10 Challenger Sales Best Practices: How to maintain a certain amount of constructive tension across the sale?

9 min readJan 20, 2022
Who needs a laptop, I can do wonders with a cup of tea- The Challenger Rep

While scrolling through book recommendations on sales best practices for 2022, I landed on The Challenger Sale on Amazon.

I wasn’t sure what I’d achieve from reading the book that portrays types of sales representatives.

However, by the first two chapters, I was sure this book, written by Mathew Dixon and Brent Adamson, may change how you and I think about sellers or, shall I say, types of sellers.

Sales best practices can’t be categorized under a single sales rep profile.

Story Time:

Once a sales coach tried convincing a sales rep to participate in a sales coaching discussion on negotiation. The rep didn’t deny coming for the session. Her only argument was, why do you think I need a negotiation session?

Is it what you think I need to improve, or do you merely want to coach me on the topic? The coach found himself caught off guard, and worse of all, he didn’t even have access to a call recording software’s support to prove anything.

What do you think about the rep’s personality?

You’d be surprised to see the versatility of the sales rep and how they transform the sales landscape.

Today, I’d like to discuss only one personality- The Challenger seller.

And, you can Google them up and read for yourself what the challenger seller is and what they do.

What is a Challenger Rep? By Gartner

My inspiration from the book has led me to write for sales managers trying to build a team of sellers with the same profile.

Let’s help you build a team of challenger sellers by applying the best of sales best practices in the year 2022.

Table of Content

  • What sales best practices can be learned from different TYPES OF SELLERS?
  • Why are we discussing the CHALLENGER SELLER and their sales best practices?
  • What are the 3 PILLARS(sales best practices) of a successful challenger selling model?
  • 10 essential CHANGES to become a challenger sales rep | Best Practices

Although we decided not to bore you with the what and why that’s unfair for someone who hasn’t come close to reading the book or hearing about it.

Others can skip to the good part- 10 essential changes…

What sales best practices can be learned from different TYPES OF SELLERS?

In any sales environment, you’ll find sellers who generally fall in five different categories or, let’s say, sales rep personality types.

These five types of sales reps-

  • Determine the style of selling a product or service.
  • Determine their relationship with the organization and customers.
  • Determine how one company differentiates from another.

So here’s a quick glance at the five personality types explained most simply and effectively-

The Hard Worker -Nose to the grindstone sellers- Come early, stay late.

The Lone Wolf-Cowboys nailing numbers while driving the sales leaders crazy

Problem Solver-Customer Service executive in the body of a salesman.

Relationship Builder-The 2 am friend, clients can count on. ( I’ll be there for you…)

Challenger-If we’re discussing them specifically in today’s article, they’re definitely unique.

So you get it, right?

If you like to get into details without wasting too much time about each rep’s profile, then this image should do the magic-

The five personality types of B2B sales professionals

Why are we discussing the CHALLENGER SELLER and their sales best practices?

So, moving on.

As discussed before, we are particularly interested in the Challenger sales rep. Why? What’s so extraordinary about the Challengers and their best practices.

Well, if I tell you they have the capability of declining to bid to an RFP and help in building the RFP themselves?


What if I told you that they’d not let the prospect talk about pricing until they think the prospect is ready for the pricing discussion.

Getting the feels?

In simple terms, the challenger sellers don’t follow the norms or rule book. They challenge it and tweak it as per the requirement.

Challengers don’t have a single pattern or method to work; they can adapt the new and accept the old as and when needed.

If you are or know someone in your team who’s giving you a hard time by challenging you on everything that’s been there or done, well, that’s your challenger.

What are the 3 PILLARS(sales best practices) of a successful challenger selling model?

Without stretching much on who and what is a challenger(there’s so much data on the Internet), let’s shift our focus to a critical aspect that challenger reps follow fearlessly- the three pillars of the Challenger Selling Model

Adapted from the Challenger Sale book

These three pillars are the defining attributes of a sales guy.

In the rest of the article, you’ll be building these three attributes with the help of the ten essential changes required in your team.

10 essential CHANGES to become a challenger sales rep | Best practices

Are you the sales manager?

Do you wish to see significant changes in your reps’ performance and beef up your overall business?

You should implement a few sales best practices within your team and help them emulate a challenger seller.

  1. Encourage challenger sale culture in the team

Change begins with culture, and culture is the sales leaders’ responsibility.

You get to transform your team with the help of different mediums and activities. A few tried and tested methods are listed for you:

  • Make your team read the book- “The Challenger Sale”
  • Introduce success stories and examples of The Challenger Sale(you’ll find a few anecdotes in the book as well)
  • Take inspiring examples from the Army and defense services.
  • Watch powerful movies that portray the character of the challenger seller.

