The Challenger Sales Method powered by AI: Turn conversations into conversions

It's important to approach sales techniques with a pinch of salt. Most sales techniques are just different ways to approach your prospects to help solve their pain points with a solution you might have.

We all know that no one technique works in every situation or helps you close deals all the time. And yet, given the increasing instant gratification mentality, there is always an obsession to find a magic bullet. 

The Challenger sales technique is one such controversial topic that either has great fans who swear by its results or staunch critics who dismiss it as yet another sales buzzword.

So what exactly is the hype about the Challenger sales? Does it make sense for anyone to adopt it, or is it for SDRs and AEs of a specific kind, like Type A salespeople? 

In this post, we will attempt to dive into the following:

• What is the Challenger sales technique?
• How is it different from other sales approaches?
• Using AI to improve and automate Challenger Sales implementation

What is the Challenger sales technique?

Challenger sales is a concept that originated from a book titled The Challenger Sale: How To Take Control of the Customer Conversation, written by Matt Dixon and Brent Adamson. Since its first release in 2011, Dixon and Adamson have promoted the Challenger Sale as a powerful approach for salespeople to lead sales conversations confidently.

Suppose I had to distill the book's wisdom in one line: The Challenger Sale is all about positioning yourself as an expert/authority figure to your prospects and taking control of the conversation. The idea is to thereby stay in control of the entire sales process.

Built around the idea of "teach, tailor, and take control," the book talks about the Challenger Sale as a tool to give customers information that they possibly can't learn on their own. The book suggests that the biggest competition that most sales teams face today isn't the rival product in the same category but the prospects' ability to find information on their own.

Therefore, the authors say that it's imperative for sales teams today to educate their prospects about what they don't know instead of regurgitating the sales copy on their company's website or asking clichéd questions like "what keeps you up all night?"

The book positions the Challenger Sale as an effective replacement for the other techniques by drawing parallels between different seller profiles:

1. The Relationship Builder: Good with building rapport, believes in the classic style of consultative selling

2. The Reactive Problem Solver: Responsible, reliable, and detail-oriented salesperson who will go the distance to solve problems

3. The Hard Worker: The Hollywood-styled salesperson with a never-say-die attitude who is also invested in personal development

4. The Lone Wolf: Highly instinctive, no-holds-barred kind of salesperson who is hard to manage but delivers desired results

5. the Challenger: Someone who does their homework, understands their prospects' problems, and doesn't hesitate to push the customers if need be

The Challenger profile sits at the heart of the Challenger Sales method. It represents a salesperson who combines a deep understanding of customer business challenges with the confidence to push back and introduce new ways of thinking. While every profile adds value, the Challenger stands out by actively teaching clients novel approaches, customizing messages to individual needs, and steering conversations, even around difficult topics like pricing.

According to the book, here are six attributes that set the Challenger reps apart:

• They offer their customers unique insights
• They have strong two-way communication skills
• They know the individual customer's value drivers
• They can identify economic drivers of the customer's business
• They are comfortable discussing money
• They can apply gentle but firm pressure on the customer

All in all, the idea is about disrupting your prospects' self-learning process by presenting them with valuable information that's hard for them to find on their own. The authors argue that the Challenger salespeople have an unparalleled advantage in controlling the sales conversation and offering a sales experience that extends to customer loyalty.

How the Challenger sales approach works in practice

Challenger Sales relies on three core principles: Teach, Tailor, and Take Control. 

Teach

‍Challenger salespeople offer unique insights that prospects may not have discovered on their own. Rather than rehashing existing product information, they deliver new, thought-provoking ideas that help the prospect understand latent challenges and opportunities in their business. This "teaching" establishes the salesperson as a trusted expert in the field.

Tailor

‍Understanding that every customer is unique, the Challenger approach emphasizes customizing the sales conversation based on the prospect’s specific business drivers and pain points. This tailored approach ensures that the conversation resonates personally with the customer, addressing both emotional and rational concerns.

