The courage to ask the wrong question

We’ve all been there. Sitting in a meeting, listening, nodding... and quietly wondering, What does that mean? But instead of raising a hand, we stay silent. We want to appear prepared, informed, confident.

I’ve done it too. More than once, I’ve let pride win. I’ve swallowed my question, hoping the answer would magically appear.

It never does.

Over time, I’ve noticed something. The people I admire most are the ones who move through complexity with ease. They connect ideas and people effortlessly. And they ask more questions than anyone else. They want to know more.

They’re curious. Deeply curious. They’ve learned to quiet their ego and ask. Even if the question sounds obvious. Even if someone might raise an eyebrow. They don’t wait for the perfect moment or the perfect phrasing. They just ask.

If you ask enough questions, the right ones begin to show up.

Not by chance. But because curiosity works like a compass. It doesn’t need to know the whole map. It only needs to point in a direction.

There’s grace in saying, I want to understand. A quiet confidence in not pretending. In asking without fear of looking foolish.

The myth of the person who always has the answer is still alive and well. But the people who actually make progress, the ones who bring clarity and connection, are the ones who ask the questions no one else dares to ask.

Questions open doors. They spark conversations. They show who’s really paying attention. They build bridges where there were none before.

Some questions impress. Some challenge. The most powerful ones come from genuine curiosity.

Start there.

The first ones might feel clumsy. That’s fine. Every question moves you a little closer to what matters. With each one, you sharpen your understanding. You peel back a layer.

And slowly, your questions evolve. They become sharper. They touch deeper places. You start to notice patterns. You find people who want to be asked. People who light up when they feel seen and heard.

When you bring thoughtful questions to the right people, the answers have a way of finding you.

This is about practice. And courage.