The Bregman Leadership Podcast
Episode 68

Brent Adamson

The Challenger Sale

What is the secret to sales and marketing success? On this episode, I speak to Brent Adamson, co-author of The Challenger Sale. Brent and his colleague, Matthew Dixon, studied the data of thousands of salespeople and determined that one behavioral profile always outsells the rest: the Challenger. Discover what makes a Challenger-salesperson unique, why you should never “lead with” your value proposition, and the three traits you can train to help your team sell like Challengers.


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Book: The Challenger Sale


Peter: Welcome to the Bregman Leadership Podcast. I’m Peter Bregman, your host and CEO of Bregman Partners. This podcast is part of my mission to help you get massive traction on the things that matter most. We have with us today Brent Adamson. He wrote the book with Matt Dickson, The Challenger Sale: Taking Control of the Customer Conversation. He later also wrote the book, The Challenger Customer: Selling to the Hidden Influences Who Can Multiply Your Results.

I really enjoyed both of these books. I was schooled in consultative selling back when I was doing my initial consulting work in the, I hate to say it, late 80s, early 90s. This book was a refreshing take on that, and offered some data-based alternatives that have been very successful. We have Brent with us today. He is the managing director of CEB. CEB is the leading member based advisory company and it combines the best practices of thousands of member companies with advanced research methodologies and human capital analytics. They’ve look at, And we’ll ask Brent to describe this for us, a lot of research on what distinguishes the best sales people from good sales people and working to replicate those techniques and advantages in our broader sales forces. So, Brent, Welcome to the Bregman Leadership Podcast.

Brent: Thanks, Peter. It’s great to be with you.

Peter: Brent, what is the challenger sale? How does it differ from the typical sales process used to people might be used to?

Brent: Well, let me just dive in on. I’ll start in Peter and then stop me wherever it seems best because there’s a number of different ways to come at that question that I think are all hopefully interesting. But the, by way of this brief background, I sit in the sales and marketing practice at CEB. We work with every major industry geography good at market model across the business-to-business sales. We work at heads of sales in our teams around the world, just trying to understand through a lot of research, a lot of data, a lot analysis, quantitative, qualitative work, just what does world-class selling and, for that matter, marketing look like when engaged in a complex business-to-business sale? Whether it’s business services, products, you name it. What’s interesting, Peter … So the story in it in a lot of ways for the challenger’s sales starts back in 2009 or so.

Do you remember 2009? It was tough selling back in 2009, 2010, where, as we worked with our heads of sales members around the world, the one thing that we knew everyone was doing was struggling, of course. Because, it was the down economy, everything had gone off a cliff. It wasn’t so much that we weren’t selling as much as customers weren’t buying, so everyone was on the sidelines. You know, you look at individual sales rep, they’re all at 30, 40% of goal, if that. It was a tough year, and tough couple of years. The thing that was so interesting about that time from our perspective as a research organization, as organization helping companies make progress and selling challenging, wasn’t so much that every sales rep was at 40% at of goal.

It was that, there was every sales leader we talked, every chief sales officer we were on the phone with back then, almost, always inevitably said the same thing. They said, “You know, my whole team is really struggling except for this one guy.” Right? So virtually everyone had this one person, this man or woman, this rep that the sales professional out there who was not at 40% at goal but it, a 140% at goal. Okay, within what was arguably one of the worst economies in recent memory, if arguably not ever.

That led to this really interesting question. If there was ever a time when there was a clear difference between star performing sales professionals and everyone else, it was then and it lead us to this sort of go after this question, what in the world were these individuals doing that is so different, and could we figure that out in terms of behavior skills, knowledge, attitudes. Could we use data analysis that try and pin that down. And then more importantly, if we could figure that out, could we somehow bottle that and export it to everyone else around the world, across the core performers at most of our organization.

That’s the back story that led us on challenger, down the challenger path. Where we went out originally studied about 6,000 sales reps were now over, well over a 100,000 sales professionals in our database. It led to a number of really interesting conclusions. In some ways, Peter, that’s the … There’s a different back story to this which is sort of what we’re all doing in sales and how sales organizations operate, but that’s sort of the research methodology backstory of how we stumbled upon the story in the first place. So-

Peter: And distinguishing, just to be clear, so distinguishing between a great sales person and an average sales person is a very hard number, which is the amount of sales they make in a given period.