Take Control

‍A critical element is the salesperson’s willingness to guide the conversation. This means confidently challenging the prospect’s preconceptions, even discussing topics like pricing or potential pitfalls, and applying gentle but firm pressure to steer the sales process toward a decision. By controlling the dialogue, the salesperson helps manage the buyer’s self-directed research and potential missteps.

Here’s an example of how the Challenger sales strategy might look like if you were to apply it in real-life:

Imagine that you are in the business of selling marketing automation software. You know for a fact that most of your prospects are always looking to automate their email outreach so that they can scale their lead generation efforts.

The prospects might think that they know what their needs are. But as an experienced practitioner of the Challenger Sale approach, you present them with data and facts that they are not aware of. This will earn you the respect of being an expert in the field.

You may challenge the prospect, "How will you personalize your email to people who visited your pricing page vs. someone who read one of your blogs?" You will then present a solution, i.e., your product, that solves this problem. Thus, you give your prospect a new way to engage their visitors in different stages of the buying cycle. 

How is the Challenger sales approach different from other sales approaches?

When it comes to picking a sales approach, there are many options for salespeople to choose from. Here are a few of the most popular ones:

Consultative selling

One of the most popular techniques among seasoned salespeople, consultative selling (sometimes known as value-based selling), prioritizes solving the customers' problems over selling the product. Genuinely advising prospects about the right solution helps salespeople differentiate themselves as trustworthy advisors rather than coming across as pushy salespeople.

Solutions selling

An extension of consultative selling, solutions selling is the process of asking the right questions to your prospects, actively listening to them, identifying their problems, and suggesting the best solution to fit their needs.

The buddy approach

The buddy approach of sales is a great fit for naturally friendly, outgoing salespeople who are good at building rapport with people. The buddy approach believes that people buy from people they like and trust, and their buying decisions are mostly based on emotions, even in the buttoned-up B2B domains.

The guru approach

On the opposite end of the spectrum from the buddy approach lies the Guru approach. It is a technique that believes in selling based on logic and rationality rather than feelings or emotions. The Guru approach requires you to present yourself as a thought leader or a subject matter expert in your given space.

Target account selling

Target account selling, also called account-based selling, is about identifying a few right customers who share a common pain point and selling them your solutions based on extensive research and analysis. In other words, target account selling focuses on quality rather than quantity.

SPIN selling

Based on Neil Rackham's book by the same name, SPIN selling is all about asking a set of tactical questions to lead the sales conversations confidently. These questions are based on the SPIN's full expansion, i.e., Situation, Problem, Implication, and Need.

Customer personality selling

Customer personality selling is our favorite because it's flexible and borrows its principles from other sales techniques to take an approach that suits the buyer. Instead of focusing on what type of sales approach is best for your company, customer personality selling encourages you to tailor your approach based on the customer type.

There are plenty of other sales techniques out there, which, frankly speaking, fall into one of the above approaches or go by different names while accomplishing the same goal. Now that you have a fair understanding of all sales techniques, you must be wondering…

How is the Challenger sales method different?

The Challenger Sales approach differs from traditional methods by focusing on teaching, tailoring, and taking control of sales conversations.

Unlike consultative or solution selling, which prioritizes uncovering needs, Challenger reps challenge customer assumptions, offering insights that reshape their thinking. 

While the buddy approach builds rapport and the guru approach emphasizes expertise, Challenger sales push prospects to reconsider their business strategies.

It also contrasts with SPIN selling, which relies on structured questions. Rather than adapting to customer preferences like personality-based selling, the Challenger method proactively leads discussions, making it highly effective for complex B2B sales where differentiation is key.

How effective is Challenger sales?

According to the book, while all salespeople fell into one of the five seller profiles mentioned above, 40% of all high sales performers across all industries applied the Challenger style of selling to close deals. 

Other stats in the book cite that high-performing sales reps were twice as likely to use the Challenger sales approach and 50% of all-star performers in the complex B2B sales environment fit the Challenger Sale profile.

With top analyst firms like Gartner endorsing the Challenger Sale’s efficacy in closing deals, there’s no doubt that the book authors have created a successful brand around the Challenger sales. 

