Ask One Good Question in Every Conversation

“Nothing shapes our lives so much as the questions we ask, refuse to ask, or never dream of asking.”

Sam Keen

“Ask me anything about myself,” said our guest speaker, who sat in a pinstripe suit at the head of the conference room table. One of my colleagues muttered, “Do you like your job?” The speaker nodded his head, “Yes,” and then turned back to the rest of the group. “Can you tell me about your experiences with policymakers,” said another colleague. “Yes,” answered the speaker brusquely. Everyone laughed. “Is your firm currently hiring?” inquired someone else. “No,” the speaker responded without taking a breath, and continued to scan the room for questioners.

Then, from the back of the table a soft-spoken young woman leaned in: “What’s an important lesson that you’ve learned in the last year?” “Ah,” said the speaker, “I’m so glad you asked. Let me tell you a story about what happened just last month when I was on my way to city hall…” Five minutes later, we were still sitting there enthralled, wanting to hear more about all the twists and turns that led the speaker to a profound truth.

This is a little exercise I often run in classes. Based on a program I participated in some decades ago, the speaker used it to show a group of us how much questions matter. More important, just how much the form of our questions matter. It was a simple illustration of the difference between closed-ended questions that elicit yes/no responses and open-ended ones that tend to steer conversations in more expansive directions. The speaker illustrated in real-time that the types of questions we ask play a large part in the scope of what we end up knowing. There’s an art and science to question asking, such as making how and what questions a foundational skill in connecting with others.   

Across a number of books, Neil Postman once lamented how many school and other curricula prioritize answer-giving over question-asking. If research / questions are the source of everything that we know (or think we know), every topic or endeavor should make good inquiry its starting point. For instance, science teachers have found that opening classes with a mysterious question (such as “What are Saturn’s rings made of”?) and telling stories about scientists’ attempts to answer them will keep students guessing and engaged right through to the end of every class.

This all goes deeper than just using questions as a tool. Every person’s identity and outlook are the result of the questions they have or haven’t asked. While it’s sound advice to “live the questions,” we also live the questions not asked. In the last several years, I’ve noticed that for many people avoiding questions about politics has become an achievement. Whether it’s a statement about environmental degradation, tax policy, or geopolitical events, it’s rare to hear someone say, “what don’t I know about this topic” or “what more do I need to learn about that?” Starting with the question—and bringing honesty along for the ride—might do more to quell local or global conflicts than any other measure. A little less certainty or overstatement from all sides would go a long way, and that all begins with questions.

So, here’s two worthy challenges to get us all practicing the skill of asking questions. First, open a conversation with someone this week and see how long you can keep it going by asking questions. (Credit to the marvelous Greg Spencer for this prompt). Second, try your hardest to ask at least one good question in every conversation. I think that you’ll find there’s worlds opened, adventures awakened, and new connections made with each good question asked.