Brent: Yes, so for us, that’s a great question because, it’s a usually this sort of gets buried in the research somewhere. When we define a star performing sales rep, what we mean by that is someone who is able and [inaudible 00:05:11] someone who is consistently met or exceeded goal, quarter over quarter for a number of years. Different way to think about it, is someone who cam consistently drive growth in their sales territory. Whether they’re hunting or farming, that, this question inevitably comes up. It doesn’t matter. This work applies equally well to someone going out looking to acquire new logos or someone farming in the as it were, farming in a existing account. It’s someone who is able to expand their book of business and drive that kind of growth. That’s what were looking for. That’s why I can tell you what we found. Does that make sense?

Peter: Yup, absolutely.

Brent: All right, here’s what we found in a nutshell that we can dive in deeper, the backstory of why we think we found it, which is, I think inarguably, in some ways arguably and more interesting perspective. But what we found is, so once we gather all these datas. We went on and tested. This is a range of different behaviors, skills, knowledge, attitudes, the types of things that a sales rep engages in to do their job. Now you got like what 55 or so attributes, you got thousands thousands sales reps. We had to make some sense out of that database. We ran what’s called a factor analysis on that database, which is simply just a means to take a big set of data, boil it down to a small number of manageable categories, where everything in that category moves together in a statistically significant way. That’s a lot of mumbo jumbo, I know.

Basically what happened was, when we ran this analysis, we found out virtually every sales professional has this tendency to fall into one of five distinct profiles. There’s these five profiles of sales reps. Now, they’re not mutually exclusive. It’s not like, you’re all of one and none of the other four, there’s some overlap, which you find is you might be a little bit of one, a little bit of another. Everyone has sort of a baseline level of performance across a lot of the attributes in many of the profiles.

But all of that said, we nonetheless found that virtually every sales professional that we’ve studied around the world has this tendency to gravitate to the behaviors defining one of these five profiles as sort of their primary posture when facing off with customers. What I thought, I did … You could imagine one of these profiles being this quote un-quote, challenger, and they’re most likely to win. Let me take a minute, Peter if it’s okay, I’ll run you through the five profiles very briefly. Then, tell you what I found, that sounds okay?

Peter: Yeah, sure. Let’s go kind of fast on that because I want to dive in more deeply to the challenger.

Brent: Very good. It’s kind of a quick punchline. What we found is there’s this hard worker profile. Someone who’s always willing to go the extra mile, doesn’t give up easily, you know. Shows up early, stays late. More calls in an hour, more visits per week. They love feedback, so that’s the hard worker.

The challenger is the sort of the debater on the team. The challenger rep, they’ve got this very deep knowledge of the customer’s business but they use that to challenge the customer’s thinking. Not about us, not about what we do, but challenges the customer themselves and what they’re doing. Kinda push the customer out of their comfort zone a little bit.

The third is what we call the relationship builder. Now, the relationship builder is interesting because they’re typically focused on building personal and professional relationships and advocates across the customer organization. They’re very generous with their time, their primary posture is largely, whatever you need, I am here for you. You say the word, and I will get it done.

The fourth is, what we call the lone wolf. The lone wolf is sort of that prima donna of your sales organization. They’re the ones that drive you crazy because they follow their own instincts instead of the rules. There’s no trip reports, there’s no CRM entries and frankly, you’d fire them if you could but you can’t because well, because they’re always crushing their number. Its always really the question what you do with your lone wolves.

Then finally is the problem solver. The problem solver is very detail oriented, they’re very focused on making sure that all the promises that are inevitably made as part of a sale, get kept once that sale was done. They got this very strong post sales implementation focus.

Now, it’s interesting that once we find this five profiles, the next thing that we naturally did is compare them to performance. What we found is two things that were really interesting. One is, that of those five, by far the most, the profile most likely to be a star performer is in fact this challenger Rep. The one that’s out challenging customer’s think differently about their business. I think equally and interestingly, we can dig in Peter there, if you want, is that the rep least likely to be a star performer was in fact the relationship builder. Which was very interesting for most of our heads of sales members because they would tell you in many ways, they place their biggest bet on the profile least likely to win, because they’ve been focused on building these service oriented relationships with customers where the primary posture is, again, “Whatever you need, we are here for you. We want to be your partner in whatever you’ve gotta get done.” That’s the punchline. We can dig in wherever you want.

