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The Challenger Sales Methodology: Is It Right For You?

Marissa Taffer|Updated Jul 2, 2023
two chess pieces on a chess board

Choosing a sales methodology for your organization can be a big task. There are many factors to consider including the type of product or service you’re selling, the type of clients you’re selling to, and even outside factors like the competition you face and the economy.

In this article, we’re focusing on the Challenger Sales methodology, what it is, how to implement it in your organization, and some great questions that challenger sellers should be asking their prospects to gain the insights they need to move deals forward.

One of the most interesting things about this methodology is that it is relatively new compared to some other enterprise sales methodologies, with the research that launched the method being completed in 2008.

In the great recession, why are some sales reps still crushing their quota while others struggle?

This is the question that Gartner researchers Matthew Dixon and Brent Adamson set out to solve. They noticed that although the economy was struggling and the US was in a recession, some sales professionals were star performers and still absolutely crushing their quotas.

They asked themselves who these reps were and why they were able to be so successful with the economy working against them and many organizations looking to downsize and cut costs. And then they got to work studying how many sellers did their jobs.

Through their research and analyzing the work of thousands of sales professionals, they found that salespeople fell into five main profiles:

  1. The hard worker - This type of rep worked SO hard to achieve their targets. Any challenge put in front of them, they’d solve by working harder. They are self motivated, detail oriented and always go the extra mile (or twenty) to close the deal.
  2. The lone wolf - The lone wolf is the type of rep who, for better or worse, goes off on their own and does sales their way. They are confident and self assured and don’t feel like they need to follow the rules (or SOPs).
  3. The relationship builder - The relationship builder focuses on getting to know their potential customers and uses the power of the relationship to close the deal. Their relationship building skills are second to none. Within a few meetings, they know everything about their prospective customers, including the names of all of their children or where they're enrolling in college.
  4. The problem solver - The problem solver is sometimes described as a customer service representative disguised as a salesperson. This person listens to the prospect’s problems and does everything in their power to solve them.
  5. The challenger - The challenger is someone who uses a deep understanding of the customer’s challenges to drive the sales conversation the way they want it to go. They aren’t afraid of deviating from the status quo and challenging (pun intended) their prospective customers to think differently.

They found that of the highest-performing sales reps in enterprise sales, over 50% fell under the challenger profile. What was most exciting to them in their research around these types of sales reps was that while some people were naturally challengers, the skills and attributes of a challenger could actually be trained and developed broadly.

What is the Challenger Sales Methodology?

The challenger sales methodology hinges on teaching, tailoring, and taking control of the sales process.

Challenger messaging involves identifying a challenge or problem that your prospective customer may or may not know they have. Then, you’ll show them how not solving the problem is costing them big. Finally, you’ll show them the way to solve their problem, and if you’ve done your job right, its a something that your product or solution (and only your product or solution) can solve.

In the book The Challenger Sale, the authors, Brent Adamson and Matt Dixon, share an example from Grainger. In the example, the reps from Grainger can illustrate that unplanned purchases for their customer cost a lot of money. Not only does the part need to be purchased, but having staff members go to the store and look for parts is expensive.

The sales reps showed how sending a staff member out to buy a hammer plus the cost of the hammer came out to $50 (and this was years ago — imagine what inflation has done to the cost of the hammer). But, if this customer were to hire Grainger as a supplier, they could take advantage of a vast network of warehouses and inventory, leading to a decrease in unplanned purchases and a lot of time and money saved.

How to implement a “challenger” first approach in your sales process

There are a lot of reasons why companies in b2b sales environments should consider implementing the challenger sales model today. According to Challenger Performance Optimization, Inc., Challengers:

So, how should organizations implement the challenger model and set their sales teams up for success?

Understand how the process works

When taking a prospect through a challenger conversation, there is a six-step choreography that sales reps should follow to allow them to take control of the customer conversation. The first step in implementing Challenger in your organization is teaching the choreography to reps as well as sales management.

The choreography of a challenger conversation goes like this:

The Warmer - This is the warm-up to the conversation. In this early part of the choreography, the sales rep sets the stage and establishes some credibility. They’re demonstrating empathy but also showing that they understand the customer’s business or industry at large. This is all to build up to the reframe.

The Reframe - In the reframe, the rep is taking the problem or pain point that the customer is trying to solve and starting to frame it in a new way. The purpose of this reframe is to provide a new perspective and shift the customer’s thinking.

