Conducting User Experience Interviews

"Talk to customers" is classic startup advice. But not enough folks teach you how to talk to users in a way that gets you actual insights. Since launching Decagon and raising $100M over 3 rounds, we’ve learned a lot, especially about GTM. Here's how we've adapted our customer conversations to go beyond surface-level excitement and uncover real signals of value. We benchmark around dollars when discussing product features. Why? Because it’s easy to run a customer interview where the customer seems thrilled about a new idea we have. But excitement alone doesn’t tell you if a piece of feedback is truly valuable. The only way to find out is to ask the hard questions: → Is this something your team would invest in right now? → How much would you pay for it? → What’s the ROI you’d expect? Questions like these don’t allow for generic answers—they'll give you real clarity into a customer's willingness to pay. For example: say you float a product idea past a potential user. They're stoked by it. Then you ask how much they'd pay for said product—and the answer is $50 per person for a 3-person team. Is that worth building? It might be, depending on the outcome you're shooting for. But if your goal is to build an enterprise-grade product, that buying intent (or lack thereof) isn't going to cut it. If you'd stopped the interview at the surface-level excitement, you might have sent yourself on a journey building a product that isn't viable. By assessing true willingness to pay you can prioritize building what users find valuable versus what might sound good in theory. Get to the dollars as quickly as you can. It’s an approach that has helped us align our roadmap with what customers truly need and ensure we’re building a product that has a measurable impact.

Last week, I coached a product team through a user interview debrief. They were excited! Users had shown enthusiasm for a new feature! 🎉 But when I asked, “What problem does this solve for them?” the room went quiet. 🫣 This happens more often than we’d like to admit. 🧠 The Trap: Mistaking Enthusiasm for Validation When users say, “That sounds great!” we often interpret it as validation. But here's the catch: - Users want to be polite. - They might not fully understand their own needs. - As product teams, we may hear what we want. This is why relying solely on user enthusiasm can lead us astray. 🔍 The Solution: Semi-Structured Interviews We need to dig deeper to understand our users truly. Semi-structured interviews strike the right balance between guidance and flexibility. Key practices include: - Start with hypotheses: Identify what you believe to be true. - Ask open-ended questions: Encourage users to share experiences, not just opinions. - Listen actively: Pay attention to what’s said—and what’s not. - Probe for underlying needs: Seek to understand the 'why' behind their behaviours. This approach helps uncover genuine insights, leading to solutions that truly resonate. 🌟 Imagine the Impact By adopting this method: - Teams build products that solve real problems. - User satisfaction increases. - Resources are invested wisely, reducing wasted effort. It's not just about building features—it's about delivering value. 🦾 Take Action Next time you're planning user interviews: - Prepare a set of hypotheses. - Design questions that explore user experiences. - Remain open to unexpected insights. Remember, the goal is to understand your users, not just confirm your assumptions deeply.

𝟵𝟬% 𝗼𝗳 𝘂𝘀𝗲𝗿 𝗶𝗻𝘁𝗲𝗿𝘃𝗶𝗲𝘄𝘀 𝗳𝗮𝗶𝗹 𝗯𝗲𝗳𝗼𝗿𝗲 𝘁𝗵𝗲𝘆 𝗲𝘃𝗲𝗻 𝗯𝗲𝗴𝗶𝗻. 🧠 Why? Because most PMs ask surface-level questions and stop at obvious answers. Great user interviews don’t just ask questions. They uncover motivations, break assumptions, and reveal the “why” behind the “what.” 𝗔𝗳𝘁𝗲𝗿 𝗿𝘂𝗻𝗻𝗶𝗻𝗴 𝟮𝟬𝟬+ 𝗶𝗻𝘁𝗲𝗿𝘃𝗶𝗲𝘄𝘀, 𝗵𝗲𝗿𝗲’𝘀 𝘄𝗵𝗮𝘁 𝗜’𝘃𝗲 𝗹𝗲𝗮𝗿𝗻𝗲𝗱: 🔹Asking the right question is 10% of the job. 🔹Knowing how and when to ask it, that’s what leads to real insight. 🔹And insight is what separates good product decisions from guesswork. 𝗜’𝘃𝗲 𝗱𝗶𝘀𝘁𝗶𝗹𝗹𝗲𝗱 𝗲𝘃𝗲𝗿𝘆𝘁𝗵𝗶𝗻𝗴 𝗶𝗻𝘁𝗼 𝗮 𝗨𝘀𝗲𝗿 𝗜𝗻𝘁𝗲𝗿𝘃𝗶𝗲𝘄 𝗣𝗹𝗮𝘆𝗯𝗼𝗼𝗸 𝗳𝗼𝗿 𝗣𝗠𝘀 𝘁𝗵𝗮𝘁 𝗰𝗼𝘃𝗲𝗿𝘀: ✔️ Proven question structures ✔️ Conversation flow frameworks ✔️ Bias traps to avoid ✔️ Templates, tools, and real examples This isn’t theory, It’s what I use in real product discovery. 📥 𝗪𝗮𝗻𝘁 𝗮𝗰𝗰𝗲𝘀𝘀? Comment “𝗨𝘀𝗲𝗿” and I’ll share it with you. This guide is for PMs who want to move from taking feedback to shaping strategy.

