Buyers know more than you do. At least, that’s what they want you to think.

You can thank Big Data for that. Today’s buyers know more about you, your competition, and the sales process than ever before. As a sales leader, you’d better provide some unique value, or else you can count on that buyer moving on.

So how do you do it? “The Challenger Sale,” a popular sales model created by Matthew Dixon and Brent Adamson of the Corporate Executive Board, says that it’s really all about insights and the customer experience.

We compiled a list of our 5 favorite blogs on The Challenger Sale to break down what it’s all about and what it means for your sales organization.

A 5-Minute Summary of “The Challenger Sale” Book Your Boss Told You to Read by Justin Mares

A major feature of The Challenger Sale is its 5-pronged salesperson classification. According to The Challenger methodology, every sales rep can be categorized into 5 profiles: The Hardworker, The Lone Wolf, The Relationship Builder, The Problem Solver, and The Challenger.

This quick summary post of The Challenger Sale by Justin Mares highlights the qualities of each profile, noting that 40% of top-performing sales representatives used a Challenger style. However, Mares says today’s sales organizations are geared toward developing sales reps who are Relationship Builders, which is the least effective of the 5 styles. The Relationship Builder is the classic consultative sales rep, someone who relies on developing relationships with buyers to close the deal.

What qualities and skills do Challenger-style reps display?

  • Different view of the world
  • Love to debate/push customer out of comfort zone
  • Strong understanding of customer’s business


The Challenger Sale: Not Very Challenging by Geoffrey James

To differentiate themselves from the noise of competition, salespeople must be able to provide buyers with unique insights from the first conversation. That’s a main premise of The Challenger Sale.

However, according to Geoffrey James, this is old news. He says the concept of insight selling has been around for decades, but is now being repurposed for the Big Data generation.

In The Challenger methodology, insights often come in the form of provocative questions and debates. As a salesperson, you’re encouraged to challenge the buyer, to take control of the sale, and to prove to the buyer that you know more about their business needs than they do. This process can alienate the customer if they perceive a controlling conversation as a hard sell, though.

James says controlling the sale is “seductive and illusory,” because it masks the uncertainty of sales and doesn’t work.


Challenger Selling: “Courageous Questions” Differ from “Grenades” by Michael Dalis

The Challenger Sale model has become popular among sales leaders looking to develop salespeople who can have effective meetings with prospects. An aspect of The Challenger Sale is the ability and willingness to ask “challenging” questions to prospects.

The purpose of posing challenging questions is to provide insight and value to the conversation, but according to Michael Dalis, the delivery of these questions can either be perceived as “courageous” or “grenades”.

What’s the difference? A courageous question is one that is relevant to the client. It’s direct, delicate, challenges current thinking, insightful, and thought-provoking. A poorly received question is a grenade, and it will behave like one. You could be blowing up an opportunity.

The ability to craft and deliver an effective courageous question is both an art and a science. Dalis says many factors play into the success of a courageous question, and offers 8 best practices for integrating them into a sales dialogue:

1) Know where you stand

2) Establish trust

3) Establish credibility

4) Prepare and practice

5) Choose an appropriate setting

6) Set the context

7) Structure the question carefully

8) Allow silence, and listen.


Challenger Sales Model In Just 8 Minutes by Lindsay Kolowich

Successful B2B companies realize the need distinguish themselves from competition. The challenge lies in identifying the best method for differentiation. What variable do you change?

Cost? Brand impact? Product delivery? None of the above, says Lindsay Kolowich in her post for InsightSquared. The key to brand loyalty, according to The Challenger Sale, is customer experience.

According to The Corporate Executive Board, 53% of customer loyalty is attributed to the buyer’s experience. For a quota-carrying sales rep, closing the sale may be the be-all, end-all. But the busy executive has already done their due diligence before you even meet, so the buying process must be valuable. Kolowich says offering strategic insights, consultations, free content, etc., ensures your prospects that you are the right choice for the deal.


The Challenge with The Challenger Sale by Drew Zarges

The Challenger Sale is appealing. In a perfect situation, it would help sales organizations develop reps who are provocative, provide insight and value to buyers, and close more deals.

But it’s not for everyone.

Drew Zarges says The Challenger Sale, like any sales methodology, is an investment. It’s an investment in time, money, and people. It demands change management. There are 5 main factors to consider in deciding to adopt The Challenger Sale: organizational structure, talent, coaching, marketing alignment, and efficiency.

The techniques of The Challenger Sale aren’t unattainable. But Zarges says sales leaders must be prepared for the full commitment to making the methodology an ingrained part of the organization’s culture before trying to take on this strategy.

Our Point of View

We believe The Challenger Sale is a great concept. If you review the ideas above, it’s evident that there are some seriously beneficial outcomes to implementing Challenger strategies. However, like with any cutting-edge idea, there are — excuse the pun — challenges.

Adopting The Challenger Sale model and scaling it for a sales organization is easier said than done. It puts a lot of pressure and a high demand on the salespeople. Developing a team of salespeople who are disruptive and confident, but not aggressive or confrontational, requires balance.

Are you up for the challenge?