Peter: Yeah and I think actually, I mean, I could make a case for anyone of these. Like the hard worker, certainly if they’re working on the wrong stuff, wouldn’t work. But you would certainly want a hard worker who is doing, putting in the extra hours in order to persist in making the sale. The relationship builder, everyone’s always thought of the relationship builder as a common trait of really powerful sales people. Lone wolf there, I’ve seen a psychometric research that’s sales people tend to be lone wolves.

You’ve said that it’s not just one or the other, people have an element of each of these, but if I were to guess, I would have said the challenger from a sales perspective would be the least likely to be effective sales, because sales people, I think often try to make people feel good. There’s something about the challenger of all of these who is actually not out there to make the person feel good. In fact, what you’re saying is, the challenger, the star performer is out there to make their prospects feel uncomfortable and feel less good, and there’s something counter-intuitive about that. Meaning, I don’t know that I want to do business with someone who makes me feel bad. Can you explain that?

Brent: Yeah, Absolutely. One thing could we have to be super careful on because, by the way, we chose this language in someways to be intentionally, if not provocative, then at least thought provoking. Right. The … couple of thoughts. One is, when we find that these relationship builders least likely to win. One of the things we definitively know, we all know intuitively from sales is that, I think we’d all agree, of course, relationships are hugely important in sales. It’s not that relationships don’t matter.

But the question does become, What is the heart and soul? What is the basis of their relationships where we seem to build with our customers? Is that largely just familiarity? Is it largely just, hey we know this guy so we’ll buy from him because we’re finding today is customers don’t buy that way anymore. In fact what we find more than anything else is customer’s buy on their own. They’re out there doing their own research there and learning. Frankly, they want to push sales reps, as far back to the end of the purchase as they can. Largely, when they contact them, it’s in the form of some sort of RFP or request for price and there’s very little left to discuss there but terms and conditions.

What we find is that these challenger reps were actually battling against that particular dynamic. Now, the thing that we have to be careful on, about the challenger rep, is you know, as my co-author Matt Dickson, he’s somewhat tongue and cheek, but he’s right. He once said, “You look, we didn’t call them the jerk. We call them the challenger.” What challengers are not doing is being obnoxious. They’re not being annoying. In fact, what you find is the best challenger reps are incredibly professional. They’re incredibly empathetic. They challenge in a culturally correct way. The way you challenge in Japan would be very different than the way you challenge in the Bronx.

But nonetheless, what challenger reps are doing is they’re not challenging the customer as a person, but rather they’re challenging their thinking. They’re expanding the way that that customer thinks about the customer’s own business. Giving them new perspective, a new way for them to think about how to compete more effectively, how to make money or save money that that customer, despite all of their learning, has failed to fully to appreciate on their own. What the challenger Rep is bringing to the table for the customers. Not just a relationship or familiarity. With they’re bringing to the table is what we call insight. It’s an idea about … Not about, the rep’s business and the rep’s products and the rep’s services, but rather about that customer’s business and the customer’s ability to compete.

If you think about … The customer’s that everyone listening to today is thinking about all the customers that all of us serve. The one thing that our customers all want to know more than anything else is, “How can I compete more effectively? How can I grow? How? What are the things I don’t know but should? What are ways I’m exposed to risk that I don’t fully appreciate? What are ways I’m exposed to cost that I haven’t fully understood?” What challenger Reps are doing is they’re bringing that kind of insight to the table. What you find is a challenger conversation is really powerful when done well because the challenger conversation is not the traditional … It’s not products and features and benefits and what we sell and how we can help, but rather, a challenger conversation is really based around a surprising finding about the customer’s own business that shows them a new way to compete that they haven’t appreciated on their own.

Peter: I don’t want to be an over achiever here but when I look at these five types of sales reps. It … And I’m curious about whether your research show these in any way. I would imagine that you need all of this. Meaning that a challenger without having built the relationship wouldn’t have legs. A challenger without also the ability that sort of creatively problem solve to make sure that all the needs are met wouldn’t really have legs. A challenger who’s not a hard worker, et cetera. It would seem that … What I’m curious about from a research perspective is, I would imagine that all of those things without the challenger wouldn’t be very effective in terms of the sales person but the challenger, without all of those things, I imagine wouldn’t either be very successful. I’m curious if you looked at that in the research.

