How to have more meaningful conversations

In the last two nights, I’ve experienced two of the best conversations and dining experiences since moving to Boulder.

Nothing about the actual meals or locations was that unique. I’ve known both people well and we’ve exchanged a number of worthwhile interactions. But something felt very different this time. There was a newfound presence and connection. And we both left feeling like it was one of the most interesting conversations we’d had in a while.

So what was different?

I came prepared with three questions that I felt would cultivate a meaningful dialogue.

I’ve come to recognize that if I don’t feel present in a conversation, it’s because I’m bored. And I become bored when I’m not learning. Talking about what we did in our days and what we’re doing this week can only hold my attention for so long—and it’s not very long at all.

Now, each week, I’m making an effort to create three questions that I’m interested in exploring. In the one-on-one conversations I have that week, I’ll bring the questions up. This way, every interaction becomes an opportunity for learning, growth, and more depth in the relationship. It’s also a fast way to build a more well-rounded perspective on any topic of interest.

Here are my three questions of interest for this week:

1) What’s the difference between like, love, in love, and lust?

2) What are you certain of?

3) How do you listen to your inner voice?

I’ll have more on what I’ve learned from these questions in future posts.

In the meantime, I encourage you to come up with your own three questions. Whether with someone you know well or a complete stranger, use these questions as a way to provoke meaningful dialogue in your conversations this week. The learnings might surprise you!

(Update: Intent is key. The aim shouldn’t be to control the conversation. It should be to connect more deeply and learn more about the other person. I’ve found that not everyone is willing to go deep and be vulnerable so it’s situational and I feel it out as I go.

Also, my friend Kevin suggested a new iteration of Eleanor Roosevelt’s quote, which I love and feel captures the intent of this post: Small minds discuss mere ideas, average minds discuss how those ideas might change the world via events, and great minds may discuss people’s souls.)

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Thanks to Nathaniel, Teju, and Eric for inspiring this post and Ryan and Vivek for reading the draft.