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  • Writer's pictureRyan Jones

My wife says I need to practice this one topic more.

In last Monday’s blog post, I talked about comparing for the purpose of learning. In today’s post, I want to elaborate a little on the art of asking questions. Now, I’m an introvert and asking questions tends to lead to longer conversations, which I’ve learned to love. Let’s be clear, this is not natural for me. I had to work hard to learn and develop this skill, and to develop the interest to stay connected longer. a skill I’m still working on today.


Here are some questions I’ve used to help me over the years:

  • What’s on your mind?

  • What’s a challenge you are facing today?

  • What’s one of your current goals? What is standing in your way?

  • What are three things going right for you?

  • What is something you are working on right now? What is your motivation? What’s your secret to staying focused?

  • Tell me more about...?

  • That’s fascinating. Tell me a challenge you had to overcome to achieve that.

  • Congratulations. I bet that wasn’t easy. What was your secret to success?

One other thing I learned in my EMBA class was the concept of double-click. The name is related to you trolling the internet and something with a link catches your eye, so you click. Then something more catches your eye, and you click again. This may or may not stop. Next thing you know, you’re caught in a fascinating web of learning. Try this in a conversation: listen for a word or phrase or object that catches your interest, then ask a follow-up question targeted at that "thing". See where the conversation takes you. Diving deeper, next thing you know you’ve had a fascinating conversation with someone, and the ending topic was by no means where the conversation started. The trick here is to listen to what the person is saying, not so you can jump in and say more of what you are thinking, but to carefully hear the words they are saying and double click into their conversation.


Let go of your conversation agenda. There will be enough time for you to share. Most people will at some point ask you a question.

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