The Challenger Sale Book Summary

This summary includes everything that wasn’t obvious to me while reading it and some of the things that were obvious but I thought it’s important to mention and always remember.

The writers manage the Sales Executives Council and the Marketing Leaders Council and base this book on years of research.

Who is the star Salesperson?

There are 5 types of sales people:

  • The Problem Solver
  • The Lone Wolf
  • The Hard Worker
  • The Relationship builder
  • The Challenger

The relationship builder is too nice and too pleasing which makes him the loser in most cases.

The Challenger is the clear winner in most cases, excluding some cases of the Lone Wolf who could be a unicorn in their current industry/role.

The challenger has 3 main characters:

  • They educate the clients
  • They take control
  • They tailor the messages

Be a Challenger

You should always personalize your sales pitches, not only to the specific client but to the person’s role in the organization.

Taking control is not only about assertiveness and being able to negotiate and insist on a price. It comes naturally once the salesperson is in the position of the educator.

When asked what drive solution loyalty, buyers responded:

  • Price – 9%
  • Brand, product, and service – 38%
  • Proving expertise during the sales process – 53%

Proving expertise

When asked what proves expertise:

  • Being able to navigate through the alternatives to the solution
  • Offers an advice
  • Has an expert view on the market and business problems
  • Suggests how to avoid landmines while picking the right service

Educate your clients

Teach your clients and provide them insights about their business. Ideally, insights they haven’t thought about before.

Teach them lessons and provide insights that lead back to your unique and best strengths. Always find relevant insights that lead back to your business.

Get them to act by framing the problem in numbers. Help them to calculate the ROI of fixing the problem, not the ROI of using your product.

Suggest help to get it done and offer a free consultation. Help them navigate through their options.

Try to figure out what each stakeholder cares about now. Insist on key stakeholders to participate in the conversation. If they don’t, the lead is probably not really interested.
Teach them not only how to buy the solution, but also who should participate and why.

Ask yourself the question: “What costing our customers more money than they realize that we’re the only ones who can help them fix it?”.

The sales pitch steps

Optional and not part of the book (saw it in a LinkedIn post by Gong today and thought it’s relevant) – to start with an up-front contract. “Today we’ll see whether our product is a strong fit so that you know your time in this process is well spent. If we agree that it’s useful after our conversation, we’ll loop in your team to continue building a use case. Is that fair?”.


“When we talked to similar companies we kept hearing about the same 3 challenges. Are you experiencing the same challenges or want to add others of your own?”

Choose the challenges that they probably undervalue.


Connect these challenges to a bigger opportunity. Why it matters? Describe real-life “imaginary” situations without mentioning clients yet.


Help them understand the value of fixing the problem in numbers (ideally $). Don’t talk about the ROI of your product.

“You said you are making between $10M-$50M per year. That means that solving this problem could save you between $100K-$500K per year.”

Get personal:

Tell a story about a similar company. Describe the problem they had and the fact they solved it and what was the impact on their business.


Teach about possible solutions.

There’s a growing trend for companies to use Product Line for X, Y & Z. The reason is A, B, C. I expect it to evolve to D.

Our solution:

Lastly, tell them how and why your solution fits them best

Sales managers

Great Sales managers are about 3 things:

  • Coaching
  • Resources management (time, budget, reps, collateral)
  • Innovation in deal strategy – the ability to get stuck deals unstuck by asking prompt questions that question reps biases

A great tool is the SCAMPER technique.

Most reps forget most of the training 30 days after the training is over. Organizations should always keep the information fresh in the reps’ minds.

Marketing takeaways

A successful sales operation relies heavily on marketing to:

  • Collect business insights to share with potential customers
  • Tailor messages to every stakeholder – consensus has a huge impact on whether or not the sale will close
  • Find the insights that lead to the business’ best & unique strengths. Ideally, the insights that are currently undervalued by the customers.
  • Find the business best & unique strengths
  • Educate the sales department on industry news, trends, alternatives and insights
  • Help sales reps and customers to understand the value in numbers of fixing the problem

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