“Tell me about the last time you tried to solve this problem. Walk me through what actually happened.”
From Teresa Torres · Product discovery coach · author of Continuous Discovery Habits
Why it works
People are unreliable narrators of their own behavior in the abstract — they generalize, rationalize, and tell you the version of themselves they wish were true. Anchoring to one specific, recent episode collapses that distortion: a real memory has texture, sequence, and friction the person can't invent on the spot. Teresa's insight is that a single concrete story yields more durable insight than ten satisfaction ratings, because it exposes the actual job, the workarounds, and the moments where the current solution failed.
When to ask
Early in a discovery interview, once you have surfaced the opportunity you want to explore but before you propose any solution. Use it whenever you catch yourself about to ask 'would you' or 'do you usually'.
Good follow-ups
- What did you do right before that? And what happened next?
- What were you hoping would happen?
- Who else was involved, and what did they do?
Watch out for
Letting the person drift back into generalities ('I usually just…'). The moment you hear the present tense or 'usually', gently pull them back to the specific instance: 'Sorry — the last time specifically, what did you do first?' Also avoid stacking it with a hypothetical; one whiff of 'would you' and the story collapses into speculation.
Where to ask
- User interviewgreat
Built for the live back-and-forth — the value is in the follow-ups that pull a drifting answer back to the specific instance.
- Support chatworkable
Works when a conversation is already open and you can probe in the moment; weaker as a cold opener.
- In-product surveypoor
Without a moderator the story collapses into generalities; ask for the episode in a single concrete question instead.
Reworded for this context: “When did you last try to solve this, and what did you do — step by step?”
- Long-form surveypoor
No way to redirect 'I usually just…'; the open prompt yields tidy summaries, not the textured account this question exists to get.
Pairs well with
Stage: Start · A question popularized by Teresa Torres