How to Have Good Conversations

Red Calayan

September 13, 2019

What makes for a good conversation?

We all know the feeling of meeting someone for the first time and being delightfully surprised that you actually had a really good conversation. We also know what the opposite feels like, when you talk to someone for the first time and after a few lines, the conversation just died.

This happened to me one time during a big event.

I was at a big party celebrating the success of this one project. This friendly guy dances up to me and my friends to help welcome us, and he shouts to us over the loud music, “Yo, isn’t this a great party?” And we say, “Yeah, it is!” And then nobody said anything for 10 seconds, and then he just says, “Alright!” and dances away. In just two lines, the conversation died, and we never spoke with him again.

So why did that turn out to be a bad conversation? But maybe we should actually ask, What makes for a good conversation in the first place? Asking this is like asking what makes for good music or good art—you know what it is for you, but it’s hard to describe unless you really study it and take time to think about it.

Upon reflecting on hundreds of past conversations both with people I’ve just met and people I’m already friends with, I came to the conclusion that a good conversation is this: When two people connect in a way that flows naturally, creating or reinforcing friendship and the desire for more conversations.

Good conversations don’t just create good moments; they help connect people and form friendships.

So how can we have good conversations?

It boils down to three questions: Who is it about? What are you trying to do? And what’s your posture?

It’s not about you.

Great conversations happen when your attitude is that this conversation is not about me—it’s about the other person.

A key truth we find in human interactions is that people love to talk about themselves. People love being able to express who they are, what they’re about, what their passions are, and so on. If you give them that chance, you’re already winning a new friend.

Try to find something they’re passionate about and let them geek out about it. I remember becoming friends with an Angkas driver just because I let him geek out about motorcycles. I didn’t understand half of what he said because of the wind, the helmet, and the traffic, but by the end of the ride, he was grateful for the conversation.

Taking the focus off yourself and focusing on the other person also makes you less self-conscious. If we focus on ourselves, we’ll be too preoccupied with thoughts of how we look, what kind of impression we’re making, whether the other person thinks we’re cool, and the like. But when we take the focus off ourselves and consider the other person more—gauging how they’re feeling, if they feel welcome, if they feel at ease, if they are having a good time, how can we serve them more—then conversations will flow more and we can approach people with more confidence and less apprehensions.

So how do we do this