you may not have ever broken through all of those steps without the referral. This is juxtaposed to cold emails, cold messages, and cold calls, which have no magic formula, so it does not matter how good you are at formulating them, the overwhelming majority will get disregarded, rejected, or otherwise passed over.
There are essentially two ways to think about building your pipeline. There is one method that will pay immediate dividends, and one method that will pay long term dividends. The latter is research, sales intelligence tools, and cold outreach. With this method, you have the ability to research in bulk and send campaign based, although targeted and relevant messages to scalable groups of prospects. This approach, for the most part, will benefit your book of business 4–6 months down the road. In other words, if you are reading this in mid-December, and you don’t start researched and targeted cold outreach now, you will likely have a bad April, May, and June.
The other method is the one that pays more immediate dividends. It is less scalable, and more reliant on the sellers own network and capabilities, but it is much more effective, and much more efficient. This method is leveraging your own network, and asking for referrals. This method allows you to save time and be more effective in outreach. The problem with network leverage is that most sellers exhaust their own network pretty early in their tenure at a new company, so as far as this method is concerned we are left with referrals. Assuming that you can continue to grow your book of business, there will be a constantly evolving and growing base from which to ask for referrals, and one of the best things about referrals, as referenced above, is that they can have a positive impact on a book of business in the short run.
Who: As sellers, we should be thinking pretty consistently about where we should be mining for new referrals. We can, of course, ask existing clients for referrals. This makes a lot of sense because existing clients are likely to have some affinity towards your solution, and likely have contacts in similar industries where the solutions would have similar benefits. But there are a number of other potential breeding grounds for referrals that often get overlooked. Ask prospects for referrals. Don’t worry about losing a deal by asking your prospects who else you can help. Prospects who have recently said no, are generally more inclined to want to help, and prospects who are on the fence, who decide to refer you, will become more inclined to buy because they have created social pressure for themselves by tacitly vouching for you. It is also a good idea to think about internal channel partnership managers, marketing managers and product managers. They all have connections with counterparts and may be able to make warm introductions, especially the channel partnership managers whose job it is to create opportunities through partners.
Where / When: Asking for referrals is too often thought of as a stage in the sales process. It shouldn’t be. There is no need to wait until after the prospect says no, or until they become a client. It is important to be careful not to lead the prospect to believe that you are not focused on them, but in more social type settings, or at the end of calls, or in group meeting settings, it is often appropriate to ask prospects, clients, or partners who else they know that could benefit from a conversation. Making the ask seem like a very low lift is key. If you ask in a heavy or formal way, you will be sending a signal that this is a big ask and the responder will be less likely to comply. Conventions, conferences, and trade shows are another great place to ask for referrals. Attendees, even those who you do not yet work with, are in a networking mindset, and the ask will seem very appropriate.
Why: As we mentioned above, referrals are significantly more valuable, efficient, and more enjoyable to work than cold outreach. According to a Nielsen survey from 2012, 92% of consumers trust referrals from friends and family over other forms of advertising. Now, you may say that this is stated preferences, and that this is more of a B2C survey, and you would be right about both, but sales is a human to human endeavor. The individuals that you deal with want to find a reason, even a justification, to trust some person or product over others, and oftentimes this is very hard for them to parse without something to grasp onto. A referral can be just that piece of comfort that they are searching for. But if you need a little more help bridging the gap from B2C to B2B, according to a Blanc and Otus study, 86% of B2B buyers say word-of-mouth is the most influential factor in making purchase decisions. And, if you need one more stat to think about, an Influative study tells us that 84% of B2B decision makers start the buying process with a referral.
How: This only leaves us with the mechanics of the ask, which is, of course, a very important part. There are a few things to think about when asking for referrals. You should do it somewhat often, maybe two to four times a year with existing clients because their networks change, and they aren’t always thinking about everyone they know. Make sure to ask leading, but unobtrusive and lightweight questions when making the ask so that you make it easier for the prospect or client to think of the right person. Prompt them with the types of positions, or types of problems, or company names that will help them zero in on the right referrals, and then help them hone in on the right people as they answer your initial suggestions. It is also important to assure the potential referrer that you are going to have the right type of business conversation with their contact, so that they are not worried about you making them look bad. So, refer back to good conversations that you have had with the referrer and let them know that at the very least, it will be a good chance for their counterpart to learn a bit about the market, just as they have. Lastly, it is important to make the logistics as easy as possible for your potential referrer. If they have to send a message, offer to pre-write it for them, if they are having trouble thinking of the best way to make the connection, help them with the topics. And remember, you are in sales. Follow up will be key. This will not be at the top of their priority list, so make sure you are diligent about follow up.
Pipeline is key to any seller’s success. A seller must have options so that they don’t feel doomed if their next big potential deal falls through. Having only one, or a few deals in the pipeline will make a seller come off as needy, and it will limit their likelihood to close deals. Growing a pipeline is a consistent activity, and the best and most enjoyable leads over the course of time will come from referrals. According to the same Influitive study referenced above, 87% of B2B frontline sales personnel, 82% of sales leaders, and 78% of marketers believe that referrals are vital to sales success. They are right.
Dan Greenberg · November 21, 2023 · 7 min read
Most of us have heard a saying that goes something like, perfectionism is the enemy of success. I think many of us can intuitively understand it, but as with many sayings, even the ones that make the most sense, are hard to translate into practice in life, and even harder to translate into practice in a specific discipline. I think it’s important to look a bit deeper at what it means, and how it affects sales and sellers specifically.
We live in a world where access to data is seemingly endless, and yet, insights that can be gleaned from data are only slightly more available to us than before. Some of the reasons for this are related to limitations around tools and resources, but a much greater impact comes from humans’ limited capacity to synthesize and analyze real life occurrences due to the infinite number of variables. In other words, we can get better at gleaning insights from data over time, but there are limitations that will always cause there to be a gap between the amount of, and kind of data we can collect, versus what it can actually tell us.
And yet, business leaders still want to “wait for the study’”, “hold off until we see the report”, “delay until we get more information before making any decisions”. I understand this inclination, it’s human nature to want to gather as much information as possible before making a decision. And that can be a good thing. Making data driven decisions about how to approach problems is logical, but there are limitations. In this world of endless data that we live in, we expect that we can always get more data, and so we wait. We wait for all of the information, but at a certain point, more information cannot give you more insight into the right course of action. We wait for more information because we genuinely want to make good decisions, but we also do this out of fear. We think to ourselves, “Well, at least if I have all of the data, I can defend my decision, and then I won’t be blamed if it goes poorly”.
