Good interview questions share three traits: they are about the past, they are open, and they do not reveal the answer you are hoping for. Everything else is variation.
The core set
- "Walk me through the last time this came up."
- "What did you do about it?"
- "What did that cost you — money, time, or hassle?"
- "What else did you try before that?"
- "What happens if you do nothing?"
- "Who else is affected when this goes wrong?"
- "What is the most frustrating part of how you handle it today?"
Notice that none of them mention your product. The moment you describe what you are building, the conversation stops being research and becomes a demo.
Ask "why" until it gets uncomfortable
The first answer is almost always a surface answer. Two or three follow-ups gets to something real, and the third "why" is usually where the interesting thing lives.
"We need better reporting."
Why? "Because I spend Mondays building the same deck."
Why does that matter? "Because I am doing it instead of talking to clients."
So the cost is...? "Probably two client conversations a week. That is the real cost."
That last sentence is the one worth building around, and it took three questions to reach.
Leading questions to avoid
- "Don't you find X frustrating?" — you have supplied the feeling.
- "Would it help if...?" — you have supplied the solution.
- "How important is X on a scale of one to ten?" — invented precision about a hypothetical.
Try it
Write your interview script using only past-tense, open questions. Read it back and delete any question that hints at what you want to hear.