Wait, What?: A Thought-Provoking Guide To Asking The Right Questions

by James E. Ryan

Asking good questions is hard because it requires you to see past the easy answers and to focus instead on the difficult, the tricky, the mysterious, the awkward, and sometimes the painful.

In almost every instance, it is better to ask clarifying questions first and to argue second. Before you advocate for a position, be sure to ask “Wait, what?” Inquiry, in other words, should always precede advocacy.

For whatever reason, most people, I have noticed, tend to become less curious about the world as they age. It may be that their curiosity was not sufficiently encouraged by parents or teachers, who can become weary of the “why” question. The logistics of life can also crowd out curiosity, as simply getting through the day presents its own challenges for adults. Regardless of the reason, it is the exceptional adult who has retained a child’s innate curiosity about the world around her.

sometimes the most important decision you can make is the decision to get started. One of my favorite quotes, sometimes attributed to the German writer Goethe, is this: “Whatever you can do or dream you can, begin it. Boldness has genius, power, and magic in it.”

Getting started does not guarantee success, but it does guarantee that you will not live with regret about failing to try,

If you ask others how you can help, you are inviting them to take some ownership of their own problems. For this reason, it is a useful question to ask friends, family, and colleagues. It is a particularly useful question, I have found, to ask kids and young adults.

you alone need to decide what truly matters about your work, your family, your friendships, and how to be kind. And you need to decide how to balance those values when they are in tension or in full-blown conflict, like the ever-present need to balance work and family.

get beyond simply identifying the categories or topics that matter to you and to think through what is going well, what could go better, and why.

“Wait, what?” is at the root of all understanding. “I wonder . . . ?” is at the heart of all curiosity. “Couldn’t we at least . . . ?” is the beginning of all progress. “How can I help?” is at the base of all good relationships. And “What truly matters?” helps get you to the heart of life.