Don’t Solve Their Problem. Ask a Question Instead.

Great questions, good questions, dumb questions — any question is more useful than your opinion.

James Ryan Leonard
The Startup
Published in
8 min readMay 27, 2019

Leader, boss, parent, mentor, friend — as we embody each of these roles, we are consistently looked to for advice. They come to us when they aren’t sure what to do next. They bring us their intractable problems, looking for solutions.

And let’s be honest — it feels pretty good to be needed like this. And it feels good to solve problems for others, especially those who are close to us. But in almost every instance, the best and most helpful thing you can do is the opposite.

Don’t solve their problem. Ask a question instead.

This can feel counterintuitive at first, and it’s especially challenging when you’re feeling overwhelmed with life and work and you just need to get this person situated so you can move on to other things.

But when it comes to leadership and coaching (and parenting, and being a good person), one of the laziest and most counterproductive things you can do is try to solve someone else’s problem.

Instead, try to ask a question that allows the person to explore different courses of action for themselves. Ask a question that makes them rethink where their true challenge lies, or how they are prioritizing things. Ask what they are hoping to achieve, to help them focus on the path toward that end.

Asking great questions helps you avoid putting misplaced energy into solving the wrong problems, and it can lead to unexpected and elegant solutions.

The mantra of positive intent

The foundation of positive intent is a mantra of two core questions:

How can I help?

What can I learn?

In every difficult situation, with any challenge that arises, ask yourself, “How can I help?” Try to find some way to make the situation better or move things forward.

Failing that, stay curious. Ask yourself, “What can I learn?” Try to learn something about the other…



James Ryan Leonard
The Startup

Human, author, leader. Inward explorer. Ever a work in progress.