3 Questions to Help You Make Great Conversation

My girlfriend told me a guy at work said she was a great conversationalist.

And then she said, “I really didn’t say anything. All I did was ask questions about his baby and listen to him talk”

I think that’s all a good conversation requires.

Making great conversation isn’t about talking, it’s about making people feel heard. It’s about asking great questions and actively listening.

But when we first meet someone, we can get anxious about what to say. So here are three questions that help me have deep conversations.

1. What was the best / worst part of your week?

In 2020, I made it my New Year's Resolution not to ask people “how are you?”. Everybody asks that and usually we get the same response. I tend to say "fine" out of habit even when things are NOT FINE.

This question takes some thought. It digs into what people are excited about or struggling with right now. And for those of us who struggle with talking about our lives, it gives us a built-in opportunity.

2. Out of anything you could be doing, why do you choose your career / major?

I'm fascinated with why people do what they do. Not only does it give a window into their story, but it can tell you about someone’s interests, aspirations, dislikes — the list goes on.

I know career or major can be driven by circumstance, but I find that people usually have choices – even if they're limited.

Pro Tip: I often turn this into a game. When I first meet someone, I ask them to tell me why they chose their career and then I try to guess it. Trust me, it’s fun.

3. Which one of your parents are you more like? Why?

As I grow up, I become painfully aware of how much I’m like my parents. I love this question because it helps you get to know where people come from.

Let’s face it, we inherited both good qualities and bad from our parents. Talking about our parents can be an easier way of talking about ourselves.

If done well, this can be a deep conversation starter. Or maybe a therapy session.

Making Conversation Isn’t About You

We don’t have to have the best stories or funniest jokes to make conversation.

Because it’s not about us.

Making great conversation is primarily about making other people feel heard. And hopefully, the other person will do the same for us.

So, try out one of these deep conversation questions. Let me know how it goes in the comments!