The problem with this approach is that when we wait too long, it becomes too late to make the right decision at the right time. When we wait too long to do something, either the decision gets made for us, or the decision becomes obvious because the situation has changed, and we missed the opportunity to make a decision when it mattered. Secretary of State from 2001 to 2005, Colin Powell, who was responsible for countless immensely consequential decisions developed what he called the 40–70 rule. He explained that with less than 40% of the information that you need to make a decision you are likely to make a poor decision, but that if you wait for more than 70% you will likely take too long, and the decision will be made for you.
What does all this have to do with sales and selling? Well known salesman, author, and motivational speaker Zig Ziglar famously said, “Anything worth doing, is worth doing poorly…until you can learn to do it well”. At first this may sound wrong to us. If it’s worth doing, just do it well, we might think. But what Ziglar was saying is very important. Before you learn to do something perfectly, before you have all the information you need; start doing it. Doing something is better than waiting. Sure, develop yourself, improve, get better over time, but don’t wait until you are there before starting.
I have witnessed many sellers over the course of my career say that they don’t want to waste their time making calls to clients if they aren’t sure those are the right clients and if they aren’t sure that the message is the right message. Heck, regrettably, I have been one of them. I’ve witnessed many managers and leaders holding off on sales efforts because they are waiting for an NPS survey, or market and competitive data that will help them understand how to sell and who to sell to. Thankfully, I don’t believe I have ever been in that group.
The amount of extra help that you can get from waiting for a bit more data, even a lot more data, is often negligible. It’s not that it can’t help at all, the problem is that the time you are spending waiting for data, you could be spending doing, and learning from that doing. It is much easier to make a decision, and implement it, and then iterate on it and make changes to that system than to try to improve on something that you have not put into action yet.
This is not an argument against the collection and analysis of data, in fact it is the opposite. The sooner you start doing, the more data you will have. Sure, you will make some mistakes in the beginning, but you would be surprised how many good conversations and relationships start from buyers informing sellers that they are thinking about something incorrectly. Rather than an argument against data collection and analysis, this is a call to shed two biases:
I’ll leave you with a quote from writer / journalist Carolyn Gregoire: “The great irony of Perfectionism is that while it is characterized by an intense desire to succeed, it can be the very thing that prevents success. Perfectionism is highly correlated with fear of failure, which is generally not the best motivator, {it is also associated with} self-defeating behavior such as procrastination”.
Yes, there are times in life when perfectionism is beneficial to the moment, and to the task at hand, but like most things, it is situational. Building a machine that will create a component for the space shuttle demands perfectionism. In sales, on the other hand, perfectionism is rarely the answer, mostly because we are dealing with unpredictable humans and situations with so many variables that there is no formula for getting it right every time, so the best bet is to do the opposite. Get it wrong. I don’t mean on purpose, but act. Do it a lot, and get it wrong sometimes, and then get better over time.
Dan Greenberg · November 1, 2023 · 6 min read
A friend of mine started a new job in sales. It’s her first job in sales. She has raised money for nonprofits in the past and the new job is selling SaaS tools to nonprofits, so it is not out of the blue for her, but nonetheless, it’s very different, and something she has never done before.
During one of her early trainings, she was on a call with another new hire; a typically brash young seller, a year or two out of college. He proudly boasted to the group that on every single call that is answered, he starts with the line, “Do you have a minute, or should I just go jump off a cliff?” He swore by the line, said it works every time. I am not sure what his definition of “works” is, and beyond that, I am not sure how much of his statement was bravado, and confidence, and the desire to impart a sense to the group that he has it all figured out, but that was his claim, regardless.
My friend didn’t mention if the reactions were more eye rolls, or more agreement, but I would imagine that some people felt one way and some felt the other, regardless of how comfortable people felt expressing themselves.
My friend then commented to me that she would never use that line, because it wouldn’t sound like her personality and the buyer would see through it and hang up on her. I was, and am, in full agreement with her on that point, but the situation brings up an interesting consideration, and it launched us into a conversation about the comment and its goals.
The young, brash seller commented on his tactic and noted that it was a ‘pattern interrupter’, and that’s why it works. That’s the fancy sales training book name for what he did, anyway. He may have been simply speaking in shorthand, but his comment missed the point slightly. As it was relayed to me, his comments focused on the interruption as the virtuous component in the exchange but failed to inspect the role the buyer played in the exchange.
As sellers we sometimes think a lot about the things we say and the things we do, but we fail to think about the mindset of the buyer and how those things are received, and why.
As is the case with most buyers, in most situations, that buyer was likely focused on her job and things that were of immediate importance in the moment. She may have even been interested in what he was selling, but of course ‘not now’; ‘never now’. You can imagine the monologue of the subconscious part of the buyer’s brain going something like this, ‘I don’t have time for this now, after all, what I am doing right now is the most important thing, always. I, of all people, have made a proactive decision to do it, and I chose to do it in this moment, so why would I want to divert my attention to something else. What you are selling is a problem for later-me’.
It’s not that the buyer is proactively deciding to brush the seller off. Proactivity is solely devoted to the important tasks, and the buyer long ago entered a mode where her brain’s gatekeeper was given unlimited power to see off distraction, so the reaction to the sales call is a brush off, but it’s usually not a proactive one, it’s by rote.
“…Should I just jump off a cliff” is a little weird, maybe sleazy feeling, more importantly, it paints a certain picture of the seller in that initial first impression phase, and likely doesn’t lead to a lot of productive long-term relationships. That said, it is worth thinking about how you, as a seller, within your personality, break monotony, and get people out of their rote gatekeeper mode. It’s worth thinking about how you pull buyers back from that state of mind and jar them into a more proactive decision-making mode. You don’t have to shock them into a yes, it’s just a simple light nudge to remind them that they have the power, and their gatekeeper is not in charge anymore.
It’s worth experimenting with different tones, different lines, different openers, and different cadences, just to see what works. If you have the ability to break the monotony, you will put yourself in position to have significantly more substantive cold calls.
At this point in my articles, I often give suggestions around language that would help a reader translate the ideas into real world scenarios, but I am choosing not to do that in this article for two very simple reasons. One is that each person’s’ ‘monotony disruptors’ must be unique to their own personality, and two is that the best monotony disruptors are responses to the buyer’s initial rebuff and therefore must be a real time, unique response to a unique comment. The best way to improve this skill is to make a lot of cold calls, try a lot of new things, and leave inhibitions behind.
Breaking monotony is good for you, the seller. It helps you stay fresh and clear minded in a world that is governed by repetition, but as with most things, when we are able to take a step back and look at the situation from the other party’s perspective, we can see why breaking monotony is so important. We as humans are governed by routine, and that routine protects us from having to expend mental energy on the small disturbances that pop up consistently throughout the day. If you do not break the monotony for your buyer, you fade into the background as just another one of those minor disturbances. Your job is to consistently struggle to find new ways to break through those filters.
