What is the Challenger Sales Model? + 25 Discovery Questions

The Challenger sales model isn’t for the faint-hearted - but it brings rewards for sales organizations that can justify the effort. A study of 6,000 sales reps found that 40% of the top sales performers used challenger-style questioning as their primary sales approach.

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.

Each stage of the Challenger framework is mapped out for you, with a set of sample questions that will help you carefully prise apart your prospect’s pain points and assumptions. Using these questions, you’ll be able to establish a fresh understanding and help your prospects reach a new awareness of their processes, needs, industry, and how you’re positioned to help them.

During economic downturns why do some sales reps still crush 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:

What is the Challenger sales model?

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 customers 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, it's 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.

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 benefits of using the Challenger methodology?

• Improved customer engagement: Because the focus of the Challenger sales methodology is pointing out a problem customers likely didn’t realize they had, you gain their full attention. There’s an element of surprise, and when you solve the problem, delight. Customers on their toes, challenged, are much more engaged.
• Reduced sales cycles: The Challenger doesn’t beat around the bush. They truly challenge the client, which is a direct form of communication that gets right to the heart of the matter. This can dramatically shorten the sales cycle.
• Unique perspective: When you train sales reps to take the Challenger approach, you give them the opportunity to offer customers a unique perspective on a product or service. This engages sales reps as much as customers.
• Adaptability: The Challenger sales methodology, clear, direct, and slightly demanding, can be adapted to any industry. From data storage companies to retail suppliers, if there are sales involved, you can use the Challenger. It can even be applied to marketing!
• Improved cross-selling opportunities: There’s a level of relationship-building involved in the Challenger. For a client to move forward with this direct approach and accept the solution provided by the Challenger, there has to be trust. Once that trust is established, and the Challenger follows through, the opportunity for cross-sales through return and repeat business opens up.
• Increased revenue: Of course, with all of these benefits come increased revenues. Customers who trust you to provide solutions to problems they didn’t even realize they had and shorten the sales cycle are more likely to buy from you and refer others to you as well.

Is the challenger model right for your team and business?

While the challenger can be adapted to virtually any industry, there are a few specific businesses that are particularly served by employing this methodology.

• B2B sales: Businesses working with other businesses are much more amenable to a direct approach. If you’re in B2B sales, it is crucial to adopt the Challenger methodology and get all of your salespeople trained. They’ll be more likely to identify their client’s needs and explain how they can solve their problems.
• Innovative/disruptive products: Again, if you’re working with innovative or disruptive products, like new technologies, you want to come in hitting hard. The best approach with a disruptor is to identify the gap it fills. Then, explain why this product is the best fit for that gap.
• Highly competitive markets: Finally, when you’re trying to beat the competition, you don’t want to beat around the bush. You want to be the savior, the one who comes in with full knowledge of your client and presents the product that will help them make the progress they want to make.

Pros and cons of the challenger sales methodology and model

How to coach your sales reps to be challengers

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.

Coaching a hard worker

The issue with the hard worker is that they tend to be more “doers” than listeners. You can tailor their natural tendency to drive hard and move forward by encouraging them to be active listeners to uncover customers' needs. Draw on their desire to work hard by teaching them to do deep research on the customer’s business so they can offer impactful value.

Coaching a lone wolf

The lone wolf tends to disregard standard operating procedures, so help them see that the Challenger is the ultimate rebel, pushing to find hidden needs. Encourage the lone wolf to develop a unique insight into the customer’s business so they can challenge the customer’s assumptions and perspectives.

Coaching a relationship builder

The relationship builder is one of the easier roles to develop into a Challenger. They already know everything about the customer. Now, you have to teach them to challenge the customer’s assumptions about their problems and provide the solution. Encourage them to use data-driven arguments to add further value to the relationship they’ve already built.

Coaching a problem-solver

The problem solver is generally a people pleaser, more passive, waiting to be asked for help. Your job while coaching them is to teach them to build on their ability to solve problems but get right to the point, be assertive about presenting the problem and the solution — your product. Teach them to guide conversations in the direction of strategic value.

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:

• Are 3X more effective in complex sales
• 60% of salespeople earning $250K+ use Challenger sales methodology
• Over 50% of Fortune 100 companies partner with Challenger to improve their sales, marketing, and customer service performance

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 the challenger model 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.

