How to Build Openness in User Interviews

I've always been a fan of user interviews. They're a great way to get insights into what users need and how they behave. But over time, I've come to realize that the traditional way of doing user interviews, with all the scripts and questions, can actually limit what we learn. That's where unstructured user interviews come in. Instead of sticking to a script, have open-ended conversations that let users share their thoughts and experiences freely. This can lead to unexpected insights that we might never have gotten with a traditional interview. Below are some tips that I find helpful during unstructured user interviews: 𝐋𝐞𝐭 𝐮𝐬𝐞𝐫𝐬 𝐠𝐨 𝐨𝐟𝐟 𝐨𝐧 𝐭𝐚𝐧𝐠𝐞𝐧𝐭𝐬. Sometimes the most interesting things people say come when they're not following a script. 𝐒𝐡𝐚𝐫𝐞 𝐲𝐨𝐮𝐫 𝐨𝐰𝐧 𝐟𝐫𝐮𝐬𝐭𝐫𝐚𝐭𝐢𝐨𝐧𝐬. If you're frustrated with something about your product, let the user know. This can help build trust and make them more likely to open up. 𝐀𝐬𝐤 𝐦𝐨𝐫𝐞 𝐪𝐮𝐞𝐬𝐭𝐢𝐨𝐧𝐬 𝐭𝐡𝐚𝐧 𝐲𝐨𝐮 𝐭𝐡𝐢𝐧𝐤 𝐲𝐨𝐮 𝐧𝐞𝐞𝐝 𝐭𝐨. The more you ask, the more you'll learn. Unstructured user interviews aren't about extracting information from users; they're about understanding their world. Treat each interview as an opportunity to learn something unique about your customers. You may not strike gold in every conversation, but you'll never find hidden gems if you stick to the surface. Let your users be great at being themselves, and focus on being great at your job – solving the problems they didn't even know they had.

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.

I didn’t win my first users with features. I won them with trust. Here’s how I built it. ✅ I don’t start with a pitch. I ask questions. “What’s your biggest struggle with content right now?” “What have you tried that didn’t work?” This helps me understand their world—before I even mention my product. ✅ I treat early users as collaborators, not just customers. Their feedback is gold. They tell me what’s confusing, what’s useful, and what’s missing. They help shape the product roadmap more than any spec sheet. ✅ I follow up personally. After someone uses the tool, I check in. “Was it smooth? Where did you get stuck? What would make it 10x easier?” These small touchpoints go a long way in building long-term trust. ✅ I’m transparent about what’s ready and what’s coming. I never overpromise. Instead, I say: “That feature isn’t ready yet, but we’re working on it—and I’d love your input.” In a world of automation, early-stage trust is still built one human at a time. If you’re building something new, don’t wait for perfection. Start conversations. You’ll build something better, and more importantly, you’ll build belief.

Ever started a conversation by asking someone their social security number? That’s what some usability tests feel like. 🕵️♂️🤦♀️ Getting users to open up takes time. And the right questions. Some things I’ve learned about running genuinely useful usability tests: 🕵️♀️ Tailor your pre-test questions to your research needs Don't just ask boring stuff like "How old are you?" Think about what background information will actually help you analyze your results. If you're testing a work tool, ask about company size or role. For a dating or networking app, (non-intrusive) questions about their social life might be a better fit. 🤖 Speak human, not robot Ditch the jargon! Instead of "Did the product's user interface facilitate ease of navigation?", try "Did you find it easy to move around the site?" Your users will thank you for not making them reach for a tech dictionary. 🎭 Go off-script (sometimes) Your discussion guide is a map, not a cage. If a user says something interesting, follow that thread! The best insights often come from unexpected detours. 🔜 Use clear tasks, not vague instructions Instead of saying "Explore the website," give specific, realistic tasks. For example, "Imagine you want to set up a new account. Please go through that process and tell me what you're thinking as you do." This approach mimics real-world usage and helps you identify specific pain points in your user journey. 🕳️ Spot the black holes in your UX Sometimes, the most important thing is what users don't do. If your "revolutionary" filter feature might as well be invisible - ask why. 🤔Ask 'why' "Why did you click there?" can reveal more than a hundred assumptive questions. It can also balance out the quantitative questions. If someone rates a feature 2 out of 5, ask what would have made it a 4 or 5. This combination gives you both the data to spot trends and the insights to understand the reasoning behind those trends. Here are my learnings on what makes a wildly successful usability test + an Airtable question bank that can help: https://bit.ly/4bODMJc How do you get your users to trust you during a usability test? What’s your go-to ‘human-ing’ warm-up question? #usabilitytesting

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.