You don’t have to convince the buyer to buy. You don’t have to convince the buyer to think. You don’t even have to convince the buyer to listen to you. You just have to jar the buyer into the realization their brain is back in the driver seat.
Dan Greenberg · October 18, 2023 · 7 min read
There is a well-known dichotomy in academics and the professional world between scientific pursuits, and humanitarian, or social science based, or artistic pursuits. The arts are creative, and the sciences are technical. But where does that leave sellers? More than 10% of people in the United States are in sales or similar roles, and likely many more have sales responsibilities as part of the broader requirements for being successful at their job.
So where does the above leave us sellers and client success individuals? Are we technical or creative? Does it matter? I think it does, and for sellers who are successful, I believe that many fall decidedly on the creative side. They think about their job as a creative pursuit, and they recognize that falling into patterns and ruts can cause diminished success.
But what does it mean that sales is a creative pursuit. I don’t mean it in an abstract or fluffy way. I mean it in a very direct and applicable way. What I mean is that a seller’s job is to constantly craft and frame a story. While there are very technical and precise ways to so this, the realities of the real world, and human interaction mean that the situation and the inputs are constantly changing, and the only way to be relevant, and useful for the buyer in the moment is to be creative about how best to deliver and frame that story.
Ultimately, real creativity only shines on a foundation of technical excellence. We see this across disciplines. Wonderfully creative soccer or basketball players must have already mastered basic dribbling mechanics and team systems. Delightfully creative musicians and composers must have already mastered basic music fluency and instrumental expertise. And the list goes on. So it is for sellers; in order to be a creative and adaptive storyteller, one must first master the basics and the guidelines of good storytelling.
Beyond mastering the basics of storytelling, there is the simple matter that every company, every seller, every customer success person, must construct a story that can serve as the backbone for every single client interaction. There is a 30-second version of that story for an elevator pitch, a 10-minute version for a short conversation, a slide-based version for presentations, and even a product centric one for demos.
That’s right, even demos are stories. If you find yourself in a demo situation talking through solutions, features, ease of use, you are almost certainly making two mistakes at once; one is talking about too many things, and losing relevance for the customer, and the second is talking about solutions outside of the context of the problem, and therefore not grounding your explanations in usefulness for the client. Both mistakes lead to less engaged clients who are not in touch with their problems and the reasons they need you. Keep in mind that in a 10-minute intro meeting, the problem section will probably take up the majority of the time, while in a demo, the solution and resolution components will take up the lion’s share of the time. It’s not exactly the same story all the time, but it has the same foundation and components.
Now it’s time to think a bit about how that foundational story looks. There are multiple ways to write a foundational story that can be used across interactions, but I tend to think about it in four parts: introduction, problem, solution, resolution. This is not rocket-science, in fact, these are basic components that have been present in storytelling for centuries. The story has to be simple so that you can be creative and adapt when needed, and so that there is a clear and straight line from the beginning to the end that the client can follow.
What is in the Introduction Section: The introduction section must explain what you do, and why the conversation is taking place, not who you are. The client does not care about your awards and history. This section must explain what category you are in, and if you are better than others at what they need, or foundationally different than what is out there.
Goal of the Introduction Section: Your singular goal in the introduction section is to establish your right to be there. You must establish what you do in a way that tells the client that the rest of the conversation will be worth their time. The introduction is a sale within itself, and if the client buys what you are selling, they are committing to be engaged in the rest of the interaction. Do not move on from the introduction until you believe that the client is committed to do that.
What is in the Problem Section: The problem section must establish the fact that there is a problem that the client needs to solve or at least an opportunity for growth. This section must define the problem and the effects that the problem has on the broader business and the day-to-day interactions of your main decision makers.
Goal of the Problem Section: Your goal in the problem section is to establish and come to an agreement with the client on what the problem is and the effects that problem has on their business. However, more importantly, you must establish that the status quo is not sustainable and that the current solution, or lack of solution is not working. The status quo must be painted as the antagonist so that indecision cannot remain the comfortable fallback position. Do not move on from the problem conversation until you believe that the client is in agreement that the status quo is not a solution.
What is in the Solution Section: The solution section must pose a singular solution (not a list or a menu) to the client as a direct response to an agreed upon problem. This part of the interaction should not be about product or feature details, rather it should be about establishing a high-level understanding that if your solution meets the technical specs after evaluation, that it is conceptually the type of solution that will allow the client to overcome the problem.
Goal of the Solution Section: Your singular goal in the solution section is to establish a high-level understanding of the perceived value of your solution relative to the problem. It is very important that this conversation focuses on value and outcomes. In other words, before you move on, make sure that you and the client agree on the amount of value added to their business if you solution is implemented to solve their problem.
What is in the Resolution Section: The resolution section must cover technical aspects of your solution, ease of use and implementation, and allow the client to understand the costs of switching and costs of implementation in the context of the bigger problem that is being solved. Social proof is very important in this part of the interaction, which can be accomplished through talking about other relevant clients (Not a logo list) that have seen success and excelled through the your partnership with them.
Goal of the Resolution Section: The most important pieces to convey in the resolution section are the talking points and facts that allow your main point of contact to tell your story internally when you are no longer in the room. The resolution section is your support for the rest of the interaction and fills in all the details that were not crucial to the story as you went from introduction to problem to solution.
If you are not thinking about all your client interactions as chances to tell a story, you may be missing an opportunity to be creative and influential with your clients. Being relevant and useful is very important to your interactions, and the creativity needed to excel in those tasks can only be accessed consistently when grounded in the foundation of good storytelling technique.
Dan Greenberg · October 4, 2023 · 8 min read
Every seller who has spent a bit of time in the business has likely seen and used some kind of 4-quadrant decision matrix which classifies prospects in their pipeline as either large opportunities or small opportunities, as well as either ‘likely to close’ or ‘unlikely to close’. The idea is that you want to be spending your time on the deals that are going to net the most money, and on the ones that have the best chance to close. So, if we were to lay out all of the prospects as scatter plots on this matrix with four boxes, you would want to spend the most time with the ones that lie in the quadrant labeled ‘big opportunity’ and ‘likely to close’, and you would want to spend the least amount of time on the prospects labeled ‘small opportunity’ and ‘unlikely to close’.
All of this makes sense, right? Sure, it does. It is common sense, and it satisfies the sniff test, as well as some tougher scrutiny. But there is a problem. It only takes into account the high-level criteria. Specifically, it leaves out one very important sub-criterion, and that sub-criterion may be most important in evaluating both major criteria in the model.
