The Challenger Sale — How to Navigate Complex Sales Conversations

The Challenger Sale, by Matthew Dixon and Brent Adamson, lays out a clear path to successfully navigating complex sales in an ever-changing economy. This book is one of the top three books we recommend to our clients.

Read it here: AmazonAudibleBookshop

Whether you’re looking for a quick overview to get started, or have already read it and need a refresher, this summary of The Challenger Sale is designed to give you the key highlights of this proven sales methodology.

The Five Types of Sales Reps, According to The Challenger Sale

In the Challenger sales model, all sales reps fall into five categories. These categories are not static – a rep can belong to one category while sharing characteristics with other categories. Also, because many of these are skill-based, by growing their skill set, a rep’s type can change over time.

The five types of sales reps listed in The Challenger Sale are:

  1. Hard Worker – The sales reps who believe that simply by putting in more hours than anyone else they will pull in more deals or revenue.
  2. Lone Wolf – These are the reps that pull in huge numbers, often out of instinct rather than any methodology. They don’t like to be managed, and typically don’t play well with others, but are tolerated because they constantly outperform their peers.
  3. Reactive Problem Solver – These reps are excellent problem solvers, but they tend to focus more on providing excellent customer service than generating new sales.
  4. Relationship Builder – These sales reps are focused on building strong networks of relationships with their clients, but because they tend to avoid conflict or debate, they don’t sell as much as they could.
  5. Challenger– Challenger reps are assertive debaters who develop a deep understanding of customer needs.

Each of these types can be low achievers, but many sales managers would be surprised to learn that Challenger Reps typically lead the pack in terms of performance while Relationship Builders tend to be some of the lowest performing reps overall. That’s one of the main reasons we recommend the Challenger methodology to clients dealing with complex sales.

So how do you find (or become!) a Challenger Rep? The good news is — anyone can be taught to be a Challenger — these types of reps are made, not born. The Challenger sales model is based on demonstrated behaviors. It’s not about who you are but what you do.

Essential Skills for Becoming a Challenger Rep

There are three key things that Challenger Reps do well:

  • They teach prospects something new and valuable about how to compete in their market.
  • They tailor their sales pitch to resonate with each stakeholder’s hot-button issues.
  • They take control of the sales process by creating constructive tension and a sense of urgency.


While most sales reps start the conversation talking about their own product and company, Challenger Reps focus on teaching the prospect something new and valuable about a problem or opportunity their business is facing.

After fully understanding the prospect’s situation, a Challenger Rep provides an expert perspective gained from their broader view of the industry.

6 Steps of a Teaching Conversation

There are six steps to a teaching conversation in the Challenger sales method:

  1. Warmer – After the initial introductions, a Challenger Rep lays out the challenges they’re seeing and hearing from other companies in the prospect’s industry, setting themselves up as the expert who is already knowledgeable about the prospect’s business.
  2. Reframe – This is the core of the conversation. Challenger Reps offer insights into the prospect’s company to make them aware of a new problem or opportunity at hand.
  3. Rational Drowning – In this step, a Challenger Rep provides data to support the identified problem or opportunity. This step is meant to be uncomfortable for the prospect, as they realize the full scope of what they’re facing.
  4. Emotional Impact – To really bring the issue home, Challenger Reps tell a story that is so relatable that the prospect can see themselves in it. This is the gut punch. At this point, the prospect should feel almost physically ill as they worry about the problem that was brought to life by storytelling.
  5. New Way – After driving the issue home, the Challenger Rep starts to alleviate the prospect’s concern by delivering a solution. This is still not about the rep’s company; it’s strictly about the range of solutions available to the prospect.
  6. Your Solution – Now and only now do Challenger Reps mention their company and their specific solution. This is where they say “Here is how we can fix the problem.”

Challenger Reps reveal the problem, then provide insight and a solution that eventually leads back to the unique strengths that the rep’s product or company has to offer.

