25 Challenger Sales Questions for Effective Discovery

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.

However, not every sales rep is prepared to purposefully cause tension and establish positions and perspectives deliberately at odds with their prospect’s worldview.

Even experienced sales professionals may be unsure how to create a framework that allows them to sell in this bold style. That’s why we’ve created a set of questions to get you started.

Here, 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.

What is challenger sales?

‘The Challenger Sale: Taking Control of the Customer Conversation’, published in 2011, was written by Gartner researchers Matthew Dixon and Brent Adamson. Upon its release, it changed the sales methodology landscape.

The book methodically explores their research and findings based on comprehensive interviews they conducted with thousands of sales professionals. They were able to categorize every salesperson they interviewed into one of five distinct sales personas. These were:

The Hard Worker: who strives to improve their position. Their answer to everything is to work harder.

The Lone Wolf: This is a confident high performer who doesn’t always follow the rules or play well with others.

The Relationship Builder: Relationship builders focus on connection.

The Problem Solver: By bringing customer service energy, they focus on being the providers of solutions.

The Challenger: with a deep understanding of the customer’s industry, issues, and motivations, the challenger aims to disrupt the status quo and force prospects to rethink their opinions and perspectives.

Dixon and Adamson found that over 50% of the highest-performing enterprise sales reps, even during a recession, were challenger types.

They also found that the skills needed for successful challenger selling weren’t innate—they could be taught. They devised their methodology and wrote a book explaining how to train each of the other personas, reorienting their skills to help them become challenger sellers.

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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.

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