Sales managers who ask their sellers to rank their deals in this way are not stupid, and it is not that they aren’t aware that there is nuance to the evaluations, but they are assuming, more hoping, that the sub-criterion is accounted for in the seller’s own evaluation of the ‘likelihood to close’. What I mean by this is that managers assume that sellers have a good understanding of all the factors that contribute to ‘likelihood to close’ and are able to make an accurate assessment of that likelihood, and that the assessment is independent of the ‘size of the opportunity’ assessment. They are assuming that this assessment by the seller factors in the company’s procurement process, its financials, the relationships with the broader prospect company, and the relationship with the individuals at the prospect company. It would be great if this were the case, but in reality, how often do deals that are classified as “high likelihood to close” sit in the pipeline for months and quarters on end without closing? The answer is: All the time. This happens much more often than would be expected given the percentage likelihood to close that sellers assign to their deals.
So, what is this magical sub-criterion that we aren’t spending enough time focusing on? It is the presence or absence of an effective internal champion. This factor is important enough to be evaluated on its own because there is no uniform procedure or expectation around how sellers evaluate their pipelines, so often the evaluations are based on perceived need, or perceived quality of the relationship between the seller and their main point of contact (POC). This is an especially troubling reality because perceived need is just that, perceived. And, more importantly, the quality of the relationship is often a negatively correlated data point, since individuals within buying organizations who take the time and effort to develop overly friendly social relationships with sellers are often the types of individuals who lack internal political influence, and the tools necessary to be an effective internal champion. This is exactly the reason why so many deals marked as “high likelihood to close” sit in the pipeline for much longer than a seller indicated was likely, and why so many never get pushed across the finish line.
The major problem with this is that if we are forecasting based on these seller-generated assumptions, and we are prioritizing our time, and our resources based on these evaluations, we will end up spending time, energy, and resources in places where it is not useful, while leaving other opportunities, with more potential, unattended.
It’s not that sellers and sales managers don’t think that individual relationships and internal champions are important, it is that most people simply do not know how to evaluate them. In their excellent book, “The Challenger Customer”, Brent Adamson and Matthew Dixon focus a great deal of time on defining what a potentially effective internal champion looks like, and perhaps more importantly, what ineffective internal POCs look like. These definitions can help sellers understand if they are in the right kind of prospect relationship to generate a truly effective internal champion that can keep up the momentum of their deal, even when they are not in the room. Adamson and Dixon define 6 types of employees within customer organizations to help think through the evaluation and actions that sellers can take when navigating prospect clients.
Here is my summary of what they say in their book: You must find the right partner inside the customer organization. This partner is the mobilizer. Star performers focus on finding change drivers and consensus builders and mostly forget about other traits. Top performing sellers make relationships with teachers (good), go-getters (good), and skeptics (good), while average sellers make relationships with guides (bad), friends (bad), and climbers (bad). This happens because great sellers know that those types of people are good at driving consensus and change. Average sellers just want relationships, and want to feel like they are making progress, and so they subconsciously seek relationships that are communicative and friendly, rather than ones that will drive deals forward. Teachers, go-getters, and skeptics are mobilizers. The others have no, or negative impact; they are the talkers.
Your mobilizers are your lynchpin, and they must be prompted to focus on the problem that is commercially relevant for your deal, and then given access to insights that help them form an opinion around solutions that they can then socialize amongst their team. These insights must be credible, relevant, and frame breaking. In other words, they must challenge the way the mobilizer and the rest of the company think about their problem and the current solutions, because if the problem is big enough, that means the current solutions are not working. The insights must challenge the status quo and must identify the current problems and status quo solutions as the enemy. Most importantly, the insights must be packaged in a way that drives your internal champion to want to convey the message and gather internal organizational support.
One of the most important things to understand is that if the main POC is not pushing back (skeptic), or building on the problem / insight productively (go-getter), or actively bringing others into the conversation (teacher), they are likely not an effective champion. Consistent availability (guide), agreeability (friend), and monopolized one-on-one interactions (climber) are not good things; they are signs that your POC is not an effective champion. Sellers get this backwards all the time. The relationships that are always easy and never challenging are the ones that rarely close. If you are talking about a commercial insight that you know means something to their business and the POC does not engage and challenge skeptically, there is a good chance they will not be an effective internal champion. It is important to test how individuals engage with you and others in their organization in order to understand if they are respected internally. Watch them interact with those in their organization or ask them to do a little homework. Effective mobilizers will do it if it’s the right task.
So, how do you know if you have a real champion who can effectively help move your deal towards the finish line?
And, how do you know if you have the wrong person, who will not help move your deal forward, and may even negatively impact it?
It is only once we incorporate thinking about internal effective champions, and the individual personal relationships that sellers have at prospect organizations that we can start to be able to make accurate evaluations of the likelihood to close, and of the size of opportunities. Until then, our 2-dimensional matrices will be logically sound, but largely, and misleadingly inaccurate.
Dan Greenberg · September 22, 2023 · 8 min read
Let’s be clear off the bat. There is no replacement for an in-person meeting. Body language queues, intimate interaction, and the social components of an in-person, face-to-face encounter, cannot be duplicated on a video call. However, the world has changed. Clients and partners are less willing to set up in-person meetings.
Organizations are less willing to set aside large travel and expense budgets, and certain mainstays of business relationships have just not resurfaced after the three-year hiatus that we took. Over time this could change, but in the meantime, as sellers, it is important that we take the time to improve our video conferencing skills and make sure that we are as effective as possible in these settings.
One-on-one video calls have their challenges, but the skill set that is needed to be effective on a one-on-one call is somewhat similar to the skill set that is needed to be effective on a phone call, which is something that most sellers have a lot of experience with. So, while there is a lot to be said on that matter, we should leave it for another day. Group video calls are another beast, and although there is some crossover with the skill set needed to be effective in an in-person group meeting, there are significant differences, and significant challenges when it comes to group video settings.
There is a funny thing about group interactions in business settings that most sellers have experienced, the more people that are present, the less likely you are to get a response. This is true for group emails, and slacks, and it is also a reality for group video calls. With the proliferation of video meetings, it seems like we should all spend a bit more time inspecting our Zoom/Teams/Google strategy and reflect a bit on how it is different and how it is similar to in person meetings, and what we should do to get the most out of these interactions.
Here are a few tips to make sure that you are really connecting with the people on your group meeting or demo, and ensuring that you are doing your part to be as effective as possible given the challenges presented by these settings:
At the end of any meeting it is important to recap, but it is especially so at the end of a video meeting. It is imperative to make sure that the level setting that you did early in the call is still valid and shared. Ask the individuals on the call to tell you their takeaways and ask them if they got everything out of the meeting that they needed to get out of it. It is important, as mentioned above, that your questions set the expectation that you want to hear from everyone, and that you facilitate that process by using people’s names and focusing on individuals in an organic and conversational way.