Your Product Managers are talking to customers. So why isn’t your product getting better? A few years ago, I was on a team where our boss had a rule: 🗣️ “Everyone must talk to at least one customer each week.” So we did. Calls were scheduled. Conversations happened. Boxes were checked. But nothing changed. No real insights. No real impact. Because talking to customers isn’t the goal. Learning the right things is. When discovery lacks purpose, it leads to wasted effort, misaligned strategy, and poor business decisions: ❌ Features get built that no one actually needs. ❌ Roadmaps get shaped by the loudest voices, not the right customers. ❌ Teams collect insights… but fail to act on them. How Do You Fix It? ✅ Talk to the Right People Not every customer insight is useful. Prioritize: -> Decision-makers AND end-users – You need both perspectives. -> Customers who represent your core market – Not just the loudest complainers. -> Direct conversations – Avoid proxy insights that create blind spots. 👉 Actionable Step: Before each interview, ask: “Is this customer representative of the next 100 we want to win?” If not, rethink who you’re talking to. ✅ Ask the Right Questions A great question challenges assumptions. A bad one reinforces them. -> Stop asking: “Would you use this?” -> Start asking: “How do you solve this today?” -> Show AI prototypes and iterate in real-time – Faster than long discovery cycles. -> If shipping something is faster than researching it—just build it. 👉 Actionable Step: Replace one of your upcoming interview questions with: “What workarounds have you created to solve this problem?” This reveals real pain points. ✅ Don’t Let Insights Die in a Doc Discovery isn’t about collecting insights. It’s about acting on them. -> Validate across multiple customers before making decisions. -> Share findings with your team—don’t keep them locked in Notion. -> Close the loop—show customers how their feedback shaped the product. 👉 Actionable Step: Every two weeks, review customer insights with your team to decipher key patterns and identify what changes should be applied. If there’s no clear action, you’re just collecting data—not driving change. Final Thought Great discovery doesn’t just inform product decisions—it shapes business strategy. Done right, it helps teams build what matters, align with real customer needs, and drive meaningful outcomes. 👉 Be honest—are your customer conversations actually making a difference? If not, what’s missing? -- 👋 I'm Ron Yang, a product leader and advisor. Follow me for insights on product leadership + strategy.

Most product decisions are made long before a metric moves. They are shaped in conversations with users, moments of confusion we observe, things people hesitate to say out loud, and patterns that do not neatly fit into dashboards. Qualitative research today is not limited to interviews followed by a few highlighted quotes. There are rigorous, well-established approaches that make interpretation transparent, repeatable, and defensible. Methods like Framework Analysis help teams organize complex interview data in a way that allows real comparison across users and segments. Reflexive Thematic Analysis goes deeper, showing how meaning, emotion, and framing are actively constructed rather than passively extracted. When products behave differently across users, or when success and failure coexist in the same launch, methods like Qualitative Comparative Analysis explain why. Instead of asking what works on average, they reveal which combinations of conditions actually lead to outcomes. When teams need to understand causality rather than correlation, Process Tracing and Realist Evaluation map the mechanisms that connect design decisions to user behavior. Other methods prioritize depth and context. Interpretative Phenomenological Analysis preserves lived experience without flattening it. Video Reflexive Ethnography exposes invisible routines and expert behavior. Multimodal Discourse Analysis treats interfaces as systems of meaning, not just screens. Digital ethnography captures how culture forms and evolves online. Computational Grounded Theory allows qualitative insight to scale while keeping humans firmly in the loop. Qualitative UX is not about intuition versus data. It is about disciplined interpretation. When used thoughtfully, it becomes one of the most powerful tools we have for understanding why products succeed, fail, or surprise us. I wrote a detailed blog that dives into a practical framework for rigorous qualitative UX and market research. You can read more at PUX Lab: https://lnkd.in/gwBJS-UB