I love how much enthusiasm and interest came from my last post on Jobs-to-Be-Done. But before diving into frameworks, I want to rewind and talk about some key fundamentals when it comes to customer discovery interviews. Because here’s what I’ve seen over and over again: Teams and founders get excited about an idea. They talk to people and show their prototype. People are kind and encouraging. And suddenly…it feels like validation. But polite nods and positive reactions aren’t actual validation. If you’re working on something new, your first job is to validate the problem, not the solution. And when you’re looking to validate the problem, here are some things to keep in mind: 1. Ask about the past Don’t ask people to imagine the future. Start with: “Tell me about the last time you …” That’s where the truth lives. When people are asked to predict the future, they’re often wrong. It’s Friday — did your week go exactly as you had predicted? 2. Avoid leading questions Skip the yes/no. Skip assumptions. People are often agreeable and may say “yes” — even when it’s not a real pain point. ❌ “Do you struggle with organizing student data?” ✅ “Walk me through how you organize student data today.” As they go through their story and you dig in, that's how you find the real struggle moments. 3. Dig into their story Don’t stick to a script. Get more context around the situation and follow the emotion. Bob Moesta calls it “following the energy” — when you hear a shift in tone or a moment that clearly mattered. Ask follow-ups like: “What happened next?” “Where were you? Who else was involved?” “What else have you tried?” That’s where the real insights live. 4. Look for signs of workarounds Spreadsheets, post-its, manual processes — all signs of friction. It’s in these struggle moments that valuable problems often appear. 5. Don’t pitch. Stay curious. Your mindset should be more like a journalist than a salesperson. You’re trying to understand, not convince. Be surprised. Be open to your assumptions being wrong. The Mom Test by Rob Fitzpatrick is a great getting started resource around this topic with even more tips. I’ll dive into JTBD frameworks soon, but this is the foundation that makes any customer discovery interviews more effective—especially when you’re building something new and innovative. Any others you’d add? #CustomerDiscovery #ProductDiscovery #JTBD #CustomerInterviews

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 👇

People often say what they think they should say. I had a great exchange with 👋 Brandon Spencer, who highlighted the challenges of using qualitative user research. He suggested that qual responses are helpful, but you have to read between the lines more than you do when watching what they do. People often say what they think they should be saying and do what they naturally would. I agree. Based on my digital experiences, there are several reasons for this behavior. People start with what they know or feel, filtered by their long-term memory. Social bias ↳ People often say what they think they should be saying because they want to present themselves positively, especially in social or evaluative situations. Jakob's Law ↳ Users spend most of their time on other sites, meaning they speak to your site/app like the sites they already know. Resolving these issues in UX research requires a multi-faceted approach that considers what users say (user wants) and what they do (user needs) while accounting for biases and user expectations. Here’s how we tackle these issues: 1. Combine qualitative and quantitative research We use Helio to pull qualitative insights to understand the "why" behind user behavior but validate these insights with quantitative data (e.g., structured behavioral questions). This helps to balance what users say with what they do. 2. Test baselines with your competitors Compare your design with common patterns with which users are familiar. Knowing this information reduces cognitive load and makes it easier for users to interact naturally with your site on common tasks. 3. Allow anonymity  Allow users to provide feedback anonymously to reduce the pressure to present themselves positively. Helio automatically does this while still creating targeted audiences. We also don’t do video. This can lead to more honest and authentic responses. 4. Neutral questioning We frame questions to reduce the likelihood of leading or socially desirable answers. For example, ask open-ended questions that don’t imply a “right” answer. 5. Natural settings Engage with users in their natural environment and devices to observe their real behavior and reduce the influence of social bias. Helio is a remote platform, so people can respond wherever they want. The last thing we have found is that by asking more in-depth questions and increasing participants, you can gain stronger insights by cross-referencing data. → Deeper: When users give expected or socially desirable answers, ask follow-up questions to explore their true thoughts and behaviors. → Wider: Expand your sample size (we test with 100 participants) and keep testing regularly. We gather 10,000 customer answers each month, which helps create a broader and more reliable data set. Achieving a more accurate and complete understanding of user behavior is possible, leading to better design decisions. #productdesign #productdiscovery #userresearch #uxresearch

We ask candidates to open up in interviews. “Tell me about a time you failed.” “What’s your biggest weakness?” “What would your last manager say you struggle with?” Most of us sit there, taking notes, nodding, expecting honesty; but how often are we honest with them? How often do we say, “Here’s where our culture is still a work in progress”? Or, “This team is strong in X, but we’re actively struggling in Y”? Interviews are supposed to be a two‑ way street, but too often they’re not. We demand vulnerability from people who need the job, and offer them nothing but curated talking points in return. When I started sharing the real picture, our strengths and our messier parts, I noticed something. Candidates leaned in. The conversations became richer. Most importantly, the people who joined knew exactly what they were signing up for. Honesty attracts the right people. Curated perfection doesn’t. #OpenToWork #Hiring #JobSearch

Before interviewing customers, learn how to interview customers. It’s a lot of work to get a customer on the phone. And if you have a poor interviewing technique, you won’t glean valuable information and could annoy some of your best customers. My years in sales and experience with customer interviews taught me that the trick isn't in what you ask but in how you listen. So, here are 3 subtle interview tactics that changed how I interview: 1️⃣ The mirror technique Don't just ask "tell me more." Instead, repeat their last few words and pose back as a question. Customer: "Your software is frustrating." ❌ "Oh, can you elaborate?" ✅ "Frustrating?" The customer will naturally open up without feeling interrogated. 2️⃣ Strategic silence When a customer starts rambling or gets heated, use silence to your advantage. Go quiet after the customer stops speaking and let the pause linger for 5-6 seconds. It feels awkward, but that's the point. This works by: ➖Regaining control of the conversation ➖Giving angry customers space to reset ➖Steering the discussion back on track 3️⃣ Detailed validation Instead of the generic "got it" responses, prove you're listening: "So what I'm hearing is [specific point 1], [specific point 2], and [specific point 3]. Did I capture that correctly?" People want to feel that they are heard and love when someone proves that they are listening. This builds trust fast. Great customer insights don't come from asking perfect questions. They come from listening and knowing how to use that information to guide the conversation.