5 Proven Questions to Reveal Customer Insights - Miss These, And You’re Leaving Money on The Table

Most companies think they know their customers, but here’s the problem: They don’t ask the right questions. They either stick to surface-level inquiries or focus too much on selling rather than understanding. As a result, they miss out on insights that could uncover million-dollar opportunities.

Why is this a problem? Without digging deeper, you’re left guessing what your customers really need. This leads to wasted resources on features nobody wants, marketing that doesn’t resonate, and even customer churn. Imagine the revenue left on the table simply because you didn’t ask the right questions.

Here’s the solution: during customer interviews, use strategic questions that reveal hidden pain points, ideal features, and purchasing criteria. These questions aren’t complicated, but they need to be asked in a way that encourages customers to open up and share their real experiences.

To get started, I’ll share the five golden questions I’ve used in 100+ interviews to uncover opportunities worth millions. Along the way, I’ll give you tips on how to use these insights to refine your product, marketing, and sales strategies.

1. What’s the biggest challenge you’re facing in your role right now?

This question brings the most pressing problem to the forefront - the one they wish they could solve immediately. Knowing this helps you understand where their priorities lie and positions your product as a direct solution.

Many people think they already know what their customers’ main problems are. They create marketing copy based on assumptions, which often miss the mark because they’re solving the wrong problem. This mistake leads to missed opportunities and wasted resources.

Instead, ask this question and listen carefully. If your product addresses their challenge, use their exact words in your marketing to resonate with them. If your product doesn’t directly help with their issue, explore adjacent solutions. For example, if they struggle with regulatory compliance in a complex industry, and you offer a data management SaaS, consider creating an integration with a compliance tracking tool to address their primary pain point.

For example: A customer says, “My biggest challenge is maintaining compliance with ever-changing regulations in our industry.”

Before, your messaging might have focused on “streamlining data management.” Now, you shift to, “Stay compliant with real-time regulation tracking integrated into your data management system.” This change speaks directly to their pain point, making your product the obvious solution.

The words they use to describe their challenge are your key to crafting messaging that resonates and exploring new product opportunities.

2. If you could change one thing about your current setup/our product/service, what would it be?

This question identifies the small yet significant frustrations that can greatly impact user experience. Knowing this helps you uncover quick wins that can dramatically improve customer satisfaction and loyalty.

Many companies assume these small issues don’t matter. They focus on big-picture features, thinking customers can overlook minor inconveniences. This approach can backfire, leading to frustration and eventual churn.

Instead, ask this question and pay close attention to the specifics of their feedback. Implementing small adjustments, like refining a workflow within your software, can significantly enhance their experience. If a B2B SaaS customer mentions that an analytics dashboard in your product is difficult to navigate, prioritise streamlining it to remove unnecessary friction.

For example: A customer says, “I wish I didn’t have to export data to Excel every time I need to generate a report.”

Before, you assumed customers could use workarounds. Now, you introduce an in-app reporting feature that automates the process. This small tweak improves their day-to-day workflow and builds trust.

Addressing these seemingly minor snags makes your product more user-friendly and proves to customers that you’re listening to their needs.

3. Can you walk me through your typical day? Where does our product fit into that?

This question provides insight into how your product integrates into their daily workflow. Understanding this helps you identify touch points where your product could add more value or integrate with other tools they use.

Many companies assume they know exactly how customers use their product. They map out ideal customer journeys without considering the actual context of use, leading to missed opportunities for deeper integration.

Instead, ask them to describe their day in detail. Listen for pain points, bottlenecks, or moments when they’re manually completing tasks that your product could automate. If you hear that your B2B SaaS product is only used at the end of the day to log information, explore ways to embed your solution into their daily routine for a more seamless experience.

For example: A customer says, “I use your software to generate compliance reports, but only at the end of the month because it takes too long to gather all the necessary data.”

Before, you assumed they were utilising your software continuously. Now, you introduce real-time data syncing, allowing them to access updated compliance statuses daily.

This simple change integrates your product more naturally into their workflow.

The more your product becomes part of their routine, the more indispensable it becomes, reducing the risk of churn.

4. When choosing a product or service like ours, what factors are most important to you?

This question reveals the key criteria they use when evaluating solutions. Understanding these factors helps you focus your marketing and sales efforts on what matters most to them.

Many businesses make the mistake of showcasing all their features, assuming customers will sort through them to find what they need. This approach dilutes your message and can overwhelm prospects, making your product appear complicated.

Instead, ask this question and adapt your messaging to align with their priorities. If they value data security and regulatory compliance, emphasise these aspects in your marketing. For instance, highlight how your B2B SaaS platform is SOC2 compliant and offers end-to-end encryption.

For example: A customer says, “We need a tool that integrates seamlessly with our existing ERP system.”

Before, your messaging might have focused on your product’s unique automation features. Now, you shift to, “Effortlessly integrate with leading ERP systems to streamline your operations.” This aligns with their decision-making criteria and makes your product more attractive.

Focusing on what they value most increases the chances of converting leads into customers.

5. If you could design a product that perfectly meets your needs, what would it look like?

This question exposes gaps in your current product and highlights potential areas for future improvement. It also reveals where you might be overcomplicating things.

Many companies believe they need to pack their product with features to cater to every possible need. However, customers often prefer simplicity and focus. By not asking, you risk overcomplicating your product and missing the mark on what truly matters.

Instead, ask them to describe their ideal solution. Listen for common themes, such as requests for simpler interfaces or additional integrations. Use this feedback to guide your product roadmap, focusing on enhancing areas that will provide the most impact.

For example: A customer says, “I wish the dashboard showed real-time data in a simplified format, without all the extra filters.”

Before, you kept adding more filters and customisation options, assuming this would add value. Now, you introduce a simplified dashboard view with key metrics displayed in real time. This change aligns with their vision of an ideal product and can drive higher user satisfaction and adoption.

TL;DR - To sum up the key takeaways…

What’s the biggest challenge you’re facing in your role right now? – Directly ask your customers what their top priority problem is. Use their exact words to tailor your product and marketing strategy.

If you could change one thing about your current setup/our product/service, what would it be? – Identify minor frustrations that can turn into quick wins. Fixing small snags boosts customer satisfaction.

Can you walk me through your typical day? Where does our product fit into that? – Learn how your product integrates into their daily workflow. Find opportunities to embed your product more deeply.

When choosing a product or service like ours, what factors are most important to you? – Discover their decision-making criteria. Focus your messaging on the key features they value most.

If you could design a product that perfectly meets your needs, what would it look like? – Understand what they envision in an ideal product. Use this insight to refine your product and avoid overcomplicating it.

You’re probably leaving money on the table by not asking the right questions. The reality is, many B2B companies operate on assumptions rather than real customer insight. You might think you know what your customers want, but until you hear it in their own words, you’re shooting in the dark.

Imagine tailoring your product, marketing, and sales strategies directly to their biggest pain points. How much faster could you drive adoption? How many more customers would be knocking on your door?

It’s time to stop guessing. Either implement these questions now or hire someone who knows how to dig deep and uncover the insights that lead to growth.

We help B2B companies in complex industries get actionable customer insights in just 4 weeks through a ‘done-for-you’ sprint. If you’re ready to discover what your customers really want, let’s talk. Just ask a question or book a call to get started.