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Way back when—amid another weird economic downturn—a couple of smart people did some research around sales teams and characteristics of top sales performers. That research led to the Challenger profile and The Challenger Sale book.

I've since worked with multiple sales teams who adopted the Challenger Sale approach, many with great success.

(If you're curious check out this summary post from Pipedrive. If you're super curious, check out the book [and its companions].)

I'm not here to give you a summary. But I am here to talk about continued challenges of applying the Challenger approach well.

Easy-to-Remember Approaches Often Turn Into Formulas

The Challenger Sale has been around long enough that some people treat it like a formula. And, let's be real, it was designed to sound formulaic:

  • Three overarching themes: Teach, Tailor, and Take Control.
  • Five steps: The Warmer, The Reframe, Rational Drowning, Emotional Impact, A New Way, Your Solution

It's a neat, beautifully wrapped package. Easy to remember themes and steps. Works well for training and reinforcement with sales teams.

But we're doing real talk today: Sales teams let it slide into a formulaic approach; creating custom pitches is a lot of work!

  • PowerPoint and Google Slides are not delightful programs to work in if you don't have keyboard shortcuts memorized.
  • Sales teams are given a deck library to plug-and-play, but also highly customize with powerful insights and stories.

You and I both know the reality is usually this: "What was the last presentation that did really well? Let's copy that and update each step."

Formulaic. It happens, but it misses the point of The Challenger Sale.

Instead, we need to think of it as jazz.


There are some principles, sure. But the point is improvisation, creativity, and responsiveness to your audience.

That's how you really teach, tailor, and take control of your audience without being formulaic.

There's an art to it.

Jazz Lessons From a National Treasure

Lindsay Gibb started watching every Nicolas Cage movie she could on a bit of a lark. She ended up doing extensive research and writing the book">National Treasure: Nicolas Cage.

I started a Nicolas Cage: Good or Bad article series on a bit of a lark, and now we're talking about how to think differently about the challenges of the Challenger Sale.



Seriously, though, let's talk about why Lindsay Gibb says Cage's "acting is akin to jazz." And what in the world that has to do with overcoming the formulaic.

To do a Challenger Sale well, you first have to grab attention (The Warmer). If you've been following this series—or you've watched any Nicolas Cage movie—you know there are moments when you wonder, "What just happened?!" And if nothing else, the moment does grab your attention.



Salespeople are naturally pretty great at coming up with a good opener. A hook to get things started. It's often the middle where things get messy. So let's start there.

Nicolas Cage's approach to acting ends up being all about a growth mindset.

"He wants to feel uncomfortable, so he can learn from the experience. His desire to learn is the main influence on his choice of films. He looks for something that will challenge him by making him try something he hasn't tried before," writes Gibb in National Treasure.

The Challenger profile for salespeople is all about being curious learners who want to stay on top of trends and constantly seek out new insights. Because they know that's what fuels their ability to challenge clients.

That's why one of the themes is Teach. Sharing a challenge to status quo thinking in The Reframe sets the salesperson up to challenge their clients to follow A New Way path. And that doesn't typically happen on its own. It requires an assist.

"Cage consistently encourages viewers to question our assumptions and expectations about actors and acting, about art in general. And above all, he's always trying. And that's what makes him great. He's earnest even when it would be much cooler not to care." (Gibb again.)

The journey from The Reframe to A New Way requires two seemingly incompatible steps: Rational Drowning and Emotional Impact.

Messing with the client by overloading rational thought to make them feel bad, and then tugging on their heart strings? The Challenger Sale can come off sounding like only jerks need apply.

And that could end up being what clients think if you take a formulaic approach.



The Challenger Sale is not about being a jerk. It's about being an iconoclast who cares enough to encourage clients to "question assumptions."

Think of Rational Drowning and Emotional Impact as ways to raise the stakes and set up A New Way as a pressure release valve.

Cage does that by experimenting with larger-than-life physicality, reactions, and character interpretations. These moments seem as if they came out of left field, and they feel intense. But Gibb argues that those seemingly random over-the-top moments came from a place of "hyper-preparedness."

If Cage's performances were only over the top, I doubt he would have gained much notice. Gibbs emphasizes Cage's "never wanting to get into a rut"; instead, he "heads into new territory."

That combination of hyperpreparedness and always wanting to chart new territory also drives successful Challenger salespeople.

When salespeople have both the drive to take action and the discipline to properly prepare, the results are dynamite. When they go further and "push the boundaries of what is comfortable, what is expected," that's when you get the magic. That is the unexpected journey that winds its way through the seeming contradictions of Rational Drowning and Emotional Impact.

The key to this step is that bit of jazz: Be responsive to your audience. That takes both preparation and improvisation.

"Cage's genius comes from his willingness to do whatever works for him despite what's expected. His choices are hard to reconcile because each movie he makes is for a different audience." (Gibb, once more.)

When you truly customize your story to your audience, it becomes a lot easier to have a conversation that leads to New Way of thinking.

"Cage doesn't believe in 'over the top.' Instead, he believes in taking risks, trying something new, and working outside of the box." (Gibb.)

The client shares a pain point. A formulaic approach treats the symptom with easy-to-sell solutions.

But the Challenger Sale goal is to get the client to think differently:

  • Dig deeper for the uncomfortable root cause truth with a Reframe.
  • Underline that root cause with magic marker insights in Rational Drowning.
  • Unique way of thinking about the status quo with an Emotional Impact moment.
  • Layup for the New Way (AKA, a tailored, unique solution that solves the root cause).

Formulaic approaches feel safe. But you need to get uncomfortable. Help your clients take some risks by getting them to think beyond boundaries and try something new.

More Resources on Sales Enablement Strategy

Four Ways to Tackle Your Sales Enablement Strategy During and After the Pandemic

How to Use ABM Tactics to Support Sales and Influence Buying Committee Decisions

How to Drive Sales and Marketing Alignment in an Enablement Role

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What Nicolas Cage Can Teach Us About the Challenger Sale

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image of Cathy Colliver

Cathy Colliver is the marketing director at Test Double, a software consulting agency. She loves simplifying challenges, and her marketing career spans five industries. Cathy volunteers in arts and education.

LinkedIn: Cathy Colliver

Twitter: @CathyColliver