You’ve done it. I’ve done it. Everyone building something has done it.

You post your idea, your landing page, your demo. You ask “would you use this?” or “does this solve a problem for you?”

Everyone says yes.

You feel validated.

You learn nothing.

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The Problem With Hypothetical Questions

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“Would you use this?” is a hypothetical. It costs the person nothing to say yes. They’re imagining a future version of themselves in a future situation where they might need this thing.

That person isn’t real. Their answer isn’t real.

What you need is behavior, not intention. And behavior only exists in the past.

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The Question That Actually Works

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“Walk me through the last time you dealt with [the problem].”

Now they have to recall a real event. They can’t answer with a hypothetical. The story that comes out tells you more than a hundred survey responses.

Here’s what you learn that the first question never gives you:

1. What they actually did — not what they think they’d do

People who say they’d pay for a productivity tool already have a workaround. A spreadsheet, a Slack thread, a habit they built. They’re not planning to give it up. You only find that out by asking what they actually did last time.

2. What you’re really competing with

It’s almost never another product.

It’s “I just do it manually.” It’s “I ask my assistant.” It’s “I gave up and it never got done.”

Knowing the real alternative tells you what your bar actually is. You’re not competing with another SaaS — you’re competing with the path of least resistance.

3. Whether the problem is painful enough

If they struggle to recall the last time it happened — it’s not a burning problem. They won’t switch for it.

If they light up, lean forward, and tell you three stories — you have something.

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The Follow-Up That Becomes Your Roadmap

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After they tell you the story, ask: “What did you do next?”

Keep asking it. They’ll describe a chain of workarounds — the thing they tried first, the thing they fell back on, the step where they gave up.

That chain is your product roadmap. Each workaround is a step you could remove.

"Walk me through the last time you had to reschedule a meeting across three people." → "I went to my calendar..." → "What did you do next?" → "I checked their availability manually..." → "What did you do next?" → "I sent three separate messages..." → "What did you do next?" → "I waited two days and one person never replied so I just picked a time."

Every “what did you do next” reveals a friction point. You didn’t have to guess at them.

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The Trap Most Builders Fall Into

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The “would you use this?” question feels like validation because people say yes. It’s actually a trap — it filters for politeness, not pain.

The “last time” question feels riskier because it might reveal that the problem isn’t bad enough to solve. But that’s information. Better to learn it in a conversation than after six months of building.

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A Framework for Better Research Questions

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Instead of --> Ask Would you use a tool for X? --> Walk me through the last time you did X Is X a problem for you? --> How often does X come up? What did you do last time? Would you pay for this? --> What have you already tried? What did it cost you? Does this solve your problem? --> What did you do instead? Why didn’t that work?

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The Real Signal

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A return visit to your product after a week tells you more than any survey answer. But you don’t always have a product yet.

The “last time” question is how you get real signal before you build anything. It points at something that already happened — something that can’t be spun or optimized for politeness.

One conversation like this is worth more than a hundred “would you use this?” responses.

Go find one person. Ask them about the last time. See what you learn.