Teams, Google, Zoom, any demo or meeting that is not in person will present challenges, and none of the tips above are a silver bullet, but it is important to prepare with these ideas in mind so that you can do your part to make sure that your interactions are as effective as possible.
Dan Greenberg · September 6, 2023 · 6 min read
Speaking assumptively to clients and potential clients is good, but not really for the same reasons that many people think. If you have not spent a lot of time thinking through the mechanics of the reactions and responses to different types of speech, it is worthwhile to think about this one. As sellers, we come across situations many times a day in which we have to decide how to craft an email or respond to a question, and knowing why assumptiveness is good, can help us decide when to use it, and when to use another type of response.
The most common reasoning that you will hear as to why assumptive speech should not be used is that it is a form of soft pressure, a way to persuade someone who is leaning away from the decision we want them to make to change their mind. It can be seen as a “used-car salesman” tactic, a bit sleazy. People tend to push back on using assumptive phrases because they feel it is too forward and that it will make them uncomfortable to employ such a tactic. However, the human brain is not wired that way. Humans don’t perceive polite and confident assumptiveness as pushy or sleazy, but importantly, they do perceive lack of assumptiveness in a very negative light.
What we are discussing here is far different than pushiness or sleazy closing techniques. Sure, if a seller moves past assumptive, to pushy, or sleazy, this will likely have adverse effects on the deal process. If you were, in fact, a used-car salesman, and within 5 minutes of meeting a prospective buyer, you said something to the effect of, “Come on, I know you are already envisioning yourself driving down the highway in that car with the top down, now grab this pen and give me your John Hancock”, you would probably turn that buyer off and put yourself in a tough position that you could not recover from.
The assumptiveness I am referring to is a quiet, and calm confidence that leverages social proof, and tells the buyer that you expect them to be seriously considering your product because so many others already do.
This type of assumptive speech is not used to persuade the people that are leaning towards “no”. Rather, it is used to reassure those that are leaning towards “yes”. The biggest problem with lack of assumptiveness is that it is very likely to turn a person leaning towards “yes” into a “no”. Here is why: We speak assumptively because if the answer is “yes” or “leaning yes”, then speaking without being assumptive will implant doubt in the other party’s mind. They will think, “well if that guy isn’t sure, then maybe I shouldn’t be sure”. This is a mostly subconscious response. On the other hand, if the answer is “no”, or “leaning no”, speaking assumptively can, in some cases, slightly patronize the other party, but the damage it might do if executed tactfully is extremely minimal relative to the damage that can be done if we don’t speak assumptively.
We can learn something from reality TV shows like Survivor, and Big Brother. If you have ever watched these shows then you will know that whenever a player gets wind of another player who has been talking about voting them out, their first response is not, “Wow, I can’t believe they did that, I don’t like that person”. Their first response is almost always something along the lines of, “Wow, I thought that person trusted me and wanted to work with me”. You see, the response is not about reacting negatively to the other player, their brain has already made the leap past their feelings of ill will to the second level of analysis where they assume that because they were a target of the other person, that means that the other person, reflexively, does not trust them. In reality, being targeted by that person could have been for any one of a number of reasons, but sensing anything that conveys doubt from another person always implants doubt in the mind of the person doing the evaluating.
We see this same dynamic play out in the real world all the time, whether it is office politics, or international power struggles amongst dictators and military leaders. When person “A” shows that they are doubtful about an outcome, the response is almost always for person “B” to assume that person “A” lacks trust in the outcome being mutually pursued, and not to assume deferentialness, or politeness, or any other potential reasons for that doubtfulness. This, in turn, will make person “B” doubtful about the outcome, and more likely to back away. This is why assumptiveness is so important. Afterall, if I work for the company that is selling you a product, and I am doubtful that you will buy, even if you were leaning towards buying, that will send you a strong signal that maybe you should rethink your position.
It is important to be tactful, calm, and confident when employing assumptive speech, but assumptive speech is key in most sales settings, especially those where you believe the buyer is leaning towards a “yes”. It is also important to remember to leverage social proof as that always helps convey tactfulness and confidence. Here are a few examples that work well in emails, as well as conversationally:
Dan Greenberg · August 16, 2023 · 7 min read
The Dunning-Kruger Effect is a cognitive bias in which people with limited competence in a particular domain overestimate their abilities. Basically, the Dunning-Kruger Effect explains that when we are brand new at something, we are aware that we are not good at it, but as we start to get slightly more proficient at it, we quickly start to perceive our abilities to be much greater than they are until, eventually, we hit a roadblock and realize that we are not actually that good. Then, as we progress along the path of gaining expertise, our proficiency, and our confidence level start to align more properly.
In most professions, and with most skills and types of expertise, this holds true. It is partially where we get the idea of beginner’s luck from, and also why we come across people in conversation who tend to be overconfident in opinions when they are lacking expertise. You can see in the chart below that confidence peaks much too early in the proficiency process before correcting.
But there is one very relevant area where this does not hold true to the same extent as in most other areas, and that area is sales. Sellers who are new to the field tend to be under confident in their skills over long periods of time. They tend to overestimate the set of skills that they need in order to break into the field and achieve basic levels of proficiency.
It is estimated that about 1 out of every 9 people in the US is a salesperson of some kind, but in reality, most of us rely on sales heavily in our jobs and in our lives. Whether it is convincing your boss to adopt your initiative, or working with your team to help them buy into a process idea that you have, or even talking your husband or kids into the dinner place that you want to try. Sales, in one way or another, is a big part of almost all of our lives.
I was listening to an interview on the podcast “Planet Money” the other day. The interview was with PJ McGee who sells various items at county fairs. He is a veteran and well-respected salesperson amongst his peers. He answered one of the reporter’s questions by saying, “The most insulting thing we hear is when someone says, ‘you’re a natural born salesman’, well screw you, I spent a lot of time and effort, and a lot of energy to learn how to do this properly”.
What PJ is saying is that accomplished sellers who have developed their trade look at it as a craft. They hone their skills and improve gradually and significantly over time. They bristle at the idea that “sales is a numbers game”, because when you are good at your job it is about the skill and the processes that you develop over time. All of this is true, in order to be a highly productive salesperson, you must put in the work to develop your craft, and it will take time.
Fortunately for those who are just starting their journey as a salesperson, or even for those who have been selling for some time but have only recently committed to learning and building the skills necessary for long term success, and very fortunately for sales managers, the path is not linear.
If a person were to start learning a language, or a sport, or an instrument today, they would be pretty terrible at the skill on day one. I don’t know about most of you, but I don’t know how to play the piano, and if you asked me to sit down with an ensemble and start playing today, I might mash a few keys, and it would become evident within about six seconds that I have no business sitting down in front of the instrument with a group of professional musicians. This is the same for most skills; surgery, engineering, basketball, a new language.
