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Customer conversations that tell you the truth

The moment you describe what you are building, the conversation becomes a performance. Ask about the last time the problem happened instead, and everything you hear is a fact.

24 October 2026 · 5 min read

Twenty is not a magic number, but it is roughly where patterns start repeating. Below ten you are hearing individuals. Somewhere around twenty you start hearing the same complaint in different accents, and that is the thing you are looking for.

The rule that makes these conversations useful

Do not talk about your idea. Talk about their life. The moment you describe what you are building, the conversation becomes a performance: they are now evaluating you, being encouraging, and telling you what they think you want to hear. Everything after that is contaminated.

Instead, ask about the last time the problem happened. Specific, recent, already in the past. Past behaviour is a fact. Future intention is a guess.

Questions that work

  • Tell me about the last time this happened. What did you do?
  • How often does that come up?
  • What did you try before? Why did you stop?
  • Who else is involved when this goes wrong?
  • What does it cost you when it happens? Time, money, or someone being annoyed with you?
  • What are you doing about it at the moment?

Questions that do not

  • Would you use something that did this? They will say yes.
  • Do you think this is a good idea? They will say yes.
  • Would you pay for this? They will say yes, and then not pay.
  • How much would you pay? They have no idea, and the number they invent will mislead you for months.

How to get the conversations

Start with people you already have some connection to, because the reply rate is the difference between this taking a week and taking two months. Former colleagues. People in groups you belong to. Anyone who has asked you for help before. Then work outwards to strangers.

Keep the ask small and honest. You are not selling, you are asking for fifteen minutes about how they handle a specific thing. Say that plainly, say why you are asking them in particular, and offer to send them what you learn. A surprising number of people say yes, because almost nobody asks them about their work with genuine interest.

The message that gets replies

Short, specific, no pitch, and obviously written for them. Something close to this, in your own words:

Hi Dalia. You run two sites and I remember you mentioning the stock ordering being a weekly headache. I am looking into how independent places handle it and I am trying to speak to a few people who actually do it. Fifteen minutes, no pitch, I am not selling anything yet. Happy to send you what I learn from the others. Any chance this week?

Four things are doing the work there. It names a specific thing she said. It asks for a defined, small amount of time. It says plainly that there is nothing to buy. And it offers something back. Remove any one of them and the reply rate drops.

What does not work: a paragraph about you, a calendar link in the first message, the word opportunity, and anything that reads as though it was sent to forty people. It was sent to forty people, but it should not read that way.

How to run the fifteen minutes

  1. 01Say again that you are not selling, then stop talking. The first minute sets whether this is a conversation or a pitch.
  2. 02Ask about the last time it happened, and let them tell the story badly. Do not tidy it up for them.
  3. 03Follow the specifics. When they say it is a nightmare, ask what happened the last time it was a nightmare. The anecdote is the data.
  4. 04When they ask what you are building, give one honest sentence and return the question. Answering at length ends the useful part.
  5. 05Close by asking who else you should speak to. This is how twenty conversations become possible.

Keep it to the time you asked for. Finishing early is better than overrunning, and it is the reason the next person says yes when they hear you were straightforward with the last one.

What to write down

After each conversation, write three things while it is fresh: the exact words they used for the problem, what they currently do about it, and whether they have ever spent money on it. The exact words matter more than you think. They become your page, your emails, and the headline somebody eventually clicks.

When the answers contradict each other

They will. Five people will describe the problem one way and four another, and the temptation is to build something that serves both. Resist it. Contradictory answers usually mean you are talking to two different buyers who happen to share a job title.

Sort the notes into the two groups and look at what separates them: size, who does the work, whether they have been burned before. Then choose one group. Serving two buyers badly is the most common way a clear offer turns to mush, and it almost always begins as an attempt to be fair to the research.

Work to do

  • Make a list of twenty names. Not categories. If you cannot reach twenty, you have chosen a buyer you have no access to, which is worth discovering now rather than later.
  • Send the first ten messages, each one naming something specific about that person.
  • Run at least three conversations and write down the exact words each person used for the problem.
  • Ask every one of them who else you should speak to, and add those names to the list.

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