In our first two blogs, we explored why traditional relationship selling no longer wins consistently in complex B2B environments, and we broke down the five types of sales reps identified in The Challenger Sale by Matthew Dixon and Brent Adamson.
Now it is time to dig into what really makes the Challenger stand apart: the three behaviors that consistently define top performers: Teaching, Tailoring, and Taking Control.
This trio is not just a catchy framework. It is what transforms an ordinary seller into a trusted business advisor.
Every buyer wants value, but few can clearly articulate what that means. That is where the Challenger comes in, not by pitching, but by teaching something new about the customer’s own world.
Instead of asking, “What keeps you up at night?” Challengers tell the customer what should keep them up at night.
They teach through insight, helping buyers see hidden costs, missed opportunities, or unrecognized problems that their solution can address.
In the book, Dixon and Adamson emphasize that this kind of teaching reframes how buyers think about their business. The best Challengers do not sell by explaining features. They sell by making the customer say, “I have never thought about it that way before.”
Teaching gets attention. Tailoring earns trust.
Once the Challenger introduces a fresh perspective, they make it relevant. That means adapting the story to resonate with each stakeholder, from the CFO who cares about risk and return, to the end user who needs efficiency.
According to the research behind The Challenger Sale, this ability to personalize the message is one of the biggest predictors of success in complex deals. Buyers respond when they feel understood, and Challengers do their homework to make sure every conversation feels custom-built.
Tailoring also extends beyond what you say. It is how you listen. The best Challengers use discovery to learn the customer’s language, then reflect it back with precision. It is empathy paired with authority.
This is where the Challenger earns their name.
Taking control does not mean being pushy. It means confidently guiding the conversation toward value, especially when the buying process gets messy or stalls out.
Challengers are comfortable with healthy tension. When a buyer hesitates, they do not immediately offer discounts or back down. Instead, they reframe the risk of inaction, reminding the customer why change matters.
The book’s data is clear: top performers push their customers’ thinking, but they also push deals forward. They know when to slow down for alignment and when to take the lead.
That is what makes their sales process feel more like a partnership than a pitch.
When you combine Teaching, Tailoring, and Taking Control, you get a rep who does not just close deals, they change how customers buy.
They are trusted not because they are the friendliest or most persistent, but because they bring clarity and conviction to every interaction.
The Challenger’s secret is not just confidence; it is preparation. They study their customers deeply enough to challenge them intelligently. And when they do, buyers follow their lead.
The best salespeople do not simply react to customer needs, they shape them.
Challengers win not by being aggressive, but by being insightful, adaptive, and confidently in control. They create value in the conversation itself, long before a contract is signed.
That is the Challenger difference.
And that is what WingRep is here for, to turn every salesperson into the best version of themselves through accessible coaching.
Next in our Challenger Sale Series: How to Build a Challenger Sales Team: Turning Individual Strengths into a Scalable Strategy.
.png)