To increase urgency, the Challenger Rep then drives home the cost of INaction. At no point in the conversation is a rep justifying the cost of their product. Instead, the focus is on what will happen if the prospect does not do anything.

Every part of the conversation is focused on driving the prospect to take action.

To recap teaching:

  • Identify the problem the prospect doesn’t know about.
  • Identify the solution that leads to your company’s unique strengths.
  • Explain the cost of INaction.


Being a Challenger Rep is about more than just teaching. To truly resonate with their prospect, Challenger Reps tailor their message to the individual in front of them. Their sales pitch is tailored to each person they speak with, and that person’s unique priorities as it relates to their position in the prospect’s company.

In complex sales, it’s unusual to get a direct line to the top decision maker. Challenger Reps overcome this by tailoring their message to each individual stakeholder in the decision-making chain.

While the main content doesn’t change, the rep will highlight different features or tell different stories to connect individually with each stakeholder. While this might seem like too much work, it pays off in the long term as it makes each team member feel heard and valued.

Since team buy-in is often a key factor for top level decision makers, taking the time to make sure their entire team is on board makes them much more likely to pull the trigger when it’s time to purchase.

To recap tailoring:

  • Complex sales often require selling to multiple people in the decision-making chain.
  • Focus on the goals and needs of the individual in front of you, and use these to tailor your pitch and storytelling.
  • Remember that team buy-in is an important factor for top-level decision makers.

Taking Control

Teaching and tailoring are valuable, but taking control is the step that makes Challenger Reps rise above the rest.

While many sales reps avoid taking control – either from their own lack of self-confidence or a desire to please the prospect, Challenger Reps sell with confidence because they know they’re adding value to the conversation. Taking control isn’t about being aggressive. It’s about being assertive and knowing how to stand your ground when a prospect pushes back.

Challenger Reps are comfortable pushing to the next stage of the deal. By taking the lead in the conversation, they’re equipped to challenge their prospect’s thinking, helping prospects focus on the areas of value offered without landing in the weeds of indecision or over-emphasis on the bottom line. Challenger Sales Reps are comfortable talking about money, and aren’t afraid to push.

To recap taking control:

  • Be confident in the value you provide to the prospect.
  • Own the conversation – don’t be afraid to take the lead and ask hard questions.
  • Help the prospect move toward action by creating a sense of urgency.

4 Key Principles of Challenger Sales

1. Challengers Are Made, Not Just Born

While some reps may lean naturally toward this style of selling, many will not. The good news is that the Challenger sales method can be taught, and reps can learn how to leverage constructive tension to move prospects into action.

2. It’s the Combination of Skills That Matters

Of the three challenger attributes — teaching, tailoring, and taking control — the power lies in the combination more than any particular part. If you teach without tailoring, you become irrelevant. If you tailor but don’t teach, you won’t really stand out from the competition. And if you take control without offering value, you’ll come off as bossy and unhelpful.

3. Challenging Is About Organizational Capability, Not Just Skills

In order to ensure a consistent message, the content of the teaching pitch needs to come from the organizational level, not just individual reps. By using a high-level view to categorize customer needs and insights, companies can equip their reps with resources tailored to each specific customer type, empowering reps to effectively take control of the sales interaction.

4. Building a Challenger Sales Force Won’t Happen Overnight

The Challenger sales method is an entirely different way of approaching sales, and the changes required won’t happen overnight. Moving to a Challenger model is a commercial transformation that takes time to get it right.


In this summary of The Challenger Sale, we’ve covered how to teach, tailor, and take control in complex sales conversations. You’ve learned the six steps of a teaching conversation, and how to tailor your pitch to encourage buy-in from the entire decision-making team. Of course, if you haven’t already, we highly recommend reading the book – find it on AmazonAudible, and Bookshop.

Interested in a blueprint on designing your own sales team? Purchase our Sales Team Starter today!