In-Depth User Interviews

I’ve seen a lot of enthusiastic designers and product folks jump into UX interviews with confidence just because they’re good at talking to people. The session feels relaxed, the user seems open, and everyone walks away feeling like they learned something real. The problem is that conversations are not data. Users try to be polite, helpful, agreeable, and socially “reasonable.” Without proper training, a UX interview collects stories that sound insightful but have nothing to do with real behavior. You end up designing for what users said politely, not what they actually do. What makes this funny is that in psychology, interviews are treated as one of the most complex research methods. Students spend semesters learning how to interview. They get observed, corrected, and even graded on how they phrase questions, how they hold their face, and whether they accidentally lead participants. Interviewing is a professional skill you learn and practice, not something you do because you’re friendly or curious. The best interviews don’t feel like conversations at all. The interviewer steps back and lets participants think slowly, sometimes awkwardly. A quiet researcher who listens, waits, and asks “What happened next?” learns a lot more than someone who jumps in to be helpful. Silence reveals truth. Polite conversation reveals performance. A semi-structured guide helps a lot. It keeps things focused without forcing yes/no answers. And asking about specific events beats asking for opinions every time. “Tell me about the last time you dealt with a notification” gives you real behavior. “Do you like notifications?” just gives you nice words. Rigor in UX doesn’t have to slow anything down. It just requires discipline. Document the guide. Write down your assumptions. Pair interviews with observation so you can see if words match actions. These little habits protect the findings from your own influence. And please, the “five users is enough” idea only applies to fictional usability testing, it does not work for uncovering real motivations, values, or decision patterns. You stop interviewing when people stop teaching you something new, not when you hit a magic number. In the end, UX interviews look simple, and that’s why they’re tricky. Anyone can ask questions. Very few people can stay neutral enough to uncover the truth behind the answer. When we treat interviews as investigations rather than conversations, our products get better, users get treated more accurately, and teams stop guessing. That’s the whole point of research: not to gather quotes but to uncover reality.

Ever spent months building a product, only to realize no one’s willing to pay for it? I’ve seen this happen more times than I’d like to admit—especially with first-time tech founders. One big reason? They didn’t talk to enough customers/users before building their solution. In some cases, they didn’t talk to anyone at all! Trust me, skipping these interviews is like flying blind—it rarely ends well. Building something people actually want starts here. Here’s what I’ve learned about doing user interviews effectively:   𝗧𝗶𝗽𝘀 𝗳𝗼𝗿 𝗨𝘀𝗲𝗿 𝗜𝗻𝘁𝗲𝗿𝘃𝗶𝗲𝘄𝘀 Focus on understanding, not pitching. Speak less. Listen more. Respect their time—15-20 minutes is enough. Ask open-ended questions to dig deeper. Find out if it’s a real pain point, not just a "nice-to-have." 𝗨𝘀𝗲𝗿 𝗜𝗻𝘁𝗲𝗿𝘃𝗶𝗲𝘄 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀 𝘁𝗼 𝗔𝘀𝗸 What’s the hardest part of this problem? When did it last happen? What caused it? How did you try solving it? Did it work? Why was it so difficult to address? What don’t you love about existing solutions? 𝗨𝘀𝗲𝗿 𝗜𝗻𝘁𝗲𝗿𝘃𝗶𝗲𝘄 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀 𝗡𝗼𝘁 𝘁𝗼 𝗔𝘀𝗸 "Would you buy this if I built it?" (It’s hypothetical and leads to false positives.) "Do you think this is a good idea?" (People want to be polite and will often say yes.) "Would you pay X amount for this?" (Pricing feedback without context isn’t reliable.) The goal is to uncover the truth, not get the answers you want to hear! #startups #startupindia #incubator #management #founder #uservalidation