Rational Drowning - Once the new perspective has been introduced, the sales rep uses rational drowning to demonstrate the scope of the issue and the consequences of not taking action. Remember, this is still not the sales pitch, so the product or service should not even have been brought into the conversation yet.

Emotional Impact - Now that the potential customer understands that they have an issue and that there are real consequences for not taking action, the sales rep should be personalizing the problem and really emphasizing the consequences of keeping the status quo or not taking action to remedy the problem. At this point in the conversation, the prospective customer may have some strong emotions, but that’s okay. The conversation is about to take a turn...

The New Way Forward - Now that the prospective client is emotionally charged, the sales rep will start to turn the conversation to solutions to the problem. This still isn’t where we bring up the product or service. At this point, the rep is laying the groundwork for the solution, which will point directly back to the product or service.

Present the solution - Finally, now that the groundwork has been laid, the sales rep can start to present their solution to the customer’s problem. The product or service should be framed as the only solution to the challenge at hand. And this should be easier if we’ve followed the choreography correctly.

In the new way forward, we set the stage for this particular solution, so it should not surprise the customer. It’s important that the sales rep is driving the part of the conversation to focus on the unique solution and how it will work for the customer as opposed to focusing on features and benefits or, worse, price.

This choreography happens organically over a series of conversations. Top performers are able to guide prospects seamlessly through this choreography over the course of many conversations throughout the sales cycle.

They provide new insights throughout the sales experience and highlight the unique value proposition of the product or service that they provide in a way that appeals to a broad group of stakeholders in the customer organization.

Brainstorm differentiators

The challenger methodology relies on having commercial insights or differentiators that lead to your product or service and only your product or service. So, when reps learn about the challenger methodology, they’re excited by it but looking for those insights.

To shorten the learning curve, it can be helpful to create a playbook of insights and messaging that sales reps can use when taking prospects through the challenger conversation choreography.

These insights are best developed through teams of salespeople, marketers, and operations professionals. By combining these three roles’ skill sets, the messaging that is created will be polished and resonate with potential customers.

Like providing sales training, creating these messages should be an ongoing part of your sales strategy in a challenger organization. As industry trends shift and teams go through a few sales cycles, learnings should be incorporated into creating new messaging to help sales reps close deals.

Sales leaders can act as coaches, helping sales reps and their teams create messaging, integrate case studies, and provide a unique perspective to the key differentiators that can help their teams win in a competitive market.

Provide continuous training and reinforcement

As with any new skill you want to implement in your organization, challenger selling requires continuous opportunities to learn and improve. These opportunities can be formal classroom training as well as informal reinforcement over the course of doing business.

This could look like asking sales reps what is working and what they are struggling with in their challenger conversations and sales presentations with customers. It could also mean having your best salespeople sharing their most effective challenger messaging with new or struggling reps who need additional help.

It could also mean sales leaders attend meetings, and presentations and listen to calls and demos to coach sales reps in delivering their messages using the challenger sales approach.

In order for challenger to stick in your organization, develop a culture where the methodology is pervasive, and everyone from senior leaders to your newest reps is integrating the method into all of their sales activities.

Effective Challenger Sales Questions To Use

While a challenger is meant to take control of the conversation, that doesn’t mean that challengers don’t ask questions or listen actively to their prospects.

In fact, challengers can use good questions to guide their conversations and tailor their solution so that it is the only way the customer can move forward and solve their business challenge or address their pain point (whether they knew they had it or not).

Can you tell me how [operational area or line of business] and [specific process or function] work in your organization?

Early in the process, in what would typically be a discovery call or introductory meeting, the challenger is trying to get the lay of the land so that they can tailor a solution and take control of the sales process by asking discovery questions.

So, asking a prospect to walk them through a specific area of the prospect’s operation and processes that the organization uses is not a bad way to start!

As the prospect is describing the organization and processes, the challenger is listening for who is involved, what happens, and where the process might not be running as efficiently or profitably as it could be.

Getting all of this information might require asking some smart follow-up questions to guide the conversation and give the sales rep as much information as they need to move through the rest of the choreography.

Who is responsible for [process or operation], and who else is involved or impacted?

While this question may seem very similar to the first question, it gets more deeply at who is involved in the process AND who might be involved in the buying decisions when it comes to that point.

