How to become a good question asker

How do you become a good question asker?

Here’s a text exchange I had earlier this week:

Friend: Hey brother, question for you. You ask phenomenal questions - how did you hone that art / improve your listening? Any books you’d recommend?

Me: Hey bud - Thanks for saying that. Happy to help.

Most important thing is the one question I ask before being with people. What do I most want to learn about the person(s) I’m about to meet.

Has become more of a practice of cultivating curiosity than building an arsenal of questions.

That said, I love a good question. Andrew Sobel is my favorite for business. School of Life is best for personal/social.

Friend: Love this. What if you are just meeting someone socially who you didn’t plan to meet, how do you create that curiosity?

Me: Great question, my answer is to do an exercise that articulates your intrinsic curiosity for people. It’s simple, ask yourself the question, “what am I most interested to understand about people?” Then, make a list of the questions that do justice to your curiosity. I often call this the big 5 or big 10. When you write them down, you are more likely to bring them up naturally In conversation. I like to think of this as honoring our curiosity.

For example, here are my Big 5 right now - 1. What are you Most excited about? 2. What’s challenging right now? 3. What have you learned recently? 4. What do you care about right now / what are your priorities? 5. What’s your dream?

For me, it’s never about remembering these in conversation, where it would feel scripted. I just bring awareness to them by writing them down and make them more available should I want to know these things about whoever I am with... more often than not, I do and I’ll naturally flow into them.

What are your favorite questions to ask new people? What’s your Big 5?