Here are things to keep in mind when you implement a Challenger Sales approach:

Pre-implementation considerations

Customer fit assessment

Evaluate if the prospect is a good fit. If they aren't, disqualify them early, rather than trying to force the Challenger approach.

Sales team assessment

Assess the experience level of your sales team. Make sure they have the maturity to use the Challenger approach effectively.

Recognize that not all salespeople are natural "Challengers." Consider the personality differences among your reps (e.g., some might be better at building rapport).

Determine if you can coach everyone on your sales teams to be Challengers.

Organizational alignment

Plan for collaboration with other teams (Product, Marketing, Customer Success). Avoid a siloed sales approach.

Establish processes for sharing learnings from Challenger sales interactions across the organization.

During sales interactions

Balance teaching with listening

Avoid being overly preachy or assuming you know more than the customer.

Prioritize listening to understand the customer's perspective, especially with well-informed buyers.

Establish relevance before challenging.

Contextual awareness

Carefully read each situation. Avoid applying the Challenger approach forcefully or inappropriately.

Objection handling vs. challenging

Distinguish between pushing back when handling objections and challenging a customer's core assumptions.

Post-sale and continuous improvement

Knowledge transfer

Capture and analyze what you learn from sales conversations (think about using conversation intelligence tools).

Use data to identify areas where you can improve your sales process (e.g., which conversation stages need more focus).

Using AI to Improve Challenger Sales Implementation

It's true that the Challenger sales approach is effective and proven. Still, many leaders hesitate to implement it because it is complex and tricky.

For example, one of the challenges is that the rep should be confident but not overly pushy. How can managers and leaders monitor this? It is nearly impossible for them to watch all the sales calls.

This is where AI can help. It can simplify your Challenger Sales implementation by streamlining every stage of your process. AI tools can help your team focus on high-impact activities with clear, data-driven insights, from identifying ideal customers to refining sales messaging and analyzing performance.

Let's look at how you can use AI to make Challenger implementation easier for your team.

1. Prospect identification

AI can identify ideal customers by analyzing CRM data, emails, website visits, and social media activity. Using techniques like machine learning and natural language processing, AI can detect the different customer archetypes from the Challenger Sales framework:

Customer archetypes and AI methods

• Mobilizer
  Drives change, builds consensus, champions results, and asks probing questions.
  AI can spot mobilizers by:
  
  • Examining collaborative language (using "we" vs. "I")
  • Tracking engagement with insightful content
  • Analyzing sentiment toward innovation
  • Mapping network centrality within organizations
• Talker
  Shares information but may lack influence for change.
  AI can identify talkers by:
  
  • Monitoring communication volume and response patterns
  • Noting a focus on personal rather than collective language
  • Observing limited questions about organizational impact
• Blocker
  Resists change and hinders progress.
  AI can detect blockers by:
  
  • Measuring low engagement and infrequent communication
  • Sensing negative sentiment toward new ideas
  • Identifying minimal participation in discussions

2. Tailoring sales messaging and content

AI can personalize your sales engagement by using customer data to tailor messages and content that speak directly to individual needs. This stage supports the Challenger Sales “Tailor” principle:

• Customized Outreach
  AI can help craft personalized emails, scripts, and presentations using natural language generation. It adjusts tone and content for different platforms such as email, LinkedIn, and calls.
  
  
• Automated Follow-ups
  AI-powered chatbots can handle routine follow-ups, ensuring timely communication with prospects.
  
  
• Content Recommendations
  By analyzing customer interactions, AI can suggest relevant case studies, whitepapers, or additional content to keep your messaging on point.

3. Analyzing sales conversations

AI can transform your sales interactions by analyzing call recordings and email exchanges. This analysis provides actionable insights into how effectively your team applies Challenger techniques:

• Transcription and Categorization
  AI can transcribe conversations and identify key topics and questions asked.

• Performance Metrics
  By measuring talk-to-listen ratios and sentiment, AI highlights areas where sales reps excel or need improvement.

• Feedback for Coaching
  Detailed analysis of sentiment and call patterns helps identify best practices and common pitfalls, enabling targeted coaching.

