User Interviews - Asking The Right Questions

Staring at the square tiles, thoughts pass as genius suddenly strikes you. Touched by destiny, you quickly pull up, push the button behind you, and eagerly surge back through the crowd. As you arrive between your group of trusted advisors, you passionately burst out your idea. And there it is, as their heads gradually start to nod and nurturing smiles stare back at you, you hear the words “I think that’s a great idea, honey.”. You already knew it; it’s genius! It’s time to get this product to market. Or maybe not..

We all have those moments when ideas hit us, and we grasp toward that sensation of glorious validation. Proud and confident, we tend to forget that the person in front of us might be more motivated to come across as positive and supportive — rather than telling harsh but insightful truths. They might even really believe in your idea, but does it truthfully solve a big enough problem to show up in a store and put down the sticker price? 

Asking the wrong questions, or asking questions the wrong way — more often than not will give you the wrong answers. It’s a slippery slope that will cost you time, money, and above all - opportunity.

Asking the right questions is both an art and a science — a game of psychology that requires skill and neutrality from the interviewer. Let’s explore how to ask the right questions and unlock genuine, actionable insights about your audience. Mastering this skill will enable you to turn polite conversations into power tools for building products and strategies that actually work.

Most people fall into the same traps: pitching their ideas too eagerly, asking leading questions, or looking for validation instead of truth. 

Asking the right questions isn’t just about gathering data — it’s about uncovering those truths. When designing a product or strategy, it’s tempting to seek validation for your ideas. But truth delivers more value than agreement, and likely leads you to completely different outcomes. Finding the uncomfortable answers allows you to validate your idea and more likely turn it into a valuable solution. This shift in mindset is critical for creating successful products and strategies.

If you push for unwarranted validation you risk wasted resources and products nobody wants. But the right questions? They unlock insights, validate real problems, and guide you to solutions people will actually use.

Biases are the inclinations or preconceived notions someone has about certain topics. Bias can be unconscious or deliberate, don’t just come from the person you’re interviewing — it also comes from you. As an interviewer, you may unconsciously:

• Seek Validation: Looking for answers that confirm your ideas.
• Ignore Signals: Overlooking feedback that doesn’t align with your assumptions.
• Push narratives: The instigator of contextual bias when you steer the conversation by asking only leading questions or emphasizing specific statements, which can inadvertently influence the participant’s responses.
• Make Premature Judgments: Forming conclusions about the interviewee’s feedback before fully understanding their perspective, may prevent a deeper exploration of important points.

To find truth and uncover actionable insights, you need to shift your approach. Here are the core principles to guide your interviews:

People are naturally motivated to pitch their ideas. Instead of learning about the user, it’s tempting to sell your solution and defend it against any criticism. After all, they probably just didn’t fully understand the idea right? This approach biases responses and shuts down honest feedback.

Your job isn’t to sell your idea — it’s to understand the person in front of you. The moment you pitch, the interviewee will start giving answers based on what they think you want to hear. If your question is misinterpreted, learn from the moment and let it play out.

Start every interview with curiosity, not assumptions. Be ready to pivot your thinking based on what you hear. Leave silent moments to allow the user to open up, dig into unexpected answers, and ask them what motivated them to make certain decisions.

Instead of saying, “Would you use this?” ask, “How do you currently handle [specific task]?” This shifts the focus to their experience and behaviors.

Asking Leading Questions is another common mistake. Questions like “Would you use this app?” almost guarantee a polite “Yes” or “I’ll probably try it out”, but they tell you nothing useful.

People are better at describing their current or past behaviors than predicting what they might do in the future. Instead of asking hypothetical questions, dive into their real-life experiences.

For example:

• Bad: “Would you use this budgeting app?”
• Good: “Can you walk me through how you manage your finances today?”

As humans, we naturally want to hear what aligns with our ideas. But this can blind us to critical feedback — or worse, make us ignore obvious red flags.

Your solution doesn’t matter unless the problem is real. Before building anything, validate that the problem exists and is significant. Ask questions like:

• “What’s the hardest part about [specific task]?”
• “Have you tried solving this problem before? If so, how?”

Emotional reactions during an interview — such as hesitation, enthusiasm, frustration, or even subtle changes in tone — are clear signals worth exploring. Emotional cues often highlight pain points or areas of opportunity that users might not articulate directly. By digging into these moments, you can uncover deeper, actionable insights.

When you notice an emotional reaction, gently probe further. For instance, you might say, 

• “You seemed frustrated when describing that process. Can you tell me more about what made it challenging?”

Validate Their Feelings: Acknowledge their emotions to build trust and encourage openness. The right questions can make participants feel understood.

• “That sounds frustrating” or “I can see why that’s exciting”

Always end your interview with an actionable next step. Ending your conversation with a clear ask helps to build momentum and extract real-world validation from the conversation. It also signals to the user that you are serious about the next steps and that their time was valuable.

Many people might say polite, non-committal things like, “This sounds great!” or “I’d love to use this!” during the interview. These statements don’t reflect actual interest or commitment. An actionable ask forces them to act, separating genuine interest from casual approval.

• Ask for referrals: “Do you know anyone else who might face similar challenges?”
• Ask for a commitment: “Would you be willing to try a prototype or share your feedback on it?”

Beyond the psychology of a good user interview, there are a few practical tricks that can further elevate the quality of your research.

Whether in-person or remote, ensure the setting is suitable and conducive to conversation.

Ensure the interview can be conducted without unwanted interruptions. Separate participants from people they know and ask them to turn off their phones.

Interviews are powerful, but pairing them with other tools like surveys or data analytics can provide a more complete picture. Use interviews for depth and analytics for breadth.

User interviews are a powerful tool for building products people actually want. Being able to ask the right questions is a tool in life, no matter the application. Start asking better questions, and watch as honest, actionable insights transform your ideas and understanding.

The next conversation you have with someone could be the one that changes everything.