The art of asking questions that actually matter

They create a false sense of certainty, the kind that looks good in a slide deck but collapses under market reality. We all tend to ask questions that make it easy for people to agree with us. 

Founders ask, “Would you use this product?” 

VCs ask, “Is this market growing?” 

Marketers ask, “Would you be interested if we launched this feature?” 

These are comfort questions. They feel like diligence, but they’re really narrative reinforcement. 

Good questions dig into behaviour, not opinion. 

Instead of asking if someone would use your product, ask when they last tried to solve this problem and how. 

Instead of asking if the market is big, ask who is paying today and how much. 

Instead of asking if a founder is prepared, ask how they’ve navigated the last blind corner and what broke along the way. 

Reality lives in specifics: actions, transactions, frustrations. That’s where the signal hides. 

False comfort, real consequences 

For VCs, the temptation is to validate an investment thesis with shallow diligence: 

“The TAM is clearly massive.” 

“This founder has charisma.” 

“Everyone’s talking about this space.” 

But the right diligence questions feel less glamourous and more uncomfortable: 

How many customers are paying, at what gross margin, and how fast is that improving? 

What are the real switching costs in this market? 

If demand is real, what bottlenecks are already visible in delivery? 

The answers might make you less excited, but that’s the point. Good questions protect you from falling in love with a mirage. 

A discipline, not a trick 

The Granny test isn’t about clever phrasing. It’s about intellectual honesty. Founders must resist the urge to chase flattering answers; VCs must resist the urge to justify consensus narratives. Both must trade easy optimism for hard evidence. 

Because whether you’re building or funding, asking bad questions is like running negative margins: it feels like growth, but it’s just deferred collapse.