8 Questions to Create an Interesting Conversation

I love questions that make conversations, life more interesting. After reading this article last week, I’ve been thinking a lot about questions I like that make for fascinating conversation. Here’s a short list:

  • What do you believe is true that almost nobody agrees with? (The Peter Thiel question)
  • What’s the last thing that made you laugh out loud?
  • If you could call yourself five years ago and had 30 seconds, what would you say?
  • Someone gets a text message from you, and for whatever reason they’re not sure it’s actually you. They’re worried that someone may have stolen your phone. What could they ask to make sure it’s really you?
  • If you could wake up tomorrow having gained any one quality or ability, what would it be?
  • What’s something about you that people are usually surprised to learn?
  • What’s something that’s exciting to you right now?

Related, check out questions you can use to get the most out of meetings.

Let me know of any questions you use in the comments below!

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  • Gary Wu

    Hey Justin, nice post. I think about questions that make for interesting convos as well. I’ve found a good line is, “What’s keeping you busy these days?” – open ended, and allows them to talk about anything be it work, personal life, hobbies, etc. You can then follow up by asking what their biggest challenge is in X, which allows you to potentially add value to them.