How a conversation gets contaminated
The person opposite you wants to be helpful and doesn't want an awkward conversation. Given any signal about what you're hoping to hear, most people will move toward it — not dishonestly, just socially. Your enthusiasm is a signal. So is the order of your questions.
| Leading | Neutral |
|---|---|
| "Would a tool that did X be useful?" | "Walk me through the last time you did X." |
| "Is this frustrating?" | "What happened next?" |
| "How much would you pay for this?" | "What do you spend on this today?" |
| "Do you think you'd use this weekly?" | "How many times did you do this last week?" |
| "We built this to fix that — thoughts?" | (ask nothing about your product until the end) |
Ask about the past
People are unreliable at predicting their own future behaviour and reliable at recounting what happened. "Would you use this?" is a guess offered politely. "What did you do last Tuesday?" is a fact.
- "Tell me about the last time this came up." — anchors to a specific event with real detail in it
- "How long did that take?" — turns a vague annoyance into a number
- "What did you use?" — reveals the workaround, and often the budget already being spent
- "What did you do when it went wrong?" — finds the part that actually hurts
- "Have you looked for something better?" — a yes is unmet buying intent, which is the strongest early signal there is
Notice that none of these mention your product. A complete, useful interview can happen without the other person ever learning what you're building — and those are usually the most informative ones.
Getting past the first answer
First answers are summaries, and summaries have had the useful detail removed. Three cheap techniques get past them.
- SilenceWait three seconds after they finish. Most people continue, and the second half is usually more specific and more honest than the first.
- "Tell me more about that"Neutral, contains no hypothesis, and works on almost any answer.
- Repeat their last few words as a question"It just takes forever?" invites elaboration without suggesting a direction.
- Ask for the specific instanceWhen someone speaks in generalities — "we usually…" — ask about the most recent actual occurrence.
What an answer is worth
| Answer | Worth |
|---|---|
| "That's a great idea" | Nothing — it's politeness |
| "We built a spreadsheet for that" | High — an existing workaround they maintain |
| "I'd definitely use it" | Low — a prediction about the future |
| "We pay someone to do it now" | Very high — a budget already exists |
| "Send me something when it's ready" | Low — a polite exit |
| "Can I show this to my colleague?" | High — they're spending their own credibility |
One useful discipline: after each conversation, write down what would have to be true for you to be wrong, and whether this conversation moved that. Interviews that only ever confirm you are interviews being run badly.
Common mistakes
- Pitching in the first five minutes and treating everything after as data
- Asking whether someone would use something, rather than what they did
- Filling silences, which are where the useful half of the answer lives
- Recording your interpretation rather than their phrasing
- Counting compliments as validation
Key takeaways
- Any signal about your hopes moves the answers; enthusiasm is a signal
- Past behaviour is fact, future intention is a polite guess
- Silence, "tell me more", and asking for the specific instance get past summaries
- Existing workarounds and existing spend are the answers that count
Try it yourself
Write your interview script, then cross out every question that mentions your product or contains the word "would". Run what's left. It will feel too short and produce more than the original.