The Gentle Art of Asking Questions

October 22, 2021
Wally Bock

During my last years in high school, my father was pastor of a parish in New York City. Because of the reputation of the parish and the location, we hosted many receptions.

The receptions drew all kinds of people. There were people affluent enough to live in the Upper East Side of New York. There were others who came after work in the nearby skyscrapers. Most fascinating of all, there were diplomats, mostly from UN delegations.

When you host a lot of people at social events, it’s good to have a way to recognize people and know something about them. My mother met that challenge with her 3×5 index cards. Each one had a person’s name and some notes about them. I don’t remember many of them, but I still remember one about a member of a UN delegation. It read:

“Strange mustache. Don’t stare!

Ask about tiger hunts.”

Those receptions were over 50 years ago. I still remember many conversations from them. It was where I learned about the power of asking questions.

You Can Learn A Lot Just by Listening

When you ask a question, the answer adds to your store of knowledge. The trick is that you must be quiet and listen. Mother reminded me often that you can’t learn while you’re talking. She taught me that it was rude to interrupt someone in the middle of their answer. She didn’t say anything about learning a lot, but I did.

The late Clay Christensen once said that a question is a place in the mind for an answer to light. A particular piece of knowledge means nothing to you until you ask a question. Then, the question gives it a place to go in your mind.

People Will Think Well of You When You Ask Questions

I was in my late teens then, and my sister was five years younger. We didn’t have the education or the experience or the worldliness of the people we spoke with. But because we asked questions and listened, people always complimented my mother on what great conversationalists we were.

People like to share their stories and their information. When you ask questions, you put the spotlight on them. The trick is to ask questions about things the other person is interested in. Then, you give them an opportunity to show off.

You Can Start a Conversation with a Question

When I was a teenager. I learned to ask questions and I learned to listen. Years later, I figured out that questions are a powerful leadership tool.

In my classes for new managers, I always stress touching base a lot and having conversations. One day, one of the people in the class asked me, “Okay, how do you do that? How do I start a conversation?”

I hadn’t really thought of it up to that time, but I’d been doing it for years. If you want to start a conversation with someone, the easiest way is to ask them a question. I’m not talking about a work-related question that can be answered with a number. I’m talking about something the other person is interested in and you would like to hear more about.

One of my early bosses started every visit to my office or every phone call with the question: “What’s interesting in your life right now?”

Use Questions to Control the Conversation

There are two basic kinds of questions: open-ended and closed-ended. Closed-ended questions can be answered with a simple yes or no or a fact or two.

If you start asking closed-ended questions, the give-and-take of a good conversation dries up. But if you use open-ended questions, the kind that need more than a yes or no, the conversation will flow.

The Gentle Art of Asking Questions

There are lots of ways to ask questions. There are times when you need a quick answer and not a conversation. But if you want to have good conversations where both parties benefit, you need to do a few things.

Ask about something you’re interested in. If possible, ask a question that the other person will enjoy answering. Then, be quiet and listen. Ask your question. Then stop talking.


Questions are the keys that unlock the chamber of knowledge.

People will think well of you when you ask good questions.

Questions are a great way to start a conversation.

Open-ended questions help conversations continue.

Closed-ended questions make conversation grind to a halt.

You get the most from your questions when you ask about something the other person is interested in and then listen.


Bob Tiede’s website Leading with Questions

The Coaching Habit: Say Less, Ask More & Change the Way You Lead Forever by Michael Bungay Stanier

More From Wally Bock

3 Things Effective Leaders Do

5 Things You Can Do to Be a Better Boss

Leadership: Over the Hills and Far Away

In addition to writing the Three Star Leadership blog, Wally Bock is an author, ghostwriter, writing coach and book doctor. In his past lives he has run a small publishing company, been a popular keynote speaker to audiences around the world, and served as a U. S. Marine. He loves good beer, good friends, and good stories.

Photo by Christina @ on Unsplash

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