How to run a problem interview

A specific script, the questions that work, and the ones that quietly destroy your data.

What is it?

A 25–30 minute conversation about how the person's work actually goes today. You do not describe your product. You ask about specific past events.

The structure: context → last time it happened → what it cost → what they tried → what happens next.

Why does a founder care?

Because unstructured conversations produce encouragement, and encouragement feels like evidence. People are kind, especially to someone visibly excited.

A structured interview about past behaviour is much harder to distort. 'What did you do last Tuesday' has an answer that exists independently of how the person feels about you.

Example

The script:

  • 'Walk me through how you handle [area] at the moment.' — open, no assumptions.
  • 'When did you last do this? Tell me about that specific time.' — anchors in a real event.
  • 'What was annoying about it?' — let them name the pain rather than confirming yours.
  • 'How long did it take? What did it cost you?' — quantifies.
  • 'Have you tried to fix this? What happened?' — the most valuable question on the list.
  • 'What happens if it stays like this?' — tests severity.
  • 'Who else deals with this? Could you introduce me?' — compounds the whole exercise.

    • Question 5 is the one that matters most. If they have tried to fix it — searched for a tool, built a spreadsheet, hired someone, paid for something and abandoned it — that is real evidence of pain. If they have never tried anything, it is an annoyance, not a problem worth a company.

    Questions that destroy your data:

  • 'Would you use a tool that did X?' — hypothetical, and they will say yes
  • 'Don't you find it frustrating when…?' — you supplied the answer
  • 'How much would you pay for this?' — people cannot price things that do not exist
  • 'Does that make sense?' — invites agreement, not information

    • The common mistake

    First-time founders pitch within the first three minutes. It is very hard not to — you are excited and it feels rude to withhold. But the moment they know what you are building, they start being helpful about your idea instead of honest about their life.

    Second: only talking to people who already like you. Friends and supportive contacts will confirm anything. You need people with no stake in your feelings.

    Third: not asking for introductions. Question 7 is how ten interviews become forty without any additional prospecting.

    How it works

    Step 1: Say the framing up front

    'I'm researching how people handle X. I'm not selling anything and I'd love to hear how it actually works for you.' This gives them permission to be blunt.

    Step 2: Anchor every question in a past event

    'The last time', 'that specific occasion'. Never 'usually' or 'would you'.

    Step 3: Stay quiet

    Aim to speak less than a quarter of the time. Silence after an answer usually produces the most useful sentence in the conversation.

    Step 4: Ask what they tried

    The single strongest signal. Effort already spent is evidence that words cannot fake.

    Step 5: Never pitch, even at the end

    If they ask what you are building, say you are still figuring it out and offer to show them later. Then actually do.

    Step 6: Ask for two introductions

    At the end, always. This is how the sample grows without cold outreach.

    When to use this

    Throughout validation, and periodically for ever. Aim for a floor of three a week early on.

    When not to use it

    This is not the script for a sales call or a usability test. Once you have a product and are trying to sell it, use a discovery call instead — different goal, different questions.

    Do this now

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