How to Have a Meaningful Conversation

Lately, I’ve been thinking about what makes a conversation truly meaningful. Then I stumbled across a TED Talk called “10 Ways to Have a Better Conversation” by Celeste Headlee, and it pretty much summed up everything I’ve been feeling. I’ll drop the link at the end if you want to check it out—maybe you’ll want to skip my take and just watch that. But here’s my version anyway.

I’ve always loved a good conversation. Sometimes I walk away feeling energized, curious, and connected. Other times, not so much. Listening to Celeste helped me understand why that is. These are some of the key things I picked up from her, mixed in with my own take.

First Things First: It Takes Two

Good conversation is part communication, part listening. Both matter. There are a lot of myths out there like: “Make eye contact,” “Have interesting topics,” “Nod a lot,” “Repeat back what they said”—but honestly, none of that matters if you’re not actually present. Ever talk to someone who’s nodding but clearly not there? Yeah. That’s what I mean.

The best conversations make time disappear. I lose myself in them and often don’t want them to end. That’s the kind of interaction I’m always on the lookout for.

Get in the Right Space First

Before I dive into a conversation, I check in with myself. Do I have the energy or time for this right now? If not, I’ll be upfront—maybe we can just say a few words and come back to it later. And if it’s something I’ve planned ahead for, I might prep a bit—have a few topics or questions ready. Not always necessary, but it takes the pressure off if I’m not feeling especially “on.”

Celeste’s 10 Tips for Better Conversations (With My Spin)

1. Kill distractions.
Put the phone away. Turn off the TV or music. Stop multitasking. If you want to be in the conversation, be in it.

2. Don’t pontificate.
If you just want to talk without being challenged, write a blog or give a speech. A conversation is a two-way street. As Bill Nye said, “Everyone you ever meet knows something you don’t.” Show up ready to learn.

3. Ask open-ended questions.
Who, what, where, why, how? Simple questions lead to richer answers. Be curious. Go easy. It helps others open up.

4. Go with the flow.
This one hit me hard. When a thought comes up while you’re listening—let it float on by. Don’t latch onto it and start planning your response. That’s when you stop listening and start talking to yourself. Let. It. Go.

5. Be honest.
Don’t pretend to know stuff you don’t. Drop the act. Being real creates real connection.

6. Don’t compare your experience to theirs.
You and I could both have a crappy day—but those two days are nothing alike. Just be there for the other person. Don’t hijack the story.

7. Don’t repeat yourself.
Guilty as charged. I’m working on it. Once is enough—twice is too much.

8. Stay out of the weeds.
No one cares about names, dates, or tiny details. Conversations are for connection, not information dumps. Keep it simple.

9. Listen.
The hardest one of all. Most of us don’t listen because we’d rather talk—it’s easier, we’re in control, and we don’t have to face stuff we might disagree with. But real listening takes energy and attention. Without it, you’re not having a conversation—you’re just talking at someone.

10. Be brief.
Short and sweet has more impact. I don’t want a lecture—I want connection. Get to the point.

So next time you’re in a conversation, really hear the other person. Be ready to be surprised by what you discover—and maybe even changed. Good conversation isn’t just fun—it’s a path to friendship, understanding, and going deeper with the people around us.

Cheers,
Chris

Here’s the TED Talk I mentioned:
▶️ Celeste Headlee – 10 Ways to Have a Better Conversation