Brent: We did. It’s interesting because this where one can easily fall into the trap of the five profiles and think of them as sort of these very discrete units. Partly, by the way, to be totally fair to everyone out there, that’s sort of how we construct the narrative too, because it makes the narrative stickier, it makes it more memorable, makes easy to wrap your brain around. But you know, I … Now that we’ve worked with literally hundreds of organizations around the world, to help build a … To take them on the challenger journey help train their rep sell, you work with their couches or their managers to coach challenger.

One of the things I often warn them of is that, the question I hear almost inevitably it seems from sales organizations when looking at those five profiles. As you got a room of a 150 sales rep, 400, 500 sales reps. Now look at those five profiles and they’ll ask themselves … In fact, they’ll look at a colleague and say, “Which one are you?” Right. The thing that they’re always … They’re defining the research in terms of the profiles themselves which is largely how we initially tell the story, right? Are you a hard worker? Are you a challenger?

Remember the profiles aren’t meant to be mutually exclusive. I think the better question is not so much are you a challenger? Are you a hard worker? Are you a lone wolf? The better question, I think to ask is, irrespective of whatever profile you think you might be, what in the world are these challenger reps doing that is so different and how can I do some of that too? What I mean by that is at the end of the day, the story isn’t about the profiles, it’s about the behaviors. It’s this specific behaviors that these individual sales reps are engaging as challengers, that allow them to truly be [differentably 00:16:08] better than everyone else.

What you find is there’s certain behaviors in each of those [inaudible 00:16:14] five profiles that create a path to high performance, so you know it’s … We find star performers in each of the five profiles. That, in some ways, not a surprise. What the challenger’s story is more than anything else though, Peter, is a story of probabilities. That is, when you look at the five profiles and look at who’s likely to be a star performer and you had to place a bet, placing a bet on those behaviors that define challenger are by far the best bet to place. Both in terms of what of the data is telling us, but also in just terms of the narrative that we see coming out of that commercial landscape today in given how customers are buying?

So yeah, can you be a star performing lone wolf? Absolutely. In fact, what’s interesting is, there are more star performing lone wolves per lone wolves than there are more star performing any other profile, in that profile. There is, most lone wolves are star performers. When you look at the data, what that might tell you is, “I should just hire a bunch of lone wolves?” What you find in a big sales organization, though is that’s a non-starter, you know. We’ve actually found sales organizations over 75, 80% of their star performers are lone wolves.

What happens is, you live by the sword, you die by the sword at the individual level. It’s really interesting, you have no scale, there’s no process, everyone’s doing their own thing. You can’t really coach to it. One of our heads of sales in a pharmaceutical company very memorably told me one time, he said, “Lone wolves are a cancer in our organization, because everything we’re trying to do is team-based, and they’re all individuals, we can’t sell anything in a team-based organization that way.” What you find is that while you can be a star performer in any one of these five profiles engaging in the behaviors that define challenger [irrespect 00:17:49] of whatever profile you may be in, is what we find to be the best way to maximize likely at being a star performer.

Peter: In a few minutes that we have remaining, Can you share some of those behaviors of the challenger?

Brent: Sure. There’s three in particular, we dive into this in more detail in the book but the finger print of a challenger rep really is, is the ability that, what we call teach, tailor and take control. To teach the customer something new about the customer’s business. Not about our products and services, it’s about what the customer is actually doing or not doing. That would allow them to be more competitive on ways the customer hasn’t fully appreciated. By the way, that’s going to involve two-way communication. It’s going to be, it’s going to involve not leading with questions but rather leading with insight. But nonetheless being able to ask good follow-up questions once you’ve led with that insight to engage customers around that insight. To have that conversation. To tailor is to-

Peter: [crosstalk 00:18:38] One of the things you speak about. That one of the things you speak about in the book, and this actually might be tailored but it might be teaching. I can’t remember what section you had it in but the idea that you want to teach about issues that position you as the person trying to sell them. Your product in a way that makes it an obvious solution to the challenge that you’re teaching them about.

Brent: Yeah, that’s an important part of the story which is, if I go out, said and say, like you know, we get this question a lot. It’s the right question to ask which is, “All right Brent. Let’s say, I do what you recommend we do. We want to teach the customer something new about their business, show them a new way to compete.” They get all excited, say, “You’re right, I got to do that.” Then they take that idea, put it in our RFP, put it out to bid and your competitor wins the business, that doesn’t feel like a good place to be.

