The best question I was ever taught to ask — While Daring Greatly

Adam Walker
2 min readAug 23, 2016
Photo by Camylla Battani on Unsplash

Years ago, I met someone that has become a good friend and mentor. We talked in the context of a small group, getting to know one another, and I noticed that Greg would often ask a simple question. He would say, “what do you mean by that?”

For example, in that setting with Greg, I might have said, “I want to be more productive,” and he would have quickly responded, “what do you mean by that?” to better understand my concept of productivity. Then I might explain my detailed plans for rising early, reading, writing, etc. Being asked the question allowed me to provide context and clarity around a vague statement.

I started asking that question too and have learned a few things from it.

People usually start with a vague statement about what they believe and will let it stand if left unchallenged. I don’t think people intentionally withhold the whole story. They summarize a thought or belief quickly, which has the appearance of being a complete thought but is much vaguer than you might realize. If asked, a person will often elaborate and give much-needed context to a statement to help you fully understand what they are saying.

The biggest thing that I have learned is how little I understand someone based on their first response.

I have a tendency to assume I understand a person quickly. This is a terrible habit if I am seeking to understand someone’s point of view. Instead, I have to fight the tendency to assume and force myself to ask, “what do you mean by that?” I am rarely disappointed with the answer. Usually, my knowledge of the person’s point of view gets much more profound. My understanding of that person, in general, gets deeper. And, my ability to empathize and connect with that person improves. In short, this simple question helps me make sure that authentic and meaningful communication is taking place.

The next time you are in an argument, discovering a client’s need, or talking to someone in simple conversation, and they make a statement about something they believe, don’t let the statement stand. Dig a little deeper. Ask them, “what do you mean by that?” You may be surprised at the response.

Originally published at on August 23, 2016.

Adam Walker

Husband. Father of six. Wearer of fedoras. Serial entrepreneur. Nonprofit co-founder. I write about personal growth & leadership.