The Art of Not Leading the Witness

This is what’s going on in most founders’ heads during discovery calls - they desperately want to be right.

You've got this brilliant solution. You just need customers to confirm it's their biggest problem. So you schedule calls, armed with leading questions to extract the validation you crave.

"This is a huge problem for you, right? Tell me more about how painful this is. From 1-10, how much time do you waste on this? When you think about your biggest challenges, this has to be near the top?"

Congratulations. You've just wasted everyone's time.

Alexa Grabell, co-founder and CEO of Pocus, whom I chatted to about this, learned this the hard way. Early on, she'd guide conversations toward her hypothesis.

People would nod along, agree, even sound enthusiastic. But when it was time to buy - crickets.

Why?

Because people are nice. When a founder presents their baby most people won't say it's ugly. They'll say something polite. Or even convince themselves it might be useful. But this isn't product-market fit.

The fix:

Start every conversation with genuinely open questions.

Not "tell me about your data problems" when you're building a data solution. Instead: "What are the top three things keeping you up at night?"

Then shut up and listen.

If your solution isn't in those three, you've learned something valuable.

If it is, let them bring it up in their own words without prompting.

The difference is stark. When you lead the witness, you hear what you want. When you lead with curiosity, you hear what you need.

Here's how to structure discovery calls:

1. Set hypotheses—but keep them to yourself. Write it down. Test whether reality matches your assumptions. But never let them leak into your questions.

2. Ask about priorities, not problems. Everyone has problems. Not everyone prioritizes fixing them. You need to know what matters enough to drive action.

3. Probe for why. When someone mentions a challenge, dig deeper. Why is it a challenge? Why haven't they solved it yet? Why does it matter to their business? eal insights hide 3 questions deep.

4. Track patterns, not anecdotes. One person saying your problem is critical means nothing. Nine out of ten saying it unprompted? Now you're onto something.

5. Be comfortable with being wrong. Every hypothesis that gets shattered saves you months of building the wrong thing. Celebrate the calls that destroy your assumptions and save you time.

The hardest part while doing so?

You quit your job, convinced investors, recruited co-founders—all based on a vision. Having customers tell you that vision is wrong feels like failure.

But it's not. It's education.

The faster you learn, the faster you’ll find out what your customers actually want.

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Enjoyed reading this?

Then check out my conversation on the focal podcast with Alexa Grabell, Co-founder and CEO of Pocus ($23M raised from First Round, Coatue, Pear, Box Group, GTM Fund).

Youtube | Apple Podcast | Spotify

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