Getting real, honest insights from people is just about asking the right questions and listening carefully. Well……. It’s like trying to solve a Rubik’s Cube blindfolded while riding a unicycle… in the rain… with someone constantly telling you you’re doing it all wrong.
I just learned there’s an actual science to extracting insights that people don’t even realize they’re giving you. And in this article, I’m going to show you exactly how to master this critical skill in 5 practical steps that will completely transform your customer conversations, interviews, and market research.
The Painful Truth About Why Your Interviews Fail
Let me put on my imaginary glasses for this bit…
Most conversations, interviews, and feedback sessions are absolutely, completely, utterly useless.
Why? Because humans are delightfully terrible at telling you what they actually think, do, or need. It’s not that they’re lying to you (well, sometimes they are), but more often they’re lying to themselves without even realizing it.
See, when you ask someone “Would you use this product?” they’ll likely say yes because:
- They want to be nice
- They think they would use it (but won’t)
- They don’t want to hurt your feelings
- They’re imagining a fantasy version of your idea that’s 10x better than what you’re actually building
The thing is, opinions are like passwords – everyone has them, but most of them are rubbish. What you actually need are behaviors, facts, and concrete examples.
Hang on a second… the next bit is a doozy.
The Five Unbreakable Rules for Extracting Real Insights
1. Talk About Their Life, Not Your Idea
The first massive mistake everyone makes is pitching instead of listening. In February 2025, I watched a founder spend 15 minutes explaining his brilliant app concept, then ask “So what do you think?” The poor user just nodded and said, “Sounds great!”
Completely useless feedback.
Instead, structure your conversations around their existing behaviors and problems. Ask questions like:
- “Walk me through the last time you encountered this problem.”
- “What solutions have you already tried?”
- “How are you solving this currently?”
This approach comes from Rob Fitzpatrick’s “The Mom Test,” which is literally the bible for anyone serious about customer interviews. The core principle is brilliantly simple: if your mom would lie to you about your idea to protect your feelings, your questions are rubbish.
Now, let me put on my imaginary glasses again…
The word “feedback” means something completely different depending on who you ask. To a product manager, it might mean detailed insights about user behavior. To your best mate, it means saying “looks great!” so you’ll stop bothering them about your startup idea. To your mother, it means finding something—anything—positive to say while avoiding any criticism that might burst your entrepreneurial bubble.
Am I overthinking this? Definitely. But that’s part of the fun!
2. Master the “Five Whys” Technique
When someone gives you a surface-level answer, it rarely contains the insight gold you’re mining for. The “Five Whys” technique is insanely effective at getting beneath the initial response.
For example:
- “Why did you choose this solution?” (First why)
- “Why was saving time so important?” (Second why)
- “Why is efficiency such a priority for your team?” (Third why)
- “Why are quarterly targets structured that way?” (Fourth why)
- “Why does the company emphasize those metrics?” (Fifth why)
By the fifth why, you’re no longer talking about product features but uncovering fundamental organizational principles or personal motivations that drive decisions.
I tried this with a client in March 2025, and by the fourth “why,” they revealed their actual decision-making process, which had nothing to do with the features they initially claimed were important. Massive revelation that completely changed their product roadmap.
3. Embrace Strategic Silence
Let’s crack on with perhaps the most powerful tool in your arsenal: strategic silence.
Most people get massively uncomfortable with silence in conversation. They rush to fill it. But if you can master the art of asking a question and then shutting up completely, people will often fill that space with the most valuable insights.
It’s like trying to have a staring contest with a cat—awkward, uncomfortable, but extremely revealing when someone finally blinks.
In a January 2025 customer interview, I asked a participant what challenges they faced with their current solution, then deliberately said nothing for a full 15 seconds after their initial response. The additional information they volunteered during that uncomfortable silence completely changed our understanding of their needs.
What I’m going to do is suggest you count to eight in your head before responding to important answers. It feels like an eternity, but it works like magic.
Anyone else see where this is going? When people feel compelled to fill silence, they often reveal what they really think rather than what they think you want to hear.
4. Focus Obsessively on Past Behavior
Opinions about the future are fantasy fiction. Past behavior is documentary evidence.
Instead of “Would you use this?” ask “When was the last time you purchased something similar?” or “Walk me through how you solved this problem last week.”
The difference between these questions is absolutely staggering. One gets you a polite nod and worthless assurance, while the other reveals actual patterns of behavior that predict future actions.
In December 2024, I was working with a fintech startup that had received enthusiastic feedback about their investment tool from over 50 potential users. Sounds brilliant, right? But when they pivoted their questions to focus on past behaviors, they discovered that despite the enthusiasm, only 2 of the 50 had actually made similar investments in the past year. That’s the difference between useful and useless feedback.
Here’s the kicker… people will confidently predict their future behavior while having absolutely no idea what they’ll actually do when the moment arrives. I mean, seriously? I once confidently told a fitness app founder I’d definitely use their 5 AM workout tracker, while literally hitting snooze on my alarm for the third time that morning.
5. Look for Concrete Examples and Specifics
Vague feedback is about as useful as a chocolate teapot. When someone gives you general statements like “I would probably use this” or “This seems valuable,” push for specifics:
- “Can you give me a specific example of when you would use this?”
