Crafting Open-Ended Questions For User Experience Interviews

CSMs, are we asking the right questions? 🤔 Sometimes, we stick to surface-level questions that don’t really get to the heart of what our customers need. But small tweaks can lead to big insights. Here’s how to take your customer conversations from basic to brilliant: Go from: "Are you happy with the product?" ➡️ To: "Can you share a specific example of how our product helped you achieve a recent business goal?" Asking if someone is happy only scratches the surface. The better question digs into the value they get from the product and how it ties into their success metrics. Go from: "Do you have any issues with the product?" ➡️ To: "Can you walk me through a recent challenge you faced while using the product and how you worked around it?" A yes/no question limits feedback. Asking for a specific experience helps you understand user pain points and provides actionable data. Go from: "What features do you like?" ➡️ To: "Which feature did you use most often this past week, and how did it help your team?" It’s not just about what customers like; it's about what creates the biggest impact for their team. Go from: "What are you concerned about during your next board meeting?" ➡️ To: "What key metric are you most focused on reporting to your board next quarter?" Asking this question helps you understand your customer’s priorities and where your product can help them deliver on their goals. Go from: "What metrics are you held accountable to in your specific role?" ➡️ To: "Which metric has been most challenging for you to hit, and how can our product help improve it?" This question shifts the focus to their pain points, giving you a chance to help them leverage your product to overcome obstacles. Go from: "Are there aspects of our product that you feel you are not fully utilizing yet?" ➡️ To: "Is there a feature of our product that you haven’t fully explored but think could be valuable for your team?" This specific question gets customers thinking about how to get more value from your product and where they might need help to unlock new features. --- These updates give you more than answers. They push deeper talks that lead to useful ideas and better connections. What’s one question you plan to improve in your next customer conversation?

5 research questions that uncover what users won’t say out loud. Polite answers won’t build great products. These questions are the ones that force people to think and lead to useful product insights: 👉 “Tell me about the last time you tried to do [task] and gave up.” People don’t bring up failure unless you ask. But when they do, they show you where your product actually breaks 👉 “Is there anything in [product] without which you won't use it?” Reveals true dependencies vs. nice-to-haves. Users will tell you the one thing holding their workflow together. It’s rarely what you expect. 👉 “Walk me through what you were thinking during that 30-second pause.” Ask this in the moment, not after. It surfaces hesitation, mental model gaps, and quiet confusion that observation alone won’t catch. 👉 “What’s something about this that didn’t behave as you expected?” This is great for spotting subtle friction that users may not verbalize on their own 👉 “What’s the workaround you’ve created for this?” People invent hacks to survive broken flows & that can be gold.  Workarounds show what users need but can’t articulate. What’s the one question you always ask no matter what?

Some of my favorite customer moments come from a simple shift: asking open-ended questions and letting the conversation breathe. I do come to meetings with a checklist and goals to “accomplish” during the discussion. But over time, I realized I was missing something important: the customer’s story, in their own words. Closed-ended questions brought a lot of polite “yes” answers and head nods, but rarely led to a breakthrough. Sebastien Waltzing left a comment on one of my recent posts and got me thinking about the real magic that happens when we invite customers to share their view of value. Questions that cannot be answered in a single word often trigger a pause, and then a deeper look at what matters most on their side of the table. Here’s what I try now: Instead of, “Are you satisfied with the feature?” I’ll ask, “How does this feature change the way your team hits its goals?” Or, “What results would make this an absolute win in your book?” Conversations like these do more than just fill out a quarterly or strategic review. They turn customers into collaborators. We hear about unexpected wins, real struggles, and big ambitions. We learn where to invest next. So, my challenge to every customer success leader: pause your agenda, and let the customer lead for a moment. You will not just confirm value. You will co-create it. What is one open question you have seen spark a real, eye-opening answer from your customers? I am always looking to add new ones to my toolkit.