How to Have an Interesting Conversation

Have you ever eavesdropped on random people at a cafe, on a subway, or at your office? If you have, let’s be honest, for the most part, you quickly find their conversations incredibly boring.

Is this because of data in their brain or because of the way to query the data? I can’t do anything with the former other than not talking to them, but for the latter, I have been trying to come up with interesting questions. I just can’t tolerate boring conversations. Plus, nobody wants to have a boring conversation. So why not thinking about good questions up front?

When you talk to strangers at parties, probably the most common question is, "what do you do?" Tragically most people don’t have the luxury of working on what they love as a job. Thus, it’s unlikely that you get an interesting answer.

“What interesting books did you read recently?“ will cause the majority of people who don’t read to be perplexed.

“What are you most excited about right now?“ sounds better. But it doesn’t seem to trigger interesting answers either. Most people, unfortunately, don’t have anything they are excited about. People are too busy working on something they are not excited about.

In my own research, the best question to ask people I don't know is, "What are you interested in?" First, this is open-ended. It can be anything like movies, sports, art, etc... Second, it’s easy to answer. Everybody has an interest in something. Thus, you won’t have any awkward moments. Their answer might or might not lead to interesting conversations but at least you increase the possibility. Empirically, this triggers more interesting answers than “what do you do?”. If you share interests with them, your conversation is going to be fun.

I try to come up with questions that lead to more interesting conversations depending on their interests. If they like gadgets, I might ask “What purchases had the biggest impact on your life recently?” Are they into programming? Then I might ask, “What is the favorite thing you’ve built?” They like art and design? I might ask, “Who do you admire as a designer/artist?” They seem to like self-improvement? Then ask “What is one of the best or most worthwhile investments(money, time, etc...) you’ve ever made?”

To enjoy the conversation, I listen actively and try to stay genuinely curious. I nod often and summarize what they say. If they talk about something I don’t understand, I don’t leave it. I tell them that I don’t understand and ask for an explanation. I ask for specific examples when the conversation gets too abstract.

If I could find out that a person likes to read, I jump to books. I casually ask, “Read anything interesting these days?” If I knew that this person is quite curious, I might ask “What are some books that have greatly influenced your life?” When she knows how to read books, it’s more likely that you can have an interesting conversation.

This is why I love people who read books. When I befriend them and meet a month later, I can simply ask what books they’ve read and discuss.

I try to come up with questions even when I meet friends. I even explicitly tell some friends that I’m going to list some interesting questions to ask before I meet them. If you were lucky enough to have curious friends, you will be surprised how much you can find out more about them. If you were hanging out with friends who know how to bring an interesting topic to a table, you could simply ask “What have you been thinking lately?”, “What’s something cool you’ve learned recently?”, etc...

I’ve decided to keep in mind that she who asks lead. If you want to have an interesting conversation, you gotta lead. You are responsible for making a person in front of you interesting. If you ask, “Where are you from?”, you effectively make him boring. Nobody is gonna be interesting with bad questions.

One caveat, though, is not to forget to humanize conversations. Don’t make people feel that a conversation is transactional. A conversation is more than just an exchange of information.

Let me know if you have good questions to ask.