Sales Coaching Capability: How to create a team of performers by cloning the Challenger Sales Model?

Abhishikha Chatterjee
February 24, 2022
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February 24, 2022
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Sales coaching is transforming. 

Earlier, sales coaching was given on subject matters like negotiation, pipeline management, prospecting, cold calling, etc.

Today, coaching has transcended to the creation of top-performing sales reps-a holistic approach. 

A rep can disrupt the customer’s thought process and instill new ideas and POV.

To understand this better, consider the customer journey issue Gartner emphasizes:

's research indicates that customers are halfway, around 57%, into the purchase process before meeting a seller. This means, in the first meeting, the customer arrives with preconceived ideas about what they need, how much they’ll pay, and what features the product must be designed with.

The approach should introduce a rep who can challenge the pre-conceived ideas and teach the customer to perform the same job differently.

And which sales methodology can you remember when you need a top-performing rep to marry the traits of a challenging rep- A Challenger Sales Methodology.

Related: How to maintain a certain amount of constructive tension across the sale?

What is a Challenger Sales Model?

While scrolling through book recommendations on sales best practices for 2022, we landed on The Challenger Sale on Amazon by Mathew Dixon and Brent Adamson.

The book portrays a variety of sales representatives and their common traits. But as per the top performing results, the Challenger Sales Rep stood out and took a major lead in complex deals.

So here’s a glance at the five personality types explained briefly-

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.

A challenger sales rep is a seller who focuses on controlling, teaching, and tailoring a sales experience. The Challenger sales model is unique to cater to prospects without being a “go along get along” person. 

Why Should Sales Coaching Focus On The Challenger Reps?

Many companies can crack the sales landscape with a relationship builder and hard worker. 

But those sales rep profiles fail to stir up the environment. 

Hence, companies are inclining towards challenger reps because they can handle these situations:

  1. Complex Selling Situation- Not all products can be sold with 2-3 meetings and exchange of 4-5 emails. Unique engineered products take a lot of time to get accepted by buyers. Not just that, the sales team also needs to cut through biases and old relationships. Complex solutions in the healthcare industry need several proposals and interactions at the senior level to close the deal. But Challengers have a knack for such sales deals and glide through complex selling situations without losing sleep(or lose sleep maybe a little).
  1. Information on the internet- The high amount of information customers receive on the internet delays the meeting with sellers. Sellers meet and greet customers when they have decided to buy a particular product at a specific price. Only a challenger rep can pique the prospect at this stage–breaking the pre-conceived ideas and embedding a new viewpoint.
  1. Differentiation- Although explaining the cutthroat competition is meaningless, let us rephrase it- a company needs to survive, and it needs challengers to break through the market barriers and differentiate themselves. Challenger sellers prepare to stand out–their sales pitch is never the same for two customers.
  1. Explore new markets- Entering a new market or geography isn’t easy. Apart from the GTM strategy, organizations need high-performing sellers to break through the traditional barriers and competitors to establish a new business. Receiving acceptance and business in less time is only a challenger reps game.
  1. New product category- Just like the market, a new product can’t sell by itself. Apart from the right marketing strategy, sellers need to make the value proposition strong and establish the importance of the product. Again, challengers can handle new products in a lesser number of days.
  1. Need excitement- Which sales team doesn’t like excitement? You had a great last quarter and wished to see similar results again. That’s never the case. To search for the big sharks from the market, you must have a challenger mindset. 

How can sales coaching help in building an army of challenger reps?

After reading the benefits sales companies enjoy with a challenger rep, it’s obvious to have a few such candidates in your team. 

Investing in new sales reps is definitely an option, but that comes with a cost. 

But working on the skillset of your current representatives is a great way to start.

The simple solution to this problem is sales coaching.

Sales coaches can get started with the following tips:

1. Encourage challenger sale culture during coaching sessions


  • The book- “The Challenger Sale”
  • Success stories and examples of The Challenger Sale(you’ll find a few anecdotes in the book as well)
  • Examples from the military and defense services.
  • Movies with powerful portrayals of challenger sellers.

2. Sales coaching must emphasize on newcomers

Beginners are more accessible to train than seasoned veterans. 

Choosing to unlearn and learn something new can be a difficult choice. You should strike the rod when it's hot and target new salespeople or those who are just out of college.

Related: 7 Sales Coaching Questions That Sales Coaches Must Ask Their Sales Reps

3. Make Reps learn the art of taking control

Your sales coaching program must focus on two scenarios-

  • Pricing Discussion- Challenger representative does not agree to discounts, instead of pitching a value-based solution.
  • Decision Making- You must challenge the customer's thinking and force the customer to take a decision sooner, and avoid stalling the deal.

4. Help them in making data-driven decisions

A coach can make use of call recording or conversation intelligence software to help sellers learn the magic of data.

Using data, your reps will be able to offer

  • Valuable perspectives about the market
  • Details about industry problems and trends
  • Better alternative solutions
  • Data-backed consultation, reduce pitfalls, and issues on the way

5. Encourage working on call quality rather than call quantity

How can sales coaches improve the quality of the call?

  • Checking conversation intelligence tools that offer automated review and 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. 

If you are preparing for an executive buyer meeting, this will help- C-suite meeting guide.

6. Teach solutions-oriented sales to approach

The time has come to move your sales reps from a product-focused to a solution-focused approach.

Sales approaches that focus on prospects' needs have a higher chance of winning deals than those focusing on products.

Even though a rep is selling, they are solving a problem, and a solution is a problem paired with a product.

7. Utilize Reps Strengths And Outperforming Skills 

Sales coaching can also sharpen existing skills because a regular rep may also possess skills that turn out to be their best move.

And the best move is the biggest strength. 

Your negotiating skills, pricing discussion, product demonstration, product knowledge, and engagement are among them. 

One cannot win the best deals without launching the hidden arsenal.  

Sales coaches must not forget to improve strengths and the rep’s weaknesses. 

8. Coaching Can Help In Learning Storytelling- An X-Factor

To teach storytelling, sales coaches can leverage conversation intelligence again.

A sales coach can teach the specifics of storytelling. During the time spent polishing the improvement areas, they can recite and listen to the sellers’ stories. Sometimes sales coaches create stories based on their experiences and record them for sales representatives.

A coach can accelerate the coaching process by using a conversation intelligence tool. Coaches can store coaching sessions and story recordings. Coaches can listen to call recordings and filter down moments to determine whether the reps are using storytelling. 

We know that’s a lot of tasks for a sales coach. But to position yourself in the market, you must have an army of unique professionals. 

No rep can turn into a challenger rep instantly, but a few sales coaching sessions and conscious efforts can bring 1% progress every day. 

“Success is the product of daily habits—not once-in-a-lifetime transformations.”― James Clear, Atomic Habits
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