We have a name for that, we call that free consulting, and very few people ever made much money off of free consulting. I think, [deferentially 00:19:29] no one did. What one has to do when one teaches the customer about the customer’s business is make sure that whatever you teach the customer about their business ultimately leads back to something that you can do better than anyone else. That your insight leads to your unique strength but the whole idea here is a couple thoughts on that, is one that means you actually have to know what your unique strengths are, which turns out to be a really hard part of the story which is not just ask, what are we good at? But what are we uniquely good at?

But then once you identify what those unique strengths are, rather than doing what most of us are trained in and instinctively would want to do is to go out and tell the world what we’re uniquely good at and lead with that as our valued proposition. What we talk about in the challenger’s story of teaching is don’t leave with that value proposition but lead to it. Because your customer doesn’t want to have a conversation about your company, they want to have a conversation about their company. How they could be more competitive in ways they haven’t fully appreciated.

Have that conversation first. Share that insight. Blow them away or challenge them with new perspectives that allow them to achieve goals they didn’t know were even achievable but do it in such a way that at the end of the conversation when they ask the inevitable question, “Great. That’s fantastic. But who can help you with this?” You gotta be able to look them in the eye and say, “All right, well, let me show you how we’re positioned to help you with this better than anyone else.” The way we summed it is we like to say, “Don’t lead with, lead to.” In many ways, that’s the heart and soul of teaching in challenger.

Peter: Great. Tailor?

Brent: Tailor is all about understanding who your customers stakeholders are and what they care about? What are their priorities? Also to understand that customers’ business. It stands the reason, if I’m going to teach the customer the way to make money or save money, I need to actually understand how they make money or how they save money. I need to understand their business, inventory turns, their through put, or risk Gallup foot print or whatever it might be that’s going to allow you to tailor your insight to what their current position is and how they perform against that insight.

To finally, to take control. I think, in some ways, Peter, this what the one that gets us in most trouble because it sounds so annoying and aggressive. But take control means to essentially, well to take control of the conversation, diplomatically, professionally, empathetically, culturally correctly. But nonetheless to steer the organization. Rather being on your back foot of asking, “What do you need? What’s keeping you up at night? How can I deliver value?” You start that conversation on your forward foot saying, “I got something to share with you, I think would be important for your business to see.” That you keep that conversation based and revolving around that insight, around value as supposed to following back on price and a pure negotiation.

To do that in a way that allows you to, as we like to say, to pressure the customer, but not pressure them personally but to pressure their thinking, to take the customer a little bit out of their comfort zone to get them thinking about their business in ways that they haven’t really thought about it in the past. Teach, tailor, take control. Again, whatever profile you might think yourself to be in. That we find is a recipe for improving performance for anyone.

Peter: Brent, Thank you so much. Like the book itself, the podcast that you’ve just recorded with me is really filled with a lot of really great information that takes some time to absorb because it’s not just about knowing something more, but it’s about showing up differently and doing something differently as a sales person. I really enjoyed both the Challenger’s Sale and the Challenger Customer. It really made me re-think, I mean, the way that we sell, when were selling in organizations is very consultative. But it gave me, some shape to think about how I do that very specifically. I really appreciated reading the book. I think it’s a great book. Thank you so much for being on the Bregman Leadership Podcast.

Brent: Absolutely, Peter. Thanks for having me.

Peter: If you enjoy this episode of the Bregman Leadership Podcast, please subscribe and leave a review on iTunes. For more information about the Bregman Leadership Intensive, as well as access to my articles, videos and podcasts, visit Thank you to Clare Marshall for producing this episode and to Bryan Wood, who created our music. Thanks for listening and stay tuned for the next great conversation.


  1. Linda says:

    Excellent podcast! Such a fresh perspective!

  2. Basil says:

    Hi Peter

    Thanks for sharing this.
    Really insightful and thought-provoking travel-aid to one’s journey of holistic self-improvement (not just as a sales-person).

  3. Natalia Hernández says:

    Thanks for doing this podcast. Invaluable information from CEB!!! great interview!

  4. LSE says:

    This is really very good. I’m not a sales person but it makes a TON of sense for communicating and “selling” within your own organization.

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