4. Implementing Challenger templates and scorecards

AI can support the implementation of your Challenger Sales templates by ensuring adherence to defined strategies and tracking performance with robust scorecards. This integration helps your team consistently apply best practices and fine-tune their approach, leading to improved performance over time.

Template integration

‍Meeting templates help standardize and streamline meeting workflows. They allow you to quickly set up meeting agendas, notes, and follow-up items, ensuring consistency across your team. By using templates, your reps can save time, reduce manual work, and ensure that critical topics and questions related to the Challenger method are always covered during meetings. This consistency supports effective coaching and improved meeting outcomes, as everyone follows the same structure and best practices.

Example Challenger Sales meeting agenda template for B2B software (Avoma) 

1. Opening (Set the Stage)

• "Thanks for taking the time today. Before we dive in, I’d love to learn more about your current process for capturing and using customer conversations. Does that sound good?"
  
• "We work with a lot of sales and customer success teams, and I noticed [specific challenge from prior research]. We can discuss ways to make that process more efficient today."
  

2. Personalized Teaching Moment (Disruptive Insight)

• Challenge the status quo:
  
  • "Most sales teams think they have good visibility into deal risks, but research shows that 60% of lost deals happen due to a lack of multi-threading and follow-ups that don’t address the right objections."
    
  • "A lot of teams rely on manual note-taking and CRM updates, but studies show that reps spend 20-30% of their time on admin work instead of selling."
    
  • "Coaching often happens too late—many teams don’t spot patterns until the end of the quarter, missing early signs of deal risks."
    

3. Tailored Messaging (Connecting to Their Pain Points)

• "From what I understand, your team spends a lot of time manually documenting customer interactions. With Avoma, you can automate note-taking and CRM updates so your reps stay focused on selling."
  
• "You mentioned that coaching is a challenge because you’re unsure what’s happening in real-time. AI-powered conversation intelligence lets managers pinpoint where deals go wrong and coach proactively."
  
• "It sounds like your forecasting is based on subjective inputs. AI can objectively analyze customer sentiment, engagement, and past deal patterns to improve accuracy."
  

4. Guided Discussion (Probing Questions to Challenge Thinking)

• "How do you currently track engagement levels in deals? How do you know if you’re multi-threaded enough?"
  
• "What happens when a key stakeholder suddenly disengages? Do you have a way to detect that early?"
  
• "If your team could free up 5+ hours per rep each week, what would they focus on instead?"
  
• "What’s your biggest challenge in ensuring reps follow up with the right messaging at the right time?"
  

5. Next Steps (Clear Actions and Follow-ups)

• "Based on our discussion, it sounds like [main challenge] is a top priority. Let’s schedule a follow-up session to dive deeper into how Avoma can help."
  
• "I’ll send over a recap with specific insights on how teams like yours have solved this problem."
  
• "Would it make sense to set up a session with [decision-maker] to walk through how AI-powered insights can improve deal visibility?"
  

Scorecard Insights

AI-powered scorecards can be pre-built for methodologies like Challenger, MEDDIC, and Sandler. They offer:

• Customized criteria that track the effectiveness of your sales interactions
• AI-generated justifications for scores so both managers and reps understand what contributed to each score

5. AI co-pilot to extract key details

Your sales reps can use AI co-pilot and questions to analyze past interactions and surface key topics, objections, and stakeholder engagement history.

Challenger sales made easy with AI

Challenger sales turns every conversation into a clear, data-driven dialogue. 

With Avoma, you take a smarter way to sell by automating note-taking, tailoring messages on the fly, and tracking your progress with dynamic scorecards. Imagine having an AI tool that not only streamlines your sales process but also offers real-time analysis, helping you pinpoint where your strategy shines and where it needs a tweak. 

This means you can confidently teach, tailor, and take control of every interaction without the usual hassle.

Plus, with Avoma’s easy-to-use scorecards, monitoring your team’s performance becomes second nature. 

Simplify your sales approach and boost your results. Try Avoma for free or schedule a demo today and experience firsthand how AI can turn complex sales challenges into simple, actionable steps.