Engage More Sales Prospects with GAP Questions

Here’s the reality: customers believe that the sales professional who truly understands their problem is the most qualified to solve it. 

So, how can you prove you’re the right person for the job? 

While your first instinct may be to jump straight into pitching your product, this approach often overlooks the full scope of the issue and alienates prospective clients. 

To truly showcase your expertise—and demonstrate that you’ve taken the time to understand their needs—you need to ask thoughtful, deep questions that spark meaningful conversations.

In Episode 105 of our SALES with ASLAN podcast, co-founder and CEO of ASLAN, Tom Stanfill, discusses a powerful questioning strategy called GAP (Get At the Problem) questions that do exactly this.

Mastering these thought-provoking questions can help position you as a trusted partner who truly understands their client’s challenges and, most importantly, creates a pathway to closing the deal.

The Purpose of Asking Thought-Provoking Questions

As a sales rep, asking good questions goes beyond just gathering information—it’s about uncovering your customer’s core challenges. Thoughtful, deep questions help prospects recognize issues they might not have realized, which, in turn, helps you tailor your solution to address their specific needs in a way the competition can’t.

Not all questions are created equal, though. Many standard go-to questions, while necessary in some instances, are insufficient, providing short responses that don’t glean additional insight to give you an edge. Avoid these common pitfalls that can leave your conversation dead in the water:  

• “What does your company do?” Questions you already know the answer to (or should know the answer to) can feel disingenuous and don’t foster deeper discussion.
• “What’s your budget?” On its surface, this question seems perfectly fine. Upon closer inspection, though, this question can be answered quickly without reflection and doesn’t have a natural follow-up, which can stall a conversation and leave you scrambling to fill the space.
• “How can I help you?” Not only are these types of questions overly vague, but they can make the conversation feel directionless, leading to missed opportunities.

With these in mind, it’s now easy to see what makes great thought-provoking questions. They’re clear, concise, and open-ended, encouraging meaningful dialogue (and deeper insights). Here’s what makes them effective:

• “Why are you looking to purchase now?” While simple, questions like this often require additional outside context and further follow-ups to fully answer. When people are used to giving surface-level responses, starting this type of dialogue can be crucial to get to the meat of the situation.
• “What about previously buying a similar service was disappointing?” Referencing past experiences helps you learn what’s worked (or not) for them before and avoid similar shortcomings.
• “What’s holding your team back?” Encouraging self-reflection helps the customer clarify their challenges for themselves. Aligning how you both perceive the situation gives you a stepping stone to further investigate how your solution addresses their needs.

What Are GAP Questions and Why Should Sales Professionals Use Them?

GAP questions stand for "Get At the Problem" questions and are a strategic, conversational approach to uncovering deeper insights. GAP questions are customer-centered, meaning they focus on uncovering the customer’s desired outcome and help them process what’s required to get to their goal. Once you have that information in your back pocket, it’s easy to demonstrate your expertise in helping them achieve it.

How do they do this, though? GAP questions are designed to be thought-provoking, often requiring potential customers to reflect instead of reflexively answering. Through a back-and-forth dialogue, these questions reveal unconscious business needs while allowing sales reps to highlight their value and expertise in their responses. 

For example, a sales rep might ask, “What’s the biggest challenge your team is facing right now?” This open-ended question can’t be answered with one or two words. In fact, it invites the prospect to provide additional context that could be crucial for this sale. From there, the rep can guide the conversation to explore how their solution aligns with the prospect’s goals.

By guiding the customer through the conversation with well-placed questions, you encourage them to evaluate the situation from a new perspective and, eventually, land on your solution themselves, creating an environment where the prospect is more likely to embrace your solution.  

The Formula for Asking Good, Deep Questions in Sales Meetings

Putting GAP questions into practice may seem daunting at first, but leading these conversations can become second nature when you know what areas to address.

To get the most out of your sales conversations, your questions should address the three Es: engagement, expertise, and embrace.

Mastering the three Es is key to overcoming common sales challenges while building stronger, more authentic, relationships with prospects.

Promote Engagement

In virtual selling, it’s easy for conversations to turn into one-sided monologues. Rather than taking the reins and doing all the talking, your questions should invite your prospects to share their thoughts and concerns, creating an environment where both of you can explore the issues more deeply. 

When planning your GAP questions, consider if they foster a two-way dialogue. This helps maintain customer engagement by sparking thoughtful reflections and encouraging them to stay actively involved. This ensures the conversation remains focused, valuable, and meaningful while keeping the prospect invested in the discussion.

Demonstrate Expertise 

Today, customers have access to an overwhelming amount of information online, making it more difficult for sales reps to stand out as trusted experts. Salespeople need to demonstrate their credibility in assisting their customers in the decision-making process. 

