What Makes for a Better Conversation?

Estimated reading time: 3 minutes


I piloted a new event this week called Let’s Talk — a one-hour online session where people pair up for short conversations using thoughtful prompts.

At the end of event, I asked everyone a simple question:

“What makes for a better conversation?”

Three factors came up: connection, curiosity, and confidence. And they’re all connected (pun intended).

Note: the alliteration was completely serendipitous!

Connection

Connection can be as simple as sharing a preference (“I’m a night owl, too”), a hobby (“I rock climb, too!”), or an interest (“I also love K-pop!”).

What it really comes down to is realizing someone else sees the world a little like you do. That overlap makes conversation easier. It reminds you that you’re not as different from others as you sometimes think.

Connection doesn’t need to be big or deep. Think of it as connection with a little c — as simple as laughing at the same joke or ordering the same pastry.

Curiosity

Everyone says they’re curious, but it can be harder to show it — especially with people. It’s easy to be curious about how things work or who did what.

The kind of curiosity that matters for 1:1 conversations means shifting from talking about yourself or things to wanting to learn about the person across from you — their experiences, beliefs, feelings, and values.

Curiosity invites depth.

The best conversations often include questions that sound like:

“That’s interesting! What made you start doing that?”
“How did that feel?”
“What happened next?”

Confidence

I’ve written about confidence before, so hopefully you’re familiar by now!

Confidence is the willingness to talk about yourself, ask questions, and get out of your own head long enough to be curious about someone else.

The most memorable conversations aren’t about cleverness — they’re about something real.

Confidence lets you speak honestly, share your quirks, and let the other person actually meet you — not a polished version of you.

Bringing It Together

When you’re connected, curious, and confident, you create opportunities for better conversations (yes, even with a stranger on Zoom).

So, which one are you going to work on?

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Why Conversations Fizzle Right After Matching

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The Kindest Interpretation