However, it is not the case for sales. The reason is; and this is very important; sales effectiveness relies on three broad sets of traits; sales skills, hard work, and basic social skills.
The fact that hard work plays a central role in success and can be employed immediately is very important, and works hand-in-hand with the social acumen piece. I cannot just work really hard and therefore be a passable rocket scientist on day-one. But in sales, with basic social skills, I can blunt force my way to effective results in the early stages as I am improving my skill set.
There are not a lot of professions out there where reliance on social acuity is so integral as it is in sales. Basic skills, like listening, asking good questions, making others feel comfortable in your presence, and sensing emotions and feelings from others in the room are of paramount importance in sales. Most of us have been developing these skills since childhood, which means that we are not starting from zero when it comes to learning the craft of sales.
What you can see in the chart below is that in sales, as opposed to with other skills, we don’t start at zero when it comes to gaining proficiency. Yes. It takes just as long to master selling as it does with most other trades and crafts, but the starting point is different. And, we are often better at it, than our confidence level would suggest, especially early on in the journey.
It’s not really possible or necessary to quantify how far along the path to proficiency we all start when we set out to hone our sales skills, but what is most important is that we don’t forget about the basic social skills as we develop other complementary skills over time. I have seen countless salespeople start out as decent sellers, and as they feverishly work on improving themselves, they actually get worse over time in the early stages of development. The simple reason is that they forget to be human.
As developing sellers learn discovery skills, and presentation skills, they become robotic and start to worry about checking the boxes related to the skills they are learning, but in the process, they forget what is most important. You must sell yourself, otherwise you won’t have a chance of selling your product. The most likely buyers are the ones who trust their relationship with the seller, and a seller who loses touch with basic social skills will lose touch with their buyer.
The trick is to figure out how to improve at the advanced sales skills, while at the same time, not losing the basic human social skills that you have already developed just by being a person. One way to do that is to focus on perception and listening rather than talking and presenting. Here are a few thoughts on what I mean:
Dan Greenberg · August 2, 2023 · 6 min read
There are a lot of sales resources that talk about how important it is to tell a story with your presentations. People are more engaged by images and stories. Cavemen did not write bullet points on the walls of their caves; they told stories using pictures. We are also told that people identify with stories when they can see themselves as a participant, so it makes sense to build your story with the person you are trying to influence as the protagonist. All of this makes intuitive sense to us and so it has become sales dogma.
So, we all set out to build better presentations. We limit bullet points, we shorten slides, we create dynamic stories and incorporate images. We make our presentations customer centric and develop them around the buyer. Good…right?
Sure, that part is great. But we spend all that time developing a scenario where we make the buyer the hero… and then we start closing. We body slam that buyer with a barrage of information about how, magically, our product happens to solve all of their problems, and we basically insinuate that they would have to be an idiot not to agree that our product is the perfect solution. That’s not empowering. It systematically places the buyer in the beta role instead of the hero role.
STOP IT! DON’T SELL! DON’T CLOSE! It’s way too early for that. Plus, it was never about your solution in first place. It’s not even about their problem.
What we have done is taken away all agency and individual drive from the buyer. And by doing that we have taken away the incentive for them to want to collaborate with us on a decision.
We have left the buyer with two choices, the first choice the buyer has is to succumb to our barrage of information, which some may do by actually listening, but they will have no incentive to promote adoption after the meeting because they feel no ownership whatsoever. Others may succumb by shutting off their brains and tuning out so as not to waste any more mental energy. The other choice the buyer has is to recognize that they cannot add any value to the conversation in support of your solution, because you have rattled off a list of all of the benefits and positives. This causes them to start to think about reasons the product won’t work, since that is the only thought-provoking side of the conversation left. This inevitably leads to unnecessary, and emotionally entrenched objections.
Back in 2014 there was a show that aired called “Mind Games”. I highly recommend it for anyone interested in understanding human decision psychology. My appreciation for the show was clearly a minority opinion as it was dropped after 5 episodes, so I’ll forgive you if you’ve never heard of it. The show starred Steve Zahn as a behavioral psychology genius with social anxiety and other behavioral problems of his own. The co-star was Christian Slater, who played a possibly reforming former criminal, employed to help leverage his brother’s (Steve Zahn’s character) skills and keep his less helpful traits in check. Each of the episodes featured a “consulting” team who were hired to help influence an individual or group to do what a specific client wanted.
One of the episodes revolved around a client attempting to convince an insurance adjuster to cover an experimental procedure. Steve Zahn’s character recognized immediately that the adjuster did not have a lot of excitement in their life, and the opportunity to ‘make a difference’ was something that could be leveraged. He coached the client to probe and ask questions about other instances in the past where the adjuster had the opportunity to be a part of real change, or real progress, and to encourage the adjuster to talk about those instances and to describe what it would take to make this current issue a reality.
You see, the important thing is not the facts. It’s not the issue at hand, or the features of the product, or even the long-term benefits of the solution. The important thing is how an agreement will make the person on the other side of the table feel, more precisely, it is their perception of how it will make them feel. If you are discussing facts, and products, and solutions too much, you might not be bringing your client along for the emotional ride that they need to be on in order to WANT to reach an agreement.
Instead of only focusing on your solution and their needs, find ways to ask about their drive and desire to push internally to make a deal happen:
Let the buyer tell you the answers to these questions, because when they do, they will be painting a picture of big change in which they are the catalyst for that change. Let them develop a blueprint of themselves as the hero of the transformation, and then nurture that blueprint throughout the process. Once they have bought into the idea that you see them as a transformational leader, they will continue to make bold decisions and do bold things. They will not want to let you down. That’s how human psychology works.
Dan Greenberg · July 19, 2023 · 8 min read
You may have had the experience of being asked to “get to the demo” on a call or in a sales meeting.
This type of request, and other similar statements and comments, are meant to establish control and dominance over an interaction. Consciously or subconsciously the asker of the question is lining up the parameters of the meeting in a way that gives them the upper hand. It is a power play. It is meant to establish the asker as the “judge” and leader of the conversation, and to establish the responder as the one looking for approval from that “judge”.
There are other versions of this question, such as, “I have a hard stop in 20 minutes so you should get started”, or “I assume you brought slides to show us?”. Many sellers, trying to develop relationships, and conversational interactions experience these types of situations. What is important to grasp is what statements and questions like these can accomplish for the asker if YOU are not prepared to respond in the right way.
As mentioned above, the goal of these types of questions, whether the asker knows it consciously, or not, is to establish or gain power. The concept of power dynamics is quite hard to grasp and even harder to manipulate, so oftentimes, simple power plays can have a significant effect on a meeting because many people are not equipped to respond in a way that shifts that balance of power away from the original poser of the question. In these cases, if the seller submits and launches into a demo or pitch, the power dynamic is set by that simple power play early in the interaction and never gets reversed.