With this in mind, your GAP questions should be tailored to uncover the root causes of your prospects’ challenges—ones they might not even be fully aware of themselves. 

Once you know this, it’s easy to showcase your expertise by sharing previous successes, breaking down complex processes, or highlighting your unique value proposition to demonstrate the ways your product directly addresses their specific needs. This positions you as a trusted partner with their best interest in mind, rather than just another salesperson.

Embrace a Solution

Ultimately, your goal is to get the prospect to embrace your solution. But, this is less about convincing customers to buy and more about helping them make the best decision for their business. 

Effective GAP questions guide prospects to view their problems from a new perspective, helping them realize how your solution aligns with their needs. 

Tom Stanfill goes on to say, “People buy more when they’re talking than when you’re talking. People don’t argue with their own data.” And the numbers agree. One study found that the most successful B2B sales conversations happened when the prospect spoke at least 57% of the time on average. 

So, as sales professionals, we need to learn to listen more than we talk and guide our prospects into talking with extremely tailored questions. 

When sales reps guide the conversation with thoughtful questions, they not only keep the prospect engaged but also create an environment where the prospect discovers the solution on their own. When customers arrive at the solution themselves, they are far more likely to embrace the recommendation—because it feels like their idea. 

How to Use GAP Questions to Solve Core Selling Challenges

GAP questions are designed to reveal deeper insights through open, authentic conversation that surface-level questions can’t provide. Below are several ways to drill down into your prospects’ challenges to help you sharpen your pitch, position your solution more effectively, and avoid common pitfalls that might derail your sales.

Discover the Core Problem 

As sales reps, it’s easy to get fixated on your products and solutions, which, while valuable, can narrow your view and prevent you from seeing the broader picture. Without understanding how your solution fits into the larger ecosystem of your customer’s business, you’re at risk of offering a solution, not the solution. 

So, how do GAP questions help you uncover these macro issues within your prospect’s business? Communication expert Marcus Sheridan puts it well: "The answer you’re after is at least three questions deep." In other words, you need to dig beyond surface-level responses to uncover the underlying pain points.

By fostering thought-provoking conversations, GAP questions help you identify these true pain points—granting you insights that will enable you to position your solution in a way that resonates with your prospect’s unique situation.

Understand What It Takes to Solve It

Once you’ve uncovered the core problem, the next step is understanding what’s required to solve it—beyond just your product. Instead of jumping into your pitch, instead, ask yourself: What else is needed to address this challenge? What pieces of the puzzle are missing?

Then, use your deep questions to become a student of your client’s industry. Question what best practices or formulas are required to fully address their challenges, including any components beyond your own offering.

When you demonstrate a deep understanding of both the scope of the problem and the comprehensive solution, you position yourself as a trusted partner—someone who can guide them to success, not just sell them a product.

Identify Your Competitive Differentiation

Identifying your competitive differentiation is often something that happens before you even start putting GAP questions into practice. Knowing your unique value proposition helps you preemptively respond to questions that may arise during conversations and guide them toward the areas where your solution truly excels. 

These dialogues are a chance for potential customers to learn from the questions they ask, so use this opportunity to subtly educate them on commonly overlooked features and highlight your competitive advantages. 

Understanding your competitive edge allows you to clearly demonstrate how your solution is better suited to their needs than alternatives, showing that you’ve taken the time to understand not just their challenges but also what sets your offering apart.

Facilitate a Meaningful Dialogue

It may seem simple, but the key to successful sales conversations often lies in asking the right questions that lead to a two-way dialogue. This isn’t just about gathering information—it’s about creating an exchange that feels collaborative. By asking thought-provoking questions, you not only gain valuable insights into your customer’s challenges but make them feel seen, understood, and cared for. 

In return, your considered responses build trust and position yourself as a partner who is genuinely invested in their success and future, rather than just a salesperson looking for a quick win. This deeper connection not only improves your chances of closing a deal but also sets the stage for long-term relationships, where they turn to you first over your competitors.

Better Questions Beget Better Outcomes

GAP questions are an invaluable tool for sales professionals who want to stand out in today’s competitive market. This approach not only helps you better understand customer needs but also positions you as a trusted partner, guiding them toward a solution that aligns with their business goals.

With the right questions, you can engage prospects, showcase your expertise, and help them realize that your solution is the answer they’ve been seeking.

By integrating GAP questions into your sales strategy, you’ll be better equipped to navigate complex sales conversations, foster stronger relationships, and close deals more effectively. 

Contact us today to schedule a consultation and discover how to put these strategies into practice with your sales team.