The Challenger Sale: Teaching, Tailoring, and Taking Control (Book Digest)

"The Challenger Sale" advocates for an assertive approach to sales based on teaching customers something valuable that leads them to want what your product offers, tailoring messages to different stakeholders, and taking control of the sales process. This approach stands in contrast to traditional sales approaches that are focused on building personal relationships or asking questions to uncover needs.

The Challenger Sale's key insight is that success is as much about proving that the customer needs to act and shaping their decision criteria to set your product up to win as it is about pitching your product.

The End of Relationship Selling

The Challenger Sale argues that sales reps often focus too much on building relationships. Some efforts to build relationships, in their view, harm sales efforts more than they help.

The authors support this point by identifying five distinct seller profiles and measuring their performance:

• Hard Workers: High activity level, persistent

• Relationship Builders: Focused on customer happiness and accommodation

• Lone Wolves: Instinctual sellers who follow their own rules

• Reactive Problem Solvers: Responsive and service-oriented

• Challengers: Those who press customers on their thinking

Challengers consistently outperform all other rep types, particularly in complex solution sales. Relationship builders often get taken advantage of when they take actions to increase customer convenience without securing sales progress in return.

Interestingly, Challenger reps often end up having good relationships with their customers, but those relationships are a consequence of a successful business partnership, not the cause of it.

Teaching for Differentiation

So how do Challenger's succeed? The first pillar of the Challenger approach is to teach customers something valuable that leads them to want what your product offers.

This is different from traditional question-based selling methods that seek to uncover the customer's needs. These question-based methods assume that customers know what they want.

The Challenger Sale argues that customers often don't know what they need.

Challenger reps fill this gap by telling customers what they need using an approach called commercial teaching. Commercial teaching isn't directly about your product; it's focused on helping customers understand their challenges and the markets in which they operate.

Customers come to understand their needs in a way that naturally leads them to look for a solution like the one you offer. You lead to your solution, rather than leading with it.

Good commercial teaching:

1. Leads to your product's unique strengths

2. Challenges customer assumptions

3. Catalyzes action by showing the costs of inaction

4. Scales across customers

The teaching conversation follows a structured path:

1. The Warmer: Begin by establishing common ground about industry challenges

2. The Reframe: Connect these challenges to either a deeper problem or larger opportunity

3. Rational Drowning: Present data and evidence showing why the challenge matters

4. Emotional Impact: Tell stories that make customers see themselves in problematic situations

5. A New Way: Outline the capabilities needed to solve the problem

6. Your Solution: Demonstrate why your offering is best suited to deliver those capabilities

W.W. Grainger implemented a great example of this approach. Granger makes maintenance equipment. They realized that their customers considered them a transactional supplier of commodity products without much differentiation from competitors.

As Granger sought a better way to sell their services, they realized that their customers were purchasing maintenance equipment inefficiently by making unplanned purchases. Grainger’s unique capability was being so reliable and comprehensive that customers didn’t need to make unplanned purchases.

Granger's pitch started by showing that unplanned purchases come at a steep price because they take extra time and are made at full retail price. Then they showed that Grainger has the ability to prevent these last minute purchases across many areas of spend.

Notice that Granger discusses their capabilities only after they share an insight that primes the customer to want the capabilities they offer.

Tailoring for Resonance

The second pillar of the Challenger approach involves customizing messages for different stakeholders. In today's complex sales environment, decisions are often made by consensus rather than by a single high-ranking economic buyer. That means that it's important to nurture a broad group of supporters.

Nurturing support among a broad group of stakeholders requires keeping them engaged and tailoring your message to what each stakeholder most cares about. These are some key elements of the approach:

• Adding informational value with each interaction

• Understanding how industry trends affect specific companies and roles

• Focusing on each stakeholder's desired outcomes

Companies should give reps the resources to tailor effectively. Solae, a manufacturer of soy-based food ingredients, created "outcome cards" for each stakeholder type listing what that stakeholder wanted out of the purchase. They also developed pitch guidance connecting their products to the specific outcomes each role valued.

This enabled their sales team to tailor the company's message to what each type of stakeholder needed.

Taking Control of the Sale

The third pillar of the the Challenger approach is taking control. This means confidently directing the sales process and being willing to discuss difficult topics like money.

Challenger reps trade sales effort for sales progress, like access to decision-makers. They aren't afraid to walk away from opportunities that demand effort without advancing the deal. They know that many "opportunities" are just due diligence by buyers who aren't really interested.

Taking control includes:

• Requiring access to key executives in exchange for sales efforts

• Setting expectations about investment from both sides

• Telling customers how to buy, not assuming they know

• Pushing back respectfully, particularly on pricing issues

• Being comfortable with silence and leaving negotiation points open

This approach works because selling companies have done many implementations while buying companies have done very few. Reps need to recognize the value of their expertise and leverage it appropriately.

Conclusion

The Challenger Sale presents a fundamentally different vision of effective selling. Rather than being agreeable and relationship-focused, the most successful salespeople are memorable.

They teach customers about problems they didn't know they had, tailor their messages to each stakeholder, and confidently take control of the sales process. The key is not to tell customers about your differences, but to make them value those differences through effective teaching, tailoring, and taking control.

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If you liked this article, have a look at our other book digests in our series Required Reading for Salespeople. You can also check out the P.S.I. Selling Content Page for more insights on sales communication, strategy, and leadership.

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For more about the author, check out Mike's bio.