Questions to ask when using the challenger sales framework

When conducting a sales conversation using the Challenger sales methodology, the seller will ask questions to lead the prospect through a six-stage process. The stages are:

• The Warm-up
• The Reframe
• Rational Drowning
• Emotional Impact
• Value Proposition
• Solution

Remember, it’s not a checklist. These key elements are intended to represent the changing dynamic of the communication between seller and buyer. We’ve provided you with lots of questions for each stage, but they’re intended to help you be the guide in the conversation—the questions themselves are not the guide.

It’s also important to be mindful of your prospect’s time—asking more than 15 questions at a time can bore or frustrate them.

The Warm-up

Like any sales conversation, challenger types need to create a positive atmosphere, establishing trust and rapport with the other person. In fact, this is especially important when you’re intending to create constructive tension later in the conversation.

These questions aim to engage on both a personal and professional level. They’re still relevant to the sale but also an opportunity to put the prospective customer at ease and establish mutual understanding.

1. “Can you walk me through your current process, from first step to completion?”

Here, you can demonstrate empathy and a genuine desire to understand the customer's business by showing interest in the prospect's processes. Asking them to describe ‘from start to finish’ helps them frame their response and encourages them to share a greater level of insight into their operational workflows and goals.

2. “How do you currently manage this particular problem on your team?”

If the customer has shared an issue or a pain point, this question provides you with more of an idea about how you could tailor a specific solution. It also demonstrates your interest in understanding the prospect’s unique situation and finding ways to add value.

3.“How much do you spend on your current solution? What results are you seeing?”

Being the first to raise the topic of money is important. It shows your interest in helping the prospect make informed decisions about their investments, positioning you as a partner who’s committed to helping them succeed.

It also shifts the conversation towards your solution's value proposition, which will prime the prospect to see the potential benefits later in the conversation.

The reframe

The reframe sets the challenger methodology apart from almost every other sales approach.

Unlike traditional sales approaches that aim to align with the customer's existing perspective, the reframe questions are designed to challenge the customer's thinking. They introduce new insights or perspectives that prompt buyers to reconsider their assumptions or beliefs.

These questions are strategically designed to introduce a provocative or disruptive idea, concept, or insight into the conversation.

Reframe questions often begin with phrases like "Have you considered that..." or "Did you know that..." followed by a statement or insight that challenges the customer's status quo.

Reframe questions are effective because they shift the customer's perspective and stimulate critical thinking.

They also change the buyer’s perception of the salesperson, helping dispel underlying negative connotations based on the idea of a shifty salesperson who only tells you what you want to hear. By showing that you’re unafraid to disagree, you send a message that telling the truth is more important to you than making the prospect like you. Executed correctly, this is a powerful way to build trust.

1. “Did you know that…?”

This question introduces a new perspective or insight that directly challenges the customer's knowledge or assumptions.

By framing the information as something surprising or unexpected, you’ll capture the customer's attention, encouraging them to reconsider their own perspective. This opens the door for a discussion about the potential implications of this new perspective for their own business.

2. “Have you ever considered…?”

This is effectively a more prescriptive version of the previous question, where the seller suggests a specific course of action.

If you frame the question as an invitation to contemplate an alternative approach, you’re inviting the customer to think critically and creatively about their challenges or opportunities.

This creates a sense of openness to new ideas and solutions, hopefully prompting further discussion about how your product or service can address their needs as you’ve reframed them.

3. “What would you do differently if you could/if you knew…?”

This question allows you to introduce the benefits of your solution, by framing it as a hypothetical change in circumstance within the buyer’s current situation.

If you ask them to think about how their actions would change with the benefit of your product, you open the door for a constructive dialogue about how you could support them to make changes that will help them reach this new status quo.

4. “What interests you the most about…?”

This question asks the prospect to identify which aspect of the reframed perspective resonates most with them.

Focusing on the customer's interests and preferences, you’ll demonstrate attentiveness and a willingness to customize your approach to meet the customer's needs.

It also provides valuable sales insights that enable you to tailor your pitch and positioning to highlight the most relevant aspects of the product.