2. Train the newcomers and newbies first

Haven’t we all heard of the beginner’s mindset?

It’s easier to train a beginner than a learned veteran.

Unlearning and learning something new can be a tough choice. Try to strike the rod when it’s hot- target the newbies- new sales guys or sales guys fresh out of college.

3. Make reps learn to take control of the sales meeting

Promoting challenger sales means you are encouraging a vital sales best practice which is generally difficult to conquer- controlling and manipulating the meeting.

There are two scenarios the challengers control assertively-

a. Pricing and money discussion- Challenger rep doesn’t agree for discounts rather pitch a solution that sells on value.

b. Decision-making cycle- Challenge customers’ thinking and force the customer’s decision-making cycle to expedite the decision rather than delay or stall the deal altogether.

4. Like customers, challenge senior leaders(including YOU!)

What’s the point of challenging the rest of the world when you can’t challenge the people at your home.

Challengers are innovative and creative. Their mind is always scavenging for new ideas and problem areas. This nature of challengers makes them break the norms and try something new.

To try “something new,” you must challenge yourself, the organization, and the senior leaders who created the rules.

Bending the methods and tweaking requires the rep to develop fresh ideas and back their arguments with data.

5. Stop believing in intuitions and make data-driven moves

Now, that we’ve hit the cord and spoken about data, let’s directly drive the discussion to how challengers use insights to navigate sales meetings, especially with C-suite executives.

Intuition and guesswork can take you far for a while. Afterward, the magic lies in the hands of data.

With the help of data, your reps will be able to-

a. Offer valuable perspectives on the market

b. Offer education on industry problems and trends

c. Offer better alternatives

d. Offer data-backed consultation

e. Reduce pitfalls and issues on the way

6. Focus on call quality rather than call quantity

While pipelines are your best bet to close more deals, don’t run behind too many calls in a week or day.

Prioritize and attack!

Choose meaningful and quality meetings and then start working on the quality of the meeting.

How can you improve the quality of your call?

  • Investing in conversation intelligence tools that offer automated feedback using AI.
  • Preparing in advance and understanding the ICP.
  • Researching well and taking extra efforts for C-suite execs or final closure calls.
  • Participating in mock calls.
  • Conducting regular sales coaching sessions

7. Have a solutions-oriented sales approach

If your reps are focusing on a product-led sales approach then it’s time to shift them to a solution-led sales approach.

The sales approach that focuses on prospects’ needs has a higher chance of winning deals than one that focuses on products.

Customers are humans, and they care about their pains as much as you do. Solution selling is exactly what the customer wants.

Even though you’re selling, you are solving a problem, and a problem married to a product is what a solution entails. Simple. Case closed.

8. Work on delivering customer value than customer convenience


A rep couldn’t fit into the customer’s problem. The rep clearly understood what the customer needed. He guided them through the situation and asked to meet up with three vendors who could solve the problem(1 was a direct competitor).

The features needed by the customer were clearly not available in the rep’s brand, and the rep was honest about it.

Seeing the value and efforts of the rep in guiding the prospect to the right audience. The prospect made an offer- Can your company build the features at the same price while we stay flexible with the timelines?

The story explains what value can do to a prospect.

9. Leverage strength that outperforms peers/competition

You are a regular rep but the best sales practices have always said- slay with your best move.

And what’s your best move?

Your best move is your biggest strength.

It could be your negotiating skills, pricing discussion, product demonstration, product knowledge, and engagement, to name a few.

Without launching your arsenal, you can’t imagine winning the best deals.

While you improve your weaknesses, don’t forget to sharpen your strengths.

10. Be a conversation winner and excellent storyteller

Source: Tim Denning

Conversations navigated through stories are better memorized and remembered by people.

In fact, as per a psychologist- Jerome Bruner’s- one can remember facts 20 times more if included in a story.

So, you must encourage creative thinking investing in customer success stories, and get in touch with customer success teams to get a better view of the current clientele.

Hang on Sales Managers. We’re not finished yet

To encourage your team to adopt the style and life of a challenger seller, there are a few responsibilities on your shoulder as a sales manager.

There are three high-level attributes that you must build to become an excellent manager:

Attributes affecting frontline Sales Manager Performance, The Challenger Sales

Now that you have gone through the article, we’re sure you are ready to start your team’s journey on the path of The Challenger Seller.

If you feel there are hurdles on the way, take feedback from your reps and clients on the new sales strategy. You can also take advantage of a call recording or sales tracking software to see how effectively your reps leverage the challenger rep sales best practices.

And if this particular piece has piqued your interest a little bit? You’ll love the sales best practices categorically written for sales reps in 2022. — You won’t regret it!




I’m a marketer with over 4 years of content writing experience. Currently, I’m on a mission to create content that helps sellers overcome obstacles.