When a buyer says to you, “Just tell me about the features of your product” or “Give me a demo” or “OK, how much does it cost?”, your first reaction might be to think that these seem like normal questions, but these questions establish a frame in which you are presenting a response to a “judge” who is comparing you to others who have presented similarly. The asker of these questions is subtly, maybe even unconsciously, telling you that your job, as a seller, is to state your claim as to why your product is better than the competitors’ products, and then they, the asker, will process your information next to all the other information they already have and judge you against your competitors. You are one piece of a puzzle to them, no different than any other piece, and they are the “all-powerful judge” of your merit and likelihood of success. OK, sure, I am being a bit dramatic, but that doesn’t take away from the reality that this is how the power dynamics work.
In Oren Klaff’s very informative book “Pitch Anything” he asserts that any two individuals have perspectives, and often different perspectives. These perspectives govern how they each see a particular situation or thing. These perspectives, or frames cannot coexist because whoever’s frame of the situation is more persuasive, or powerful, will be used to discuss and evaluate the matter at the expense of the other frame. This is very important because it means that if you allow the customer’s “all-knowing judge” frame to persist, then you must adhere to being a single puzzle piece, no different than any of your competitors. That reality will give you very little ability to influence the ultimate outcome of the buying decision.
Any time you find yourself in a situation where you are being judged, you cannot win. Sure, if the other party was leaning towards buying, they may still do so, but you cannot improve your situation, you can only maintain the status quo. This is because those who put themselves in a place of judgement derive their power and control of a situation from the fact that they can identify issues and problems with what and who they are judging, namely you and your product. Identification of problems is what allows them to stay in their position of power. After all, if everything you said were to be right, and were to make sense, then who needs them? You become the hero, and they lose their power. This means that their incentive is to look for reasons to judge you and your product harshly.
So, it is imperative for you to change the frame in this situation. In order to do this, you must break their frame. You must change the situation so that you are not the one being judged, rather, you are the imparter of information that they cannot otherwise access. Better yet, you could even position yourself as the “judge” who decides if they are the right client for your solution or if your time is better spent elsewhere. Oftentimes you must do or say something unexpected in order to make that transition. This is why the worst thing you, as a seller, can do in this scenario is jump right into a presentation. Asking a seller to “just move on to the presentation”, or “show the slides” or “the demo” makes complete sense for the buyer. As soon as you are presenting, they are the “judge”, and have control over the situation. However, it makes no sense for the seller to acquiesce to the role of being judged.
This is a pivotal moment in any call or meeting. When the person across the table asks you to demo your product, explain your features or explain why you are the right vendor for them, you must derail their version of the process. Sure, you will answer their question, but you will do it in your own way and on your own terms. This must be professionally done and well executed, but you must interject in a way that wrestles control of the situation back from the other side of the table.
Simple questions that establish what the other person cares about in a solution, what they are currently missing, or what they need most, can help you shift the balance back to a focus on why they need you, and not, why you need them. Shifting this balance is important because if the potential buyer needs you, then logically, they are not the judge, which means they don’t control the power. These types of questions are hard to engineer because simply replying to a question about your product with a question about what is important to the asker can signal a resistance to share, or worse, that you just want to say exactly what the buyer wants to hear; so, it is important to flip the script in a subtle way. It is even important to remind the buyer that you know things that they don’t, like how their competitors are solving these problems, and how they are using tools similar to yours to make their lives easier. These reminders will legitimately move your customer to a position of need and start to wrestle control back to your side of the table.
The toughest part of derailing the asker’s process is the transition to your questions. Use things like social proof, examples, and insights, as well as occasional interjections to make the transition; here are some examples:
Remember, people value their time. They would not be meeting with you in the first place if they did not potentially need you. That makes it your job to figure out the buyer’s understanding of their need for your solutions, and what terms they use to describe that understanding. Then you can frame the entire call, or meeting around the words that they use to describe that need. Not your words and terms; theirs. That’s how you remind them of their need for you, which allows you to wrestle back control of the situation and ability to influence the outcome to your side of the table.
Dan Greenberg · July 5, 2023 · 7 min read
The “Uncanny Valley” theory suggests that humanoid objects that imperfectly resemble actual human beings provoke uncanny or strangely familiar feelings of uneasiness and revulsion in observers. Essentially what this means is that as robots appear more and more like humans, we evaluate them similarly to how we would evaluate a human. However, these robotic entities cannot quite ‘pull-off’ being a human, which elicits uneasy and strange feelings from the evaluator. On the other hand, when a robot entity is clearly a robot, that evaluation never takes place, so there is no apprehensive, uneasy feeling produced. This is relevant for us because sellers; who are almost exclusively humans…regardless of what others may think of them, run the risk of falling into a similar trap by robotically proceeding through preconceived conversation starters and discovery questions, rather than acting like real human beings and adding value to their conversations with customers. Adding value to a conversation is a simple social skill that we all do in our everyday social interactions.
I once had a sales manager who asked to join an in-person meeting of mine. This manager had never come to one of my meetings, so I did not know what to expect. He prepared a list of questions that he wanted to get answered by the client, which made sense. Some of the questions were overly simplistic, and some were overly technical, and we talked about how that would affect the conversation, but what we did not discuss was the structure and approach of the discovery session itself. The structure and approach was very influential in shaping the client’s feelings about us, and had a much more significant impact on the quality of the meeting than the content itself.
The meeting did not go well. We had a captive audience with the entire executive team of a fintech firm with money to spend, and we missed a big opportunity. This was about 13 years ago, and I was a much less experienced seller at the time, so I am by no means claiming that I would have ‘nailed it’ had I led the meeting. However, I knew in the moment that it wasn’t going well. I would even call part of the interaction cringeworthy, and it was pretty clear as to why. My sales manager had prepared a list of questions, and he went through the list in order, robotically, calling out that he had a list of questions and that he wanted to learn as much about them as possible. That was his singular task in that part of the meeting.
Bear with me here because this point is important in evaluating ourselves as sellers and sales teams. The problem was not the learning; customers want you to learn about them. The problem was not the questions; customers like to talk about themselves and answer questions. The problem was the long list of uninterrupted questions that were openly discussed as a way for us to gather as much information as possible. It was the approach a robot would take; singular focus on a goal to the exclusion of all else; until that goal is achieved. It lacked the human conversational quality of give and take. It made the evaluator uneasy.
I could feel the collective eye-rolls and sighs in the room. We had sucked the life out of the room, and we did it by leaching off of their knowledge through our questions without adding any value of our own. Why would that client ever need to, or want to talk to us in the future if all of the information and value-add was only headed in one direction; towards us.