Rational drowning

Perhaps the most commonly misunderstood stage of the Challenger sales framework is Rational Drowning.

Various explanations of this stage online describe rational drowning as a process where the seller uses data and statistics to back up the insights they’ve used to reframe the situation.

According to this interpretation, the seller ‘drowns’ the buyer in ‘rational’ explanation.

In actual fact, the ‘drowning’ in question results from allowing the prospect to experience the tension they might feel if they don't solve their current problem. While data may be used to back up insights suggested during the reframe, this stage should be considered as a deeper exploration of the cost of inaction - a darker flipside of the hypothetical situation suggested in the third reframe question above.

1. “Our customers see a 15% increase in ROI using our solution for this process. How much are you currently spending on this process?”

By linking the expected ROI to the prospect's current spending, you’ll demonstrate a clear understanding of their financial considerations (and emphasize the cost of not adopting your solution).

2. “Before finding our solution, one of our customers was struggling with this process. With our help they were able to solve the problem. Is this a priority for your team?”

This question lets you draw attention to additional aspects or implications of the insight you’ve provided that the customer might not yet have considered. It also provides social proof that your solution works in real-life contexts.

Highlighting the specific strategic goal achieved by your other customer and linking it to the prospect's broader objectives, you can emphasize the relevance and importance of addressing the operational area in question.

3. “Leading companies in your industry like (insert name) are switching to our solution. The #1 reason is (insert benefit). Is this benefit valuable to you?”

This question works by appealing to the prospect’s desire to stay ahead of the competition. By highlighting the specific benefit that drove their competitor’s decision to switch, you’ll reinforce the value proposition of your offering and position it as a competitive advantage for the customer.

The way the question is framed also makes it hard for the prospect to disagree.

Emotional Impact

Emotional impact questions are crucial in sales conversations.

They’re an essential tool to bridge the gap between rational evidence and personal connection. While rational evidence (such as data, case studies and industry statistics) provides logical reasons for considering a product or service, emotional impact questions allow reps to tap into the prospect's emotions, values, and aspirations.

1. “Is your organization committed to fixing the issue now?”

This question subtly taps into any underlying sense of urgency, addressing the prospect’s commitment to the organization.

By highlighting the need for immediate action, it prompts the buyer to reflect on their dedication to addressing the issue at hand, evoking emotions such as determination, responsibility, and accountability.

2. “What happens if you do nothing?”

This question forces the buyer to confront the consequences of inaction, addressing fully the issues raised during the Rational Drowning.

When you ask them to imagine the potential negative outcomes and impacts of not addressing the issue, you’ll evoke emotions such as fear, anxiety, and concern, increasing the urge to take action to avoid undesirable consequences.

3. “Who else is affected by this issue?”

Broadening the perspective, you invite the prospect to consider the ripple effects of the issue on others.

This question reminds the buyer of their duty to other stakeholders who may be impacted, such as employees, customers, or partners. By evoking emotions like empathy, compassion, and responsibility, you’ll motivate the customer to resolve the issue for the greater good.

Value Proposition

Through the previous four stages, you’ve hopefully helped your buyer reach a brand new understanding of an issue they weren’t aware of before.

You’ve worked with them to map out exactly how this affects their business, and the consequences for all involved should they choose to ignore it.

If this has been achieved successfully, the prospect will be keen to hear how they can solve this problem immediately.

Enter the Value Proposition. Any experienced salesperson will know exactly what’s required here - these questions aim to align the features and capabilities of the product or service with the specific needs and objectives of the customer.

By surfacing the value proposition, you’ll be laying the foundations that’ll help the prospect understand how the proposed solution can address their challenges, meet their requirements, and ultimately deliver value.

1. “How much time/money/resources/wasted opportunity is it costing you to continue with your current process?”

This question asks the prospect to quantify the impact of their current process on key resources such as time, money, or opportunities.

As you explore the tangible costs of inaction, you underscore the need for change and position your solution as a way to reduce costs and maximize efficiency.

2. “How are inefficiencies in this area preventing you from reaching your goals?”

This question encourages the buyer to connect the identified challenges with wider strategic initiatives or objectives within their organization.