A challenger will be trying to take a mental (or physical) note of everyone involved so they can plan to engage them all appropriately throughout the sales process. In b2b sales, there could be more than seven people involved in making a buying decision. While not all of them have the power to green-light a deal alone, knowing who can say yes and who can say no and stall a deal is critical.

This is why the second part of the question about others who are involved or impacted is so important. Challengers want to make sure they’re engaging all of the key stakeholders in the right way, and leaving out someone’s needs or priorities can have dire consequences.

What percentage of your operating budget is currently allocated to [area they are looking to improve], and do you feel that is an adequate number to solve your challenges?

The way a prospect answers this question can tell a challenger a few things. First, how much of a priority the issue is (assuming they know this is an issue that can be addressed), and second how the prospect feels about the current allocation or priority.

If the number is low, but the prospect says this is a high priority, this is an opportunity for a challenger to show the prospect a new way forward. They will need to address the impact of their solution and why it is imperative that the prospect act now.

Suppose the prospect says that a large percentage of the budget is already allocated to this area. In that case, the challenger will simply need to show how a change to the status quo can have a big impact (and potentially save time or provide additional return on an investment that is already being made).

Have you ever considered...?

This is a great question when challenging the status quo and gauging how receptive a prospect is to a new way forward. This question can be paired with “Imagine... and describing the fully implemented solution that a challenger proposes.

If the prospect states that not only have they considered that solution or a similar one, the challenger can dig into what happened in a previous attempt and control the narrative by explaining how their solution differs or builds on what was attempted previously.

Are you frustrated by X?

Emotional words like frustrated are great to use when working through the emotional impact section of the choreography. Getting a prospect to admit frustration (or any other strong emotion) can highlight the need for change, and then the challenger can start to describe the new way forward, away from these strong and difficult emotions.

One thing to be careful of here is not to embarrass the prospect or point fingers. No one wants to feel like it’s their fault a system or process is broken, and if the conversation does start to shift in that way, a prospect may shut down. Having empathy and teaching from a place of wanting to support your prospects will help ensure this doesn’t happen.

Are you open to [insert the next step in your sales process]?

This question gives a sales rep insight into how they are positioned after the proposal. If the prospective customer is willing to commit to taking the next step in the sales process, there is a good chance that they are interested in moving forward with your proposed solution.

Depending on when the rep asks this question, the next step might be doing a test run, gathering more data or even closing the deal. A rep may want to ask this question (or a similar one) a few times throughout the sales process to ensure that the prospect is still engaging. Silence can be an answer, but it’s better when sales reps don’t have to guess what a prospect is thinking so that they are the ones driving the sales process.

Looking to explore Challenger right away? Get started with Qwilr’s Challenger Sales proposal template.


Is challenger sales still relevant?

Yes, the challenger sales methodology is still relevant today. In fact, one might argue that in this economic climate, the methodology is as relevant as it was when the original research was conducted in 2008. Additional research from the team behind the Challenger Sale was published in The Effortless Experience and The Challenger Customer.

What is a powerful request in challenger sales?

A powerful request is what a challenger seller makes of a prospect to determine if the prospect is serious about moving a deal forward. This might take the form of asking for internal data or access to key stakeholders and decision-makers. A prospect who is serious about moving the deal forward will get the sales rep what they need to work with others to make it happen.

What are the attributes of an effective challenger sales rep?

Challenger sales reps treat each prospective customer and deal as unique opportunities. They use industry knowledge and trends to share solutions and establish expertise as a consultant or trusted advisor. They deliver insights that challenge prospects to think about new and innovative solutions to business challenges and show how their product or service will deliver them.

Key Takeaways

As we’ve seen, developing true commercial insights is a big challenge for many complex sales organizations. Still, when sales reps are properly trained and equipped with them, anyone can be a challenger seller.

If your organization is working to implement the challenger sales method and messaging into sales collateral and proposals, look to Qwilr for support. Qwilr’s interactive sales materials can be used to teach, tailor and take control of each deal in your pipeline. Want to see it in action? Book a demo now.

About the author

Marissa Taffer, Founder & President of M. Taffer Consulting

Marissa Taffer|Founder & President of M. Taffer Consulting

Marissa Taffer is the Founder & President of M. Taffer Consulting. She brings over 15 years of sales and marketing experience across various industries to a broad range of clients.