Asking more incisive questions during customer interviews is a skill you can learn and strengthen. | Photo by Jodi B Photography
20 questions to uncover what your customers are not saying
What is the hardest thing about customer interviews? It is not the logistics. You can find the time to schedule a few calls. And it is not the format either — templates exist to help with planning and scripting. I think the hardest part is psychological. It feels risky to ask bold questions when you are not sure you want to hear the answers.
You are not just asking questions. You are also confronting your own assumptions about what customers need and why.
That discomfort can make you cautious. You stick to the script. Follow-up questions become a formality rather than a pursuit of deeper truth. And if a response feels vague, you move on — instead of pressing for clarity. The conversation ends with a tidy summary, but few fresh insights.
It is a natural impulse. Time is tight, and deadlines demand momentum. So you lean on what feels efficient: a familiar set of prompts, assumptions shaped by prior interviews, your own mental shorthand for what customers probably mean. But that approach ends up revealing more about your thinking than theirs.
Most of us were never taught the layered skills of interviewing. Building rapport. Listening for nuance. Knowing when to pause, rephrase, or change direction. These are subtle skills that require practice.
The best interviews feel less like information-gathering and more like joint investigation — a way to surface what customers have not yet put into words.
When we built Aha! Discovery, we revisited how we conduct interviews. We refined the questions we ask, tracked patterns across conversations, and challenged each other's interpretations. That work became the foundation for what we built: a tool that helps product teams guide meaningful research and link insights directly to product direction.
Here is a set of 20 questions to help you do the same. Each one is drawn from real use, designed to prompt honest answers and uncover what customers might not yet have said out loud.
Exploring new product opportunities
Early discovery is about deciding what to build before you commit to development. You are investigating where customers struggle and why. People may not be able to name their challenges directly, so your job is to guide them there.
Ask questions such as:
When do you feel most annoyed or frustrated during your workday?
What is something your team avoids because it is just too messy or manual?
What slows you down when you are trying to do your most valuable work?
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Solving customer pain points
When customers are frustrated or something is broken, it is an opportunity to learn. Show empathy. Then, explore what led to the issue — whether it was a flawed feature, clunky experience, or mismatch with real needs.
Try questions like:
Can you show me the exact moment when things started to feel off or confusing?
That is annoying. What were you trying to do when that happened?
What did you expect to happen instead?
If you were onboarding someone new, what would you warn them about when using this part of the product?
What workarounds does your team use to solve this issue?
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Defining complex new functionality
Say the team is gearing up to build a major new feature. There may be several viable directions. The goal is to understand how people would actually use the functionality. Let them describe their goals in detail. Then, tailor follow-up questions to clarify how they work today and what they would change.
Ask things like:
What would make you hesitate to use this functionality — even if it technically works?
What is a small feature or capability that actually makes a big difference to your team?
When you try to get this done today, what is the very first step you take?
If this functionality existed today, how would it change your workday?
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Designing smarter workflows
When reviewing a complex process, focus on how work actually gets done. Ask about the sequence of steps, how people navigate uncertainty, and where bottlenecks emerge. You are trying to understand your customers' world — not just their interactions with your product.
Consider questions like:
Was there a point where you felt unsure about what to do next?
What did you expect would happen next?
Is there a step you would skip, automate, or delegate?
What would you do differently if you could modify this workflow?
Where in the process would someone unfamiliar with your workflow get stuck?
How do you usually double-check that you have done this right?
How do you know when the process is complete?
Can you describe what the ideal way to do this would look like for your team?
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Asking incisive questions and digesting uncomfortable feedback is essential to strong product discovery.
Creating a dialogue with your customers takes openness and real curiosity. Be prepared to ask "why" multiple times and in different ways. Request examples. Rephrase what you heard. Let people sit with the question and elaborate. When you build this kind of dialogue, you move closer to insight — and delivering something truly useful.
Link the voice of the customer to product decisions and the roadmap. Try Aha! Discovery today.
