June 23, 2026

The Challenger Sale by Matthew Dixon and Brent Adamson

the-challenger-sale-cover
Reading Time: 3 minutes

Now that I’m using Reading Refresh to keep myself up to date on books I’ve read in the past, I thought I’d share some of them as they came back up. Today is Matthew Dixon and Brent Adamson’s “The Challenger Sale“. This book is also available as a free flashcard deck on Ripple Recall.

It’s been a couple of years since I read “The Challenger Sale”, but many of the ideas have stuck with me over that time. It’s an interesting approach to sales, and one that is worth revisiting from time to time.

The book talks about the five types of salespeople, and almost everyone can see which bucket they fall into as they read the book. The five are:

  • The Hard Worker
  • The Challenger
  • The Relationship Builder
  • The Lone Wolf
  • The Reactive Problem Solver

Of course, as the title would suggest, they see one of those as being the best and spend most of the book explaining how to become a challenger.

The book teaches the “six steps of a world-class teaching pitch”, which go like this:

Step 1: The Warmer

“We’ve worked with a number of companies similar to yours, and we’ve found that these three challenges come up again and again as by far the most troubling. Is that what you’re seeing too, or would you add something else to the list?”

It’s an approach we’ve dubbed “Hypothesis-Based Selling.” Rather than leading with open-ended questions about customers’ needs, you lead with hypotheses of customers’ needs, informed by your own experience and research.

Step 2: The Reframe

Remember, the reaction you’re looking for here is definitively not, “Yes! I totally agree! That’s exactly what we’re working on!” but rather, “Huh, I never thought of it that way before.” If your customer’s first reaction to your insight is enthusiastic agreement, then you haven’t actually taught them anything.

Step 3: Rational Drowning

Rational Drowning is where you lay out the business case for why the Reframe in step 2 is worth your customer’s time and attention. So now it’s time for the data, graphs, tables, and charts you need to quantify for the customer the true, often hidden, cost of the problem or size of the opportunity they’d completely overlooked.

Step 4: Emotional Impact

Emotional Impact is all about making absolutely sure that the customer sees themselves in the story you’re telling. There’s nothing more frustrating than laying out a compelling argument and hearing your customer say, “Yeah, I see what you’re saying, and I’m sure it makes a lot of sense for a lot of your customers. But I’m struggling to see how this applies to us. We’re different.”

Step 5: A New Way

As tempting as it might be at this point to launch into a review of how you can help, step 5 is still about the solution, not about the supplier.

Don’t rush this. Before they buy your solution, the customer has to buy the solution. You’re looking for your customer to say something like, “You’re right, that makes total sense. That’s what we need to do,” or “That’s the kind of company I want us to be.” Now they’re ready for step 6, Your Solution.

Step 6: Your Solution

Now you can unveil your amazing solution.

Of course, the value of a process like this depends on what you’re selling, and it lends itself better the higher the cost is for your product.

I find myself naturally drawn to the “relationship builder” style, so I found this approach to be quite different (but helpful). One of the best things I took away from the book was the concept of the “Deb Oler Question”, which is shockingly simple:

“Why should our customers buy from us over anyone else?”

I challenge our clients with this quite often, and they sometimes have a hard time with it. If they can’t answer that themselves, how on earth could they expect customers to do it?

I encourage you to give it a read. You can pick up the book on Amazon, hit the free study deck at Ripple Recall, or watch this short overview video for a bit more:

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