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Master the Art of the Challenger Sales Methodology

Posted in: Sales and Marketing Management, Sales Enablement Strategy

Sales reps who guide sales and educate prospects often outperform those focused on relationship building. 

Dive into the Challenger method with hands-on roleplay. It’s about rising above the noise, teaching effectively, and guiding customers through their journey.

What is the Challenger Selling Methodology?

Matthew Dixon and Brent Adamson developed the Challenger Sales Methodology. It relies on sales training to empower sales reps to teach, tailor, and take control of conversations. Instead of echoing what prospects want to hear, this approach challenges customers’ existing viewpoints to add actual value.

Different Types of Sales Reps According to Challenger

When considering the Challenger Sales Model, it’s worth noting that 40% of top performers adopt this approach. This Gartner data highlights its effectiveness and popularity in B2B sales. Before we dive into what makes a Challenger rep, it’s helpful to understand other types of sales reps.

Hard Worker

Hard workers are the salespeople who go the extra mile, making more calls and sending more emails than anyone else. They’re diligent but often stuck in old, dated methods.

Relationship Builder

The relationship builder aims to become everyone’s best friend. They’re excellent at providing a smooth-sailing sales experience and maintaining existing accounts but sometimes struggle to challenge customers and close new deals.

Lone Wolf

Lone wolves follow their gut and often ignore the sales playbook. Lone Wolves can be high-performing but are hard to manage.

Problem Solver

Problem solvers are reliable and thorough. They are great at post-sale service. However, they get mired in the details and can take a long time to close deals.


Challenger reps are self-motivated individuals who aren’t afraid to challenge the status quo. They use their deep understanding of a prospect’s business to push their thinking.

The Challenger sales rep encourages discussion, educates prospects, and introduces alternative viewpoints. Key attributes contributing to their success include:

  • Bringing fresh ideas to the table
  • Mastering the art of give-and-take communication
  • Understanding what truly matters to each customer
  • Recognising the financial factors driving a customer’s business
  • Being at ease when talking about finances and pricing
  • Capable of assertively nudging the customer

Dixon and Adamson later discovered that they could group these traits into three core capabilities, or the three T’s of the Challenger sale, which they argue encapsulate the spirit of a Challenger.

Three T’s of the Challenger Sale

The top sales reps are more than order takers; they shine as challengers. A Challenger sales rep excels in three core areas, often called the “Three T’s.” These skill sets distinguish them as top performers in complex sales processes.

Challenger sales reps excel in:

  • Teaching: They offer valuable insights that may never have crossed a customer’s mind.
  • Tailoring: They customise their sales messages to customers’ needs and concerns.
  • Taking control: They’re not afraid to assert themselves, steering the conversation without being aggressive.

How to Implement the Challenger Sales Model

To integrate the Challenger Sales approach into your sales playbook, sales reps need to acquire a new skill set. This integration requires targeted sales enablement training to arm them with the six essential Challenger strategies. 

When applied, salespeople don’t just make the sales pitch more compelling; they inspire conversations and reshape beliefs. Below are six sales strategy components and sample questions designed to push the envelope, challenge the status quo, and guide your discussions in a direction that truly matters.

  1. The Warmer: Build credibility by showing you understand the prospect’s world. Ask the prospect, “Can you share some of the biggest pain points you currently face?”
  2. The Reframe: Challenge their assumptions with insights they haven’t considered. Ask the prospect, “Have you ever considered [Insert Idea] as a way to tackle [Problem/Area of Concern]?”
  3. Rational Drowning: Use data, customer success, and logic to highlight the importance of acting now. Ask the prospect, “How would it impact your bottom line if you could solve [Challenge] by [Percentage]?”
  4. Emotional Impact: Make it personal; hit the emotional chords that drive action. Ask the prospect, “How does [Challenge] personally affect you and your team’s daily work?”
  5. A New Way: Introduce a solution that addresses their newly discovered needs. Ask the prospect, “What if I told you there’s a different way to address [Challenge] that you might not have considered?”
  6. Your Solution: Naturally, show how your product or service is the best fit. Ask the prospect, “Have you tried [Solution Category] to address [Challenge]?

What Makes the Challenger Sales Model Stand Out

The Challenger Sales Method is more than just another sales methodology—it’s a game-changing approach designed to meet today’s complex selling landscape. Unlike traditional sales models, Challenger selling equips you with the tools and techniques to navigate sophisticated client interactions.