- “How exactly would you incorporate this into your existing workflow?”
- “What would you have to stop using to start using our solution?”
In November 2024, a SaaS company I advised completely scrapped a feature they’d spent months developing after discovering that while users said it was “interesting,” none of them could provide a concrete example of how they’d use it in practice.
Structuring Your Insight-Gathering Process
Now that you understand the principles, let’s assemble them into a proper interview framework that’s absolutely lethal for extracting honest insights:
1. The Warm-Up (5 minutes)
- Build rapport but don’t oversell it
- Explain the purpose: “I’m trying to learn, not pitch”
- Set expectations: “Negative feedback is incredibly valuable”
2. Current Behaviors and Context (15 minutes)
- “Walk me through how you currently handle this situation”
- “What tools or processes are you using now?”
- Apply the Five Whys to interesting responses
- Use strategic silence liberally
3. Pain Points and Challenges (15 minutes)
- “What’s the most frustrating part of your current approach?”
- “When was the last time you looked for a better solution?”
- “What’s stopped you from solving this already?”
- Push for specific examples and tangible impacts
4. Solution Exploration (10 minutes)
- Only now should you introduce your concept
- Focus on problems it solves, not features
- Watch for non-verbal cues and hesitation
- Apply the Mom Test rigorously
5. Commitment Probing (5 minutes)
- “What would have to be true for you to adopt this solution?”
- “Who else would need to be convinced?”
- “What budget/approval process would this go through?”
6. The Referral Request (5 minutes)
- “Who else should I speak with about this problem?”
- “Can you introduce me to someone who might have a different perspective?”
This structure works whether you’re validating a new product idea, improving an existing offering, or just trying to understand customer behavior better. It’s brilliant for product managers, founders, marketers, and even salespeople trying to understand prospect needs.
Hang on a second… let’s talk about a few modern tools that can make this process even more effective.
The Modern Toolkit for Insight Extraction
While the principles remain timeless, new tools have made capturing and analyzing insights significantly easier:
AI Recording and Transcription Tools
Tools like Vowel, Riverside, and Grain don’t just record your conversations; they provide AI-powered summaries, highlight key insights, and let you create clips of important moments.
I’m not saying to let AI replace human judgment—that would be a massive mistake. Rather, use these tools to ensure you don’t miss anything important while giving your full attention to the conversation.
Qualitative Analysis Software
For serious researchers conducting multiple interviews, tools like Dovetail and Delve help identify patterns across conversations that might not be obvious from individual interviews.
Mixed-Method Approaches
Combine qualitative interviews with quantitative data for the most comprehensive picture. If someone claims they “always” do something, check your analytics to see if that’s actually true. In April 2025, a client discovered their users were spending 3x longer on a feature they claimed was “just occasionally useful”—revealing a massive disconnect between stated preferences and actual behavior.
Common Pitfalls to Avoid (Like Your Life Depends On It)
The Pitching Trap
If you find yourself talking more than 30% of the time, you’re doing it wrong. Your job is to extract information, not explain your brilliant idea in excruciating detail.
Leading Questions
“Wouldn’t you agree this would save you time?” is not a question—it’s a thinly disguised statement seeking agreement. Instead, ask “How would this impact your workflow?” and let them volunteer time savings if it’s actually relevant.
Selection Bias
If you only talk to people predisposed to like your idea, you’ll get a skewed perspective. Actively seek out skeptics and people who might hate your concept—their feedback is pure gold.
Confirmation Bias
Be brutally honest about whether you’re interpreting responses to confirm what you already believe. In May 2025, I watched a founder completely ignore clear negative signals because they contradicted his vision—six months later, his product failed for exactly the reasons those interviews predicted.
Putting It All Together: From Insights to Action
Gathering insights is only half the battle. The next challenge is turning them into actionable decisions:
- Document patterns, not just individual responses
- Distinguish between needs, wants, and nice-to-haves
- Prioritize based on frequency and impact, not just the loudness of feedback
- Create hypothesis statements for testing: “We believe [user type] will [take action] because [insight from research]”
- Build small experiments to validate each hypothesis before committing resources
A cheeky little trick I’ve found massively effective is creating a “Skeptic’s Council” of 3-5 people who will ruthlessly question your interpretations and force you to prove your conclusions are valid.
The Bottom Line
Mastering honest insight extraction isn’t just about asking questions—it’s about creating conditions where people reveal what they actually think and do, rather than what they think you want to hear or what they wish were true about themselves.
The framework I’ve outlined here is based on proven behavioral science, not pop psychology or random opinion. It works insanely well if you apply it consistently and honestly.
If you want more of these insights and practical frameworks for understanding customer behavior, building better products, or growing your business, subscribe to my newsletter where I share weekly actionable advice.
What’s your experience with customer interviews? Have you found certain questions particularly revealing? Or have you made spectacular mistakes you can warn others about? I’d love to hear your perspectives in the comments!
Remember, the goal isn’t to hear what you want to hear—it’s to discover what you need to know, even when it’s not what you hoped for.