In the first company we founded (and exited), we talked to thousands of users. Here at Pivot (YC S22), we just crossed our first 100. We are obsessed about speaking to users. But how do we talk to users effectively? Here are the top 4 tactics that have helped us gain valuable insights: 1/ Spend the first 5 minutes just talking about their lives. Don’t approach user conversations like a sales pitch. I know that it’s tempting to push the call towards your goals, or perhaps you are worried about wasting the other person’s time. But resist that urge! Instead, focus on genuinely getting to know them as if you’re making a new friend. First, this provides valuable context about who they are and what matters to them, helping you better make sense of their insights. Second, this deeper connection fosters genuine care for each user, which is key to building a successful company. 2/ Look for Lightbulb Moments. These rare moments provide unique insights that bring us closer to achieving Product Market Fit. For instance, Brian Chesky went down to Airbnb hosts just to realise that they needed help with photography, and Brian Armstrong phoned up all early Coinbase users just to learn from one guy the importance of a "Buy Bitcoin" button. By staying patient and attentive, a single comment from a user can spark a breakthrough idea. Even if 100 conversations don't yield Lightbulb Moments, the next one just might. It is our job to look out for them. 3/ “Huh! That’s interesting. Tell me more.” This is the go-to statement whenever a user shares something unexpected or unusual. Ask it, then pause and let them respond. While it may catch users off guard initially, it prompts them to reflect on their feelings, often resulting in a more detailed and nuanced explanation. This could just lead to a valuable Lightbulb Moment (as mentioned earlier). 4/ 5 consecutive “whys” when seeking an explanation. The 1st “why” might uncover something interesting, but it’s not until you get to the 5th “why” that you start to unearth their deepest motivations and underlying pain points. These are often things that the user themselves may not even be aware of. This technique helps us move past surface-level feedback to gain deeper insights, guiding our product development and UX from first principles. Ultimately, this helps us create something users truly want. The best founders continue to talk directly to their users even after they've reached $100M+ in ARR. It's crucial that we start making this our superpower today. I’d love to learn about other tactics that have worked for you as well, feel free to drop them in the comments below 👇

The first time I ran a user interview, I nearly threw up…but now I’ve led hundreds and I built a script that makes it 10x easier…… I still remember the first time I was asked to lead one. → My stomach dropped. → Anxiety kicked in. → And I had no idea what I was doing. I said yes anyway. Luckily, I’d watched a few senior designers do it before, so I had a general idea of what not to do. Since then, I’ve run hundreds of interviews, and picked up a few tricks that make the whole thing feel way less intimidating. Here are 10 things that helped me get better (and still help to this day): ✅ Prep like it’s a meeting with your boss. Know who you’re talking to, what your goals are, and double check your tech setup and prototypes. ✅ Use a loose script. Having a flexible guide keeps you on track and helps settle nerves. ✅ Don’t read it word-for-word. It’s not a telemarketing call. Use the script as a guide, not like a teleprompter. ✅ Follow the flow of the conversation. Circle back later. Tangents are often where the gold is. Let the conversation breathe. ✅ Tag-team when possible. Alternate with a teammate to reset between sessions, especially helpful for introverts. ✅ Listen more. Talk Less. Embrace the silence. The most insightful comments often come after a pause. ✅ Be relatable. Find common ground. Help them feel like they’re talking to a real human. ✅ Smile. Laugh. Loosen up. This isn’t a courtroom deposition or an interrogation Keep it friendly. ✅ Make them the smart one. I love to poke fun at myself, it lowers walls and opens people up. ✅ Say thank you, often. Show appreciation as you go. It builds trust and keeps the momentum going. User interviews aren’t just a research tool. They’re a business driver. Better insight = better product decisions = better outcomes. Want the exact script I use? 👉🏻 Drop a “Script” in the comments and I’ll DM it to you.

I've run hundreds of user interviews: at Amazon Capital One my own startup and as a Head of Marketing Here's the simplest sign one is going well: 90% — Stories about the user’s last time they struggled with the problem 10% — You're asking "Tell me more", “What do you mean by this?” and "What happened next?" 0% — You're pitching your idea The moment you start explaining your solution, you stop learning. If your ratio looks different, you're running a sales call disguised as research. You'll walk away confident and with completely wrong decisions.