Brent Adamson, the Distinguished Vice President of Advisory at Gartner and co-author of “The Challenger Sale,” says, “Sales organisations can increase business by challenging customers — delivering customer interactions specifically designed to disrupt their current thinking and teach them something new. It’s not just about selling something anymore.” Adding weight to this point, 60% of salespeople earning $250K or more use the Challenger Sales Methodology, emphasising its effectiveness for top earners.

What sets the Challenger Model apart from other sales methodologies? The Challenger model leads to: 

  • Reduced sales cycles: The methodology focuses on direct, insightful conversations that quickly reach the heart of the customer’s needs. This can considerably shorten the sales cycle, saving time and resources.
  • Increased revenue: The Challenger Sales Model has been shown to significantly boost revenue by driving higher deal sizes and improving win rates
  • Improved cross-sell opportunities: The value-based relationships built through this model often open doors for additional revenue streams, including cross-selling and upselling, thereby increasing the lifetime value of each customer.
  • Optimised sales training and coaching: The Challenger approach offers a structured training framework, enabling organisations to improve sales performance. It provides a clear path for ongoing sales enablement, learning, and skill enhancement, ensuring your star performers stay ahead of the curve.

How to Turn Your Sales Team Into Challengers

Transforming your sales team into Challengers starts with a robust training programme. You’ll want to focus on three things: teaching your team to educate customers, tailor messages, and take control of the sales conversation. The idea is to make your reps not just sellers but also trusted advisors. 

Coaching a Hard Worker

Teach the hard worker to leverage their work ethic in learning about the customer’s business, not just in outreach volume.

Coaching a Relationship Builder

Encourage relationship builders to use those excellent interpersonal skills to challenge clients, not just to maintain rapport and customer loyalty.

Coaching a Lone Wolf

Get lone wolves to channel their independent streak into crafting unique perspectives and compelling customer solutions.

Coaching a Problem Solver

Help problem solvers focus on preemptive problem-solving and value propositions to close deals rather than post-sales troubleshooting.

Challenger Sales Roleplaying

One way to build Challenger skills is to take sales teams out of their comfort zone and roleplay with sales leaders. Have sales reps practise scenarios that align with the ‘three T’s,’ teaching, tailoring messages, and taking control of the customer conversation.

Challenger sales method roleplaying allows you to put theory into practice. For example:

  • Teaching roleplay: The sales rep explains new insights on an industry trend the prospect is likely unaware of and how it impacts their business.
  • Tailoring roleplay: The sales rep responds to a standard objection by linking it back to something specific the prospect mentioned earlier.
  • Taking control roleplay: The sales rep redirects prospect conversations by returning them to a critical insight.

Through roleplaying, sales management and salespeople can collaborate to learn about Challenger Selling—and by doing it. This hands-on approach is the quickest route from understanding the challenger sales approach to mastering it.

Does the Challenger Sales Methodology Suit Your Team?

The numbers say it all: more than half of the best salespeople use the Challenger method, especially when dealing with sharp stakeholders and complicated sales. So, it’s worth considering the Challenger Sales Methodology if you’re in a similar situation.

However, the Challenger Sales Methodology may not be for everyone. Implementing the sales model requires a level of skill that might be too complicated for some sales teams. It’s not just about being a good salesperson; it’s about having the ability to teach, tailor, and take control of customer interactions. This means that sales professionals must have a profound understanding of the product they are selling and the customer’s business, along with the skill to disrupt traditional thought processes positively. 

It’s worth noting that other sales methodologies, such as the Sandler Selling System, offer alternative approaches. While Challenger focuses on teaching, tailoring, and taking control, Sandler emphasises a consultative selling technique. If your team excels in empathetic questioning and relationship-building, the Sandler method may align more closely with your strengths. On the other hand, if you’re dealing with educated decision-makers in complex selling environments, the Challenger approach could be more suitable.

Let Highspot Help You Develop Challenger Sales Reps

In today’s competitive sales environment, prospects come prepared and expect more than just a product. They are looking for meaningful conversations and tailored solutions. This is where the Challenger Sales Methodology comes in, empowering you to challenge, educate, and add value to every prospect conversation. But understanding these principles is only half the battle—you must master them.

Highspot’s robust training programme can help transform your sales reps into true Challengers. We equip them to transition from mere product pushers to trusted advisors capable of navigating today’s most complex sales scenarios.

Andee Harris, CEO of Challenger, couldn’t have put it better:

“Highspot is an invaluable resource for sellers. Combining Highspot with Challenger solutions, we’re bringing together the best of breed to make training, skills, and coaching seamless for reps to access.”

Let Highspot help you create Challenger sales reps who master the art of complex sales conversations. Request a demo of Highspot today.