The Secret to Asking Great Questions

Earlier this summer, one of the leaders I’m developing said, “You seem to ask really insightful questions. How do you do it?”

The Secret to Asking Great Questions

Perhaps some of this is easier for me because I am curious by nature and can think on my feet fairly well, but you can learn to ask great questions. Here’s the secret:

Genuinely care about the person you’re talking to.

When you care, you listen.
When you care, you notice details.
When you care, you work to understand.

Don’t think about what you’re going to say next.
Don’t relate everything back to you.
Don’t look for opportunties to trump their story (you “Me Monster”).

And care genuinely. Not out of duty. Not to manipulate. We smell that a mile away.

Care because you really care. (You could call this “love”)


How can a leader cultivate genuine care when, honestly, he or she don’t really care about a particular person?

(HT: Image Credit)

Published by Luke Simmons

I was born and raised in Denver, CO and lived there through high school. Then I moved to Champaign, IL where I attended the University of Illinois and played on the Fighting Illini baseball team. I was married in December, 2001 to Molly, who I met at the U of I. In June of 2002, we moved to Phoenix and have been here ever since.

5 thoughts on “The Secret to Asking Great Questions

  1. Well, the answer would be to look to Jesus and the example of the Gospel. If He could love me when I was still an enemy of God, I guess I can try to show love to someone I think is annoying or don’t care for.

    1. What are some tips for sharing similar experiences for the purpose of relating and showing empathy without coming across as “trumping” or trying to relate things back to you?

  2. I’ve been convicted over and over again recently that I judge people, primarily on appearance, and therefore I miss out tremendously on what that person or group has to teach me. I won’t tell the long story, but the short story is that I’ve been challenged to remind myself, “You don’t know their story, do you, Howard?” It is helping me short-circuit my knee jerk reaction and sincerely take the time to listen to someone’s story, their journey. I have much to learn, if I’ll get over my arrogance, stop, and ask a few probing questions….then listen!

  3. I’ve found that investing time in prayer for people who I want to genuinely care about is very effective. I think we care about what we invest time in.

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