On asking questions

Most people think intelligence is about having answers.

It can be. But more often it’s about asking better questions than everyone else.

For a long time, I optimized for sounding sharp. In meetings, interviews, early startup conversations. I wanted to be the one with the crisp framework and the quick take. Speed felt like competence.

What I didn’t realize is that speed is often the enemy of truth.

Answers look impressive. They create the feeling of momentum. Questions feel slower. More exposed. In a culture that rewards confidence theater, uncertainty gets mistaken for weakness.

That’s backwards.

The people who change outcomes rarely do it by knowing more facts. They do it by framing the problem differently. And framing is mostly a matter of asking the right question at the right time.

There is such a thing as a dumb question.

If you listen carefully, you’ll notice that many questions fall into a few predictable types.

Some are performative. They’re statements wearing question marks. The asker isn’t trying to learn; they’re trying to signal intelligence or alignment.

Some are defensive. They quietly narrow the discussion to safe ground. “Let’s talk about what I already understand.”

Some are lazy. They outsource thinking. They exist because silence feels uncomfortable.

None of these move the room forward.

Good questions do something slightly dangerous. They destabilize assumptions. They slow things down when everyone else wants to speed up. That’s precisely why they matter.

Here’s a useful rule: every question hides a fear, a goal, or a belief.

When someone asks, “What features should we build next?” they’re often really asking, “How do we avoid being wrong?”

When a founder asks, “How do we grow faster?” it sometimes means, “Why aren’t we winning yet?”

If you answer the surface question, you help a little. If you answer the one underneath, you change direction.

This is why the best question-askers can seem almost psychic. They’re not necessarily smarter. They’re more willing to name what everyone else is optimizing for but hesitant to say out loud.

Startups are especially bad at this.

They celebrate speed and romanticize conviction. Doubt feels like drag. So teams rush to execution before they’ve achieved clarity.

I’ve seen talented teams spend months building the wrong thing, not because they lacked skill, but because they never asked the uncomfortable questions early enough.

Who exactly is this for?

What pain does this replace, not just add to?

What problem are we actually solving?

Instead, they ask safer ones.

Can we ship by Friday?

How should we position this?

Can marketing fix it?

These optimize for motion, not direction. Motion without direction just burns time.

One question kills more products than bad execution ever will: “What problem are we actually solving?”

Not the pitch-deck version. The real one.

It feels basic, almost embarrassing to ask. That’s why it’s dangerous to skip. When you don’t ask it, you can become very good at executing the wrong idea.

A sharper version is: “What would make this unnecessary?” That question reveals whether you’re addressing causes or just symptoms.

Not all questions are equal. Some add information. Others multiply it.

“What would have to be true for this to fail?” invites reality into the room.

“Who is this not for?” forces clarity through subtraction.

“What are we assuming without evidence?” protects you from building on air.

“What decision does this inform?” filters noise from signal.

Smart people are often the worst at this. Knowledge becomes identity, and identity needs protection. Bad questions protect status. Good questions risk it.

This is why junior people sometimes ask the most powerful questions in the room. They aren’t yet invested in being right.

Leadership, at its core, is not about having answers faster. It’s about creating clarity.

Instead of “Why did this fail?” try “What signal did we miss?”

Instead of “Who made this decision?” try “What constraints shaped it?”

These questions don’t assign blame. They improve the system.

There’s one more piece that’s underrated: silence.

Asking a good question and then filling the space immediately defeats the point. Silence is where most people panic. They rush to rescue the room with commentary.

Don’t.

Ask the question. Then wait.

If you want to practice this, try something simple for a week. Notice the first question that comes to mind in a conversation. Then ask the one underneath it instead.

You’ll feel slower. Slightly exposed. That’s a good sign.

The art of asking questions isn’t really about curiosity. It’s about humility—the recognition that reality is usually more complicated than your current model of it.

The fastest learners don’t chase better answers.

They design better questions.

That’s where leverage comes from.