Illustrating the direct impact of these challenges on strategic goals allows you to drive home the urgency of finding a solution. This will also position you as a strategic enabler that can drive alignment and success.

3. “Tell me about a decision you had to make to mitigate the current issues in this area?”

By acknowledging previous efforts to solve the issue, this question can help you position yourself as an ally and partner in the challenge.

The answer they provide can also help you tailor your value proposition and demonstrate how your solution provides a more effective and sustainable alternative.

4. “Help me understand what happens if we don’t address this issue now?”

Harnessing the urgency and anxiety that previous questions have already fostered, this well-phrased question allows the buyer to take ownership of the negative inaction scenario, motivating them to prioritize the issue.

5. “How does solving this issue bring you closer to your strategic objectives?”

This question is a more positively framed variation on the second Value Proposition question above. It reinforces the relevance and importance of your offering, encouraging the buyer to take action to realize their strategic vision.

Solution

Solution questions are designed to introduce your solution in a way that generates interest and encourages the prospect to take action. Framing the introduction of the solution as an "interest" Call to Action (CTA) invites the buyer to explore the product further, engaging in a deeper conversation about how it can meet their requirements and deliver value.

1. “Interested in finding out how we can help with this issue?”

This question encourages the prospect to explore the solution further and consider how it can address their specific pain points. Through expressing interest in understanding their challenges and offering assistance, it allows you to demonstrate empathy and a genuine desire to help.

2. “Are you open to learning more about solutions involving products like ours?”

When you create a discussion about solutions within a broader category, you’re asking them to consider the potential benefits of the solution. It also allows you to maintain a slightly more impartial advisory position, by talking about the category rather than your own specific product.

3. “Have you tried this type of solution before?”

This question follows on neatly from the wider category used in the previous question. Through acknowledging the prospect's past experiences and asking them to reflect on their previous experiences with similar solutions, you lay the groundwork for a more tailored discussion about how your solution differs (and why it may be a better fit).

4. “Would solving this issue help your team deliver on its strategy goals?”

This question returns to the themes explored in the fifth value proposition question, but with the potential to highlight more detailed benefits from your product or service. This question helps lead the prospect to consider the solution as a strategic investment that aligns with their organizational priorities.

5. “Are you game to explore how our company can help you with this?”

This emphasizes the salesperson's company as a trusted partner that can provide assistance with their challenges. Framed as a willingness to collaborate and support, the question creates an impression of your company as a valuable resource and prompts them to explore how its solutions can address their needs and deliver value.

6. “Does it make sense to explore how we can take this forward?”

As you round off your exploration of the solution with a push towards the logical next steps, this question encourages the buyer to engage further in the sales process and clears the way for closing the deal.

Read next: Sales closing questions

Challenger sales methodology template

When preparing sales proposals, particularly with the Challenger methodology, you want to be able to offer clean data and draw a clear pathway between problems and solutions. Because you need to be assertive and get right to the point, the best way to take this approach is with a template that will allow you to guide your client through the process.

The Qwilr template offers you the opportunity to do just that with by:

• Embedding your own content, like links, videos, surveys, Looms, and GIFs into every page
• Showcasing your value with an interactive ROI calculator
• Establishing your brand settings, including color, logo, fonts, and more
• Creating an asset library of reusable content for all of your sales reps to draw from
• Empowering your clients with interactive pricing plans and quotes so they can see what they’re getting from you vs. the competition

Follow the feeling, not the script

The challenger sales framework is designed for confident and experienced sales professionals - but with the right training and support, anyone can be a challenger seller.

It’s important to reiterate that these questions are suggestions designed to help you push and pull the sales conversation in the right direction at the right time. Although you’ll find combinations of these questions that work well together for your typical customer, it’s mainly about learning to guide the customer’s understanding carefully. You can’t really do that if you’re still glued to the script.

Immerse yourself in Challenger, and you’ll find that your instincts will start to take over, helping you lead your customers to their ideal solution and establish a fruitful partnership.

It’s also important to ensure that your sales collateral reflects the tone and direction of your sales process and sales conversations. Qwilr’s Challenger Sales proposal template is instantly customizable, helping you reinforce the unique insights and new perspectives you’ve used to inspire and persuade your new customer.