Break the Wheel: Question Best Practices, Hone Your Intuition, and Do Your Best Work

Your best work won’t be created by the answers others give you, but by the questions you ask yourself. So starting today, right now, do what others might consider unthinkable—not because you’re doing anything radical, but because in a world full of so much average work, you know what it takes to do something exceptional. Go break the wheel.

I’m not asking you to follow anyone else’s definition of what it means to be exceptional. I’m asking you to find your own. I’m asking you to think for yourself in this world overflowing with conventional thinking.

What matters isn’t that we stick to anyone’s framework, including mine. What matters is that we ask questions, foregoing the notion that anyone else has “the” answers for us. What matters is that we understand how to find our own, changing what we know as our context changes.

However, I wouldn’t be listening to my own message if I didn’t encourage you to find your own too. If these questions work for you, that’s great. If you substitute others or identify more, then that’s even better.

When we ask good confirmation questions, we ensure we’re on the right path toward our goals when we take action. That’s the entire point: turning better thinking into better action.

When we ask good trigger questions, we spark our curiosity and begin our investigation. We put a little distance between us and that ever-spinning wheel, creating some necessary cultural disfluency to begin thinking for ourselves.

Your goals, metrics, budget, headcount, timeline, and more—they all create a set of limitations, a sort of box within which you might actually be more creative. To do so, however, you need to understand the walls of that box.

No part of your situation is more vital to your success than your specific audience—whether that means your customers, prospects, readers, viewers, listeners, or even a boss or client you’re trying to help or persuade. For whom are you creating your work? Ask the right questions about them.

You The person or people doing the work. What is your aspirational anchor? Your intent for the future, combined with some hunger you have today, some dissatisfaction. Turn your vague desire to do exceptional work into something specific and concrete. Give yourself the first filter, through which you can vet best practices as possibilities—they serv