Your UX research is lying to you. And no, I'm not talking about small data inconsistencies. I've seen founders blow $100K+ on product features their users "desperately wanted" only to face 0% adoption. Most research methods are fundamentally flawed because humans are terrible at predicting their own behavior. Here's the TRUTH framework I've used to get accurate user insights: T - Test with money, not words • Never ask "would you use this?" • Instead: "Here's a pre-order link for $50" • Watch what they do, not what they say R - Real environment observations • Stop doing sterile lab tests • Start shadowing users in their natural habitat • Record their frustrations, not their feedback U - Unscripted conversations • Ditch your rigid question list • Let users go off on tangents • Their random rants reveal gold T - Track behavior logs • Implement analytics BEFORE research • Compare what users say vs. what they do • Look for patterns, not preferences H - Hidden pain mining • Users can't tell you their problems • But they'll show you through workarounds • Document their "hacks" - that's where innovation lives STOP: • Running bias-filled focus groups • Asking leading questions • Taking feedback at face value • Rushing to build based on opinions START: • Following the TRUTH framework • Measuring actions over words • Building only what users prove they need PS: Remember, Henry Ford said if he asked people what they wanted, they would have said "faster horses." Don't ask what they want. Watch what they do. Follow me, John Balboa. I swear I'm friendly and I won't detach your components.

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.

Customer interviews make or break products—but most of us are doing them completely wrong. Some obsess over customer problems. Others seek validation of their ideas. Which camp are you in? 👀 When you're pioneering a new space at the intersection of precision medicine and AI, there's no playbook to follow. You're writing the rules as you go. Early in our journey, I proudly showcased our multimodal data platform connecting clinical data, DNA, RNA, images and outcomes—only to face polite nods and zero urgency. Our sophisticated data integration wasn't what customers were actively seeking. In fact, many didn't even know they needed it. The breakthrough came when we stopped talking about our technology and started obsessing over their fundamental challenges. So what problems did drug developers actually face? They weren't looking for fancy technology—they were hoping to build disease models to identify patient subgroups that would respond to their therapies. But our true AHA moment started by asking this key question: "How are you solving this challenge today?" My latest blog post highlights a key mistake I’ve made and introduces a framework for radically improving your customer interviews: 1. Map Current Reality 2. Identify Friction Points 3. Quantify Value Gap 4. Test Specific Use Cases Our business transformed when I stopped talking and started listening—really listening—to the day-to-day challenges facing drug development teams. What we discovered fundamentally changed our approach... If you're pioneering something new in your industry, which customer discovery methods have worked for you? ♻️ Repost if this framework could be helpful to others. #PrecisionMedicine #CustomerDiscovery #ProductDevelopment #StartupLessons

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 👇

One of the fun parts of starting a new job is getting to ask “Why” a thousand times a day.* Why is this our strategy? Why is this our target customer? Why choose this problem? Why do we believe this market is big enough? Why do we believe our solution is differentiated? Lean Startup Canvas is a handy tool to remind ourselves of the kinds of questions to ask. If there are questions about revenue model, market size, or similar “what needs to be true for this to be big enough, and how confident are we that those assumptions can become true one day”, I like to model out all of those assumptions, and then see which we need to de-risk.* If there are questions about what customer we want to target, what Jobs To Be Done we want them to hire us for, what would make us a differentiated solution, I like to turn to generative research. This starts with recruiting 6-10 people who 1) have no prior relationship with me or anyone at the company, 2) are likely to represent the kind of customer we would focus on. Then, we should interview them with open ended questions that stay within the context of our focus area. And don’t sleep on the power of ethnographic research, diary studies, card sorting exercises, etc. Let them take us to where they want to go, what’s on their mind, what feelings do they have. What we’re hunting for are flare ups of emotion that can reveal a worthy pain point. These are subtle — an edge to their voice that lasts half a sentence, a big sigh or rolling of the eyes, a shaking of the head. We’re fully present during these interviews, because these moments are easy to miss. When we see those moments, we pounce. “Can you say more about that?” “How does that make you feel?” “How do you deal with that today?” These are the nuggets of gold that can lead us to a problem worthy of Product Market Fit, if we can validate that the problem is 1) wide spread enough, 2) solvable in a differentiated way, and 3) can be monetized sufficiently. What we absolutely must not do is pretend we’re doing generative research but actually we’re user testing solutions we already have in mind. Evaluative user testing is a great and under-utilized tool, but it’s not the same thing. If we go looking for proof that we are right, we’re pretty likely to find it because human brains are great at confirmation bias. Don’t: “What if I presented you with this solution, that could do x, y, z. Would you use it?” Do: “You mentioned [problem hypothesis]. Tell me about the last time [problem hypothesis] happened. What was it like? What did you do? How did it make you feel?” We’ll get to the solution design soon enough, but until we have confidence and clarity about what problem we want to solve, any solutions we do build are hard to evaluate.* —————— *If you’re interested in reading the footnotes as well as my work-in-progress thoughts (today: “good and cheap” > “great and expensive”), sign up for my free newsletter: https://lnkd.in/g44P3_rB