Presentations are different than conversational meetings and they serve different functions. Presentations are one-way affairs. They are scripted and not meant to simulate or evoke feelings similar to social interactions. They are not conversational; they don’t reflect normal interpersonal behavior, and they are seen as such. However, as sellers try to turn meetings from presentations into conversations, they run the risk of getting close enough to normal interpersonal interaction without getting all the way there, and that makes them seem robotic. More precisely, this mis-step makes sellers seem like robots impersonating humans, trying to pull-off normal human interaction, and THAT is the Uncanny Value-Add Conundrum.
The most important part of a sales cycle is learning, but every time you ask a question, you capture value from the buyer without adding any to the conversation yourself. You must add value in order to be perceived as a true consultative resource for the client and gain the ability to influence the decision. So, how do you balance learning vs. adding value?
Asking questions and truly listening to answers is the most important part of every sale, but as a seller you have two jobs in the early stage of a sale. One is to ask questions, and truly listen to the answers, and the other is to sell yourself. You need to make sure that the buyer wants to talk to you, as a person. The buyer(s) must appreciate the value that YOU, as an individual, can add to the process. That is the only way that you will earn the right to truly be a valued consultant to the buyer and thus have the ability to influence the decision.
Discovery, as a phase in the sales cycle, is a misunderstood concept. As sellers we must be constantly learning, while at the same time adding value. If we are asking too much, we will be seen as leeches, not worth the buyer’s time. If we are adding too much value, we will be seen as pushing too hard, and not understanding the clients business well enough to give tailored advice and solutions, and in many cases they will be right.
It is not a seller’s job alone to add value. Companies as a whole must participate in this. The marketing team must provide insights that can be used in material and by sellers, and sales managers must discuss opportunities with their sellers to help tease out ideas and concepts that can be brought up in conversation with the client.
In their excellent book, “The Challenger Customer”, Brent Adamson and Matthew Dixon go to great lengths to describe the process and value of creating a “commercial insight” that can be used by marketing and sales teams to challenge their customers’ pre-conceived mental models. These “commercial insights” can be used to “confront” notions that often lead customers to default decisions like remaining with the status quo. Alternatively, these legacy notions can lead buying teams away from consensus decision making and into an antagonistic cycle that emphasises each internal individual’s issues with the deal. These cycles tend to lead to decisions that focus on lowest common denominators like price and ease of implementation, rather than the actual benefits of the solution and its potential value for the customer’s business. That can lead to suboptimal outcomes for your buyers and lost deals for you.
It is your job as a seller to prepare yourself to add value. To do this, you must think about the areas where you know more about the client’s business than even they do. At first, it may seem like this is not possible since they live and breathe their company. But you see things from an outsider’s perspective. You are more easily able to understand their competitors and the broader landscape, because you talk to those competitors. You also have the ability to see how companies in their space are using tools and products, like the ones you sell, to help themselves adapt, and grow, and even rethink well-established industry dogma. Lean on your marketing teams, and sales leadership to help define these insights, and come prepared to add value. Adding value makes you human, and gives you the permission you need to ask questions and learn everything that you need to know from the client in order to make the right deal for them and for you.
Dan Greenberg · June 22, 2023 · 5 min read
Why don’t men ask for directions? It’s a common joke, but it’s also a good question, and can provide some interesting insight into human decision making and buying decisions.
Of course, society is changing, and the ‘direction asking’ scenario arises much less often than it used to, especially with the advent of GPS in cars. However, I am guilty of this obtuse display of intellectual bravado, and we all have seen men, and yes, sometimes women, dispute the GPS system and go at it alone, against the better advise of the all knowing, slightly robotic voice calmly explaining the best route. Of course, we can’t live in alternate universes, so one who makes this decision is very rarely definitively proven right or wrong, but we can be relatively certain, on the whole, that the GPS system knows best…except, of course, in your case; that darn GPS just does not know all the tricks that you do.
Why does this happen? What is the incentive? Of course the person driving wants to get to the destination as soon as possible, and avoid traffic, there is no doubt about that. Any objective evaluation of the situation would tell you that a computer with millions of inputs and a satellite view of the whole route in front of you, has better information than you do with your limited information and 500 feet of viewable route.
So, the driver has a problem, and there is a clear solution. The problem is that the driver does not know the fastest route to the destination because of lack of information, and the solution is that the GPS does know the fastest route. So why are these drivers not buying the solution. After all, the cost is very low, basically free, and the resource cost is also low, the only incremental resource investment from the driver is listening to the calm robotic voice explaining the best route, right?
Seems simple. I have a problem; here is an easy solution at a low cost. Done deal.
But there is another step, and it is a crucial step, a step that almost every seller, even the best ones, don’t spend enough time and attention on. It is the step where the buyer’s perception of value is matched up with their perception of cost.
Notice, I used the word perception because the actual cost and value have no bearing on the outcome, only the buyer’s perception of the two. If we take some time to evaluate those two things, we may find a very different way of communicating with the buyer.
So, we ask ourselves, how does the buyer perceive cost, in addition to the obvious. There may be a perception that their authority, or knowledge or power, or value to the group, will be called into question if they have to rely on a calm and all-knowing robot to guide them through life. On the other hand, there may be a perception that if they offer a differing opinion than that all-knowing robot, and are proven right, they will experience the vindication and triumph of a king returning from a victorious battle. This is a value associated with a decision not to buy that we would have never detected without this analysis.
There is also likely a significant perceived cost associated with change in habit and routine. As humans, we are creatures of habit and we invest considerable energy into feeling comfortable with the routines that we set up for ourselves. Even something as seemingly innocuous as a new source of information is a significant change in habit and can cause discomfort with the potential new routine, as well as discomfort with the loss of the old routine; the status quo that we are invested in. This is a significant cost that would not have been uncovered without this analysis.
So how does this analysis help us sell? In this scenario, if the buyer were reminded that the likelihood of triumphant vindication over the robot is incredibly unlikely, and that the most likely alternative is inconclusiveness, or worse, a scenario where members of the group question the driver’s ‘clearly superior’ directional knowledge, the buyer may be helped to remember that the downside of disagreeing with the all-knowing robot may come with some shame and embarrassment, and that this scenario is more likely than the upside. In addition, conversations around how to build simple and satisfying routines and habits around the new solution might be a focus.
Notice, nowhere in the paragraph above were the benefits of the solution, or its low costs mentioned. We aren’t concerned with the solution, or even the problem. We are concerned with the buyer’s mental model of the world and how we can change that in a way that makes sense for the buyer, for us, and for the deal. This is a more nuanced understanding of the buyer’s decision making process that focuses itself on the things that the buyer rarely says out loud, but the very things that often get in the way of a deal.
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