J. Marsh
Lead Editor, Startup & Product
Updated
Good interview questions get customers talking about their world. Bad ones get them complimenting your idea. The questions below are organized by interview stage and designed to surface evidence, not opinions.
Opening questions
Walk me through your role and what a typical week looks like. Tell me about the last time you ran into [problem area]. What were you trying to get done?
These questions anchor the conversation in concrete, recent events instead of abstractions.
Problem questions
How often does this come up? What did you try? What did you end up doing? What was that worth to you in time or money?
Pay close attention to workarounds. They reveal both pain and budget.
Alternative and substitution questions
What tools, services, or people do you currently use? What do you like and dislike about them? If they disappeared tomorrow, what would you do?
Closing questions
Who else struggles with this? Can you introduce me to two of them? What would have to be true for you to switch?
Key takeaways
- -Anchor every question in a recent, concrete event
- -Listen for time spent, money spent, and unprompted emotion
- -Ask for referrals; warm intros compound
- -Never pitch your solution in a problem interview
Frequently asked questions
- How long should an interview be?
- Thirty minutes is plenty. Most insight lands in the first 20.
- Should I record?
- Yes, with permission. Notes alone miss tone and exact phrasing, which are gold for messaging.
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