100 Coffees

100 Coffees

The Richest People I Know Ask Better Questions

Sequoia Taylor's avatar
Sequoia Taylor
Jun 28, 2026
∙ Paid

One of the biggest surprises of my professional life is that the most successful people I’ve met rarely seem obsessed with having the answers.

They’re obsessed with asking better questions.

That sounds like something you’d read on a motivational poster, which is unfortunate, because it’s also true.

When I was younger, I assumed expertise looked a certain way. I thought it meant walking into a room and knowing things. Having strong opinions. Having answers. Being decisive. Being the person everyone else looked to when something complicated needed to be explained.

Sometimes expertise looks like that.

But over time I started noticing a different pattern. The people who consistently made the best decisions were often the people who spent the most time asking questions.

Not performative questions. Not “look how smart I am” questions.

Real questions. Questions that helped them understand what everyone else was missing. Questions that revealed assumptions. Questions that exposed blind spots. Questi…

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