The Real Truth: How to Ask Great Questions

By October 10, 2019 May 27th, 2023 Self Management Tips

Last Updated on May 27, 2023 by Dave Schoenbeck

Can we influence others by merely learning to ask great questions? 

Think about the last conversation you had. Did the person ask you anything about yourself? How did that feel? Humans typically enjoy having the chance to talk about themselves, so chances are this made you feel closer to the question-asker. Did you ask them anything in return? 

The Real Truth How to Ask Great Questions

I have found that honest people will give you much more information when you ask great questions and get involved in their lives. You get an insight. You understand their purpose and passions. You become a brilliant conversationalist. Of course, patience takes practice and the ability to look past the timing of your next appointment, but it’s a worthwhile skill to have. 

The Power of Asking Questions

What made Dwight D. Eisenhower such an inspirational leader? In his book Dwight D. Eisenhower on Leadership, Phillip Schoenberg recounts this story as told by former speechwriter James Humes:

One day during WWII, a woman had lunch with Gen. Douglas MacArthur, Pacific Commander of U.S. Forces, and dined later that evening with Eisenhower. When asked about the difference between the two commanders, she replied, “When I had lunch with MacArthur, I learned how great he was. When I had supper with Eisenhower, I learned how great I was.”

What secret led to such a drastic difference between the two men? The answer is that Eisenhower knew how to ask great questions that made his audience feel valued. The natural result is a productive, free-flowing conversation that is mutually beneficial for all sides. So it’s understandable why this could be a valuable skill for a business leader

How to Ask Good Questions in Conversation

The quickest way to become better at asking great questions is first to become better at listening. Think about it: a conversation is a two-way street. Great conversation flows when two people take turns talking and listening. How can you ask a meaningful follow-up question if you don’t listen to what someone is saying?

When conversing, focus on what the other person is telling you. Don’t worry about coming up with what you will say next, as this distracts from the conversation. Instead, make eye contact and picture what it is they’re saying. Work on staying in the moment. When you accidentally tune out the entire message, asking great questions is hard. 

Next, be curious about the person you’re talking to. What do you genuinely want to know about what they’ve just told you? Questions asked from genuine curiosity carry much more impact than those asked only to continue the conversation. What needs clarification or intrigues you enough to ask for more information? 

Finally, as tempting as it can be, never interrupt while a person is talking. Even if a great question pops up, interrupting makes your conversation partner feel their words aren’t valued. Save your questions for when they’re finished speaking. This skill will carry you forward in business and life.

Learning to ask great questions can help you bond with your employees and lead to more productive conversations. Click here to fill out my contact form to learn how you can ask great questions and drive performance from your team.


Coach Dave


Dave Schoenbeck
Follow Dave