On Asking Better Questions

Photo by Kathya Meza on Unsplash

The quality of our questions determines the quality of our life.

That line sits at the top of a spreadsheet in my Google Drive. A quiet collection I’ve been adding to for years, questions gathered from conversations, books, articles, passing threads.

Questions like:

Who am I when I am uninterrupted?

Where are you wanting to take without fully giving?

What problem do I solve with more ease than most?

I journal every morning. When I feel stuck, short on clarity, energy, or depth, I open it and challenge myself to think more carefully about what’s actually going on.

I started my career as a journalist. That taught me something I’ve never stopped thinking about: the difference between a question that extracts information and one that opens something up. Between a clever question and a well-timed one.

It also taught me the value of silence. Of sitting in the gap of a conversation and waiting. That’s often where the most interesting things surface.

But getting there requires preparation, and not just of the question itself. What matters more is preparing the person you’re asking. Allowing them to feel ready to respond.

Even a strong question falls flat if that readiness hasn’t been created. I’ve watched it happen. The right words, wrong moment. A tangent that runs slightly too long, and suddenly the same question lands completely differently.

Recently, a project I was involved in reached a natural turning point. We’d shared what we knew, articulated our thinking, laid out a clear vision. But to move forward, we didn’t need agreement. We needed interrogation, offered with curiosity and care.

We needed people to ask us great questions. Not to catch us out, but to draw out the most interesting parts of the work. To name the patterns we could sense but hadn’t yet found words for.

That experience reminded me that knowing how to ask a great question matters just as much as knowing when to invite them.

And underneath both of those things is the same foundation: listening.

A question may open the door. But it’s your ability to hold the space afterward, to stay present, to retain the nuance of what’s shared, that makes the exchange worth having.