I’m revisiting this topic because the question of how I would approach a new feature request recently stumped me. I fumbled with some explanation that made no sense. Maybe I am not as quick as I think I am. It got me thinking: have you ever watched a skilled craftsperson at work? I know this stream of thought is somewhat tangential to this topic but bear with me. Something is mesmerizing about the way their hands move with practiced precision, each gesture revealing an intimate understanding of their materials. This same level of artistry exists in thoughtful user interviews, where asking the right questions creates a canvas for genuine human insight.

I witnessed this truth recently while collaborating with an emerging spice subscription service. As we gathered around a wooden table with potential customers, I noticed how the conversation shifted when we abandoned our scripted questions about features and preferences. Instead, when we asked about specific moments—the frustration of discovering stale spices hidden in cabinet corners, the disappointment of bland flavors in a carefully prepared meal—their expressions changed. Eyes widened. Hands gestured more animatedly. Stories flowed.

These moments of authentic connection reveal something profound: most product development efforts fail not because we lack creativity or technical skill, but because we ask the wrong questions during crucial discovery phases.

Beyond Surface-Level Validation

Many founders unwittingly sabotage their user research by asking questions that only scratch the surface:

“Do you like our idea?” “Would you use this product?” “Is this a good solution?”

These questions may seem productive, but they ultimately yield little more than polite nods and superficial validation. They confirm what we already believe rather than challenging our assumptions or revealing unexpected truths.

The difference between mediocre products and transformative solutions often lies in this delicate interview dance—moving beyond what people say they want to understanding what they truly need.

5 Questions That Unlock Genuine Insight

The next time you sit down with potential users, try replacing your standard questionnaire with these five perspective-shifting questions:

1. “Take me through the last time you experienced [problem].”

Instead of asking about hypothetical situations, focus on specific memories. Notice the subtle shifts in posture as someone recalls struggling with stale spices or feeling overwhelmed by bulk purchasing. Listen for the sigh that accompanies the memory of wasted ingredients or the slight smile when describing an improvised solution.

When you anchor questions in authentic experiences, you uncover the rituals, habits, and emotions surrounding the problem—all essential ingredients for meaningful innovation.

2. “Tell me about a time when you had a terrible experience because of [problem].”

We learn more from moments of frustration than moments of satisfaction. When someone describes the disappointment of serving a special anniversary meal that lacked flavor due to old spices, you gain insight into both the practical challenges and emotional stakes.

Don’t rush this conversation. Follow each thread with gentle curiosity: “How did that make you feel?” “What happened next?” The richest insights often emerge in these thoughtful pauses.

3. “Have you ever come up with your own hack to solve [problem]?”

People are naturally inventive, creating workarounds for persistent problems. One woman described labeling her spice jars with purchase dates and setting calendar reminders—a clever system born from frustration that revealed her underlying need for freshness tracking.

These improvised solutions offer blueprints for features your users will actually value—because they’ve already invested time in creating them.

4. “Was there a time you felt over the moon because of a solution to [problem]?”

Joy is as instructive as pain. When someone’s eyes light up, describing the first time they cooked with freshly ground spices, you’ve discovered something worth amplifying in your solution.

These moments of delight become north stars for product development—experiences worth recreating and enhancing.

5. “If you had a magic wand that could make the perfect solution appear, what would it look like?”

This question frees people from current limitations and practical constraints. It invites them to dream alongside you, often revealing aspirations and values that more practical questions miss entirely.

One interview participant described a system that would automatically track the freshness of her spices and suggest recipes based on what needed to be used. This vision ultimately shaped our client’s digital integration strategy.

Building Solutions That Resonate

The subtle art of user interviews isn’t about collecting opinions—it’s about gathering stories rich with emotional truth. When you understand not just what people do but how they feel while doing it, you build products that resonate on a deeper level.

By focusing on specific experiences rather than abstract preferences, you’ll discover what truly matters to your users. These emotion-driven insights become the foundation for solutions that people not only use but also love.

Have you conducted user interviews for your product? Which questions yielded the most surprising insights? I’d love to hear your experiences in the comments below.