Ask about the last time, not the perfect future

Invite a specific story

Ask someone to describe the last time they encountered the problem you are investigating. Where were they? What triggered the task? What happened next? A recent example gives both of you something concrete to examine.

Follow the sequence

Let the person walk through the experience before presenting a solution. Notice the tools, people, and pauses involved. Ask what they did when something failed and which part required the most effort. The order of events can reveal a constraint that a feature wish list misses.

Keep interpretation separate

Write the person’s observation in one place and your interpretation in another. “I asked a colleague where the file was” is an observation. “The team needs a new search product” is a hypothesis. Keeping the distinction visible makes later decisions easier to challenge.

Close with permission and context

Explain how you intend to use the notes and ask before recording or sharing identifiable details. In a team review, use only the information needed to discuss the problem. Do not turn a single conversation into a statistic or imply an endorsement.

Bring the observations into the one-page founder story. The next useful step may be a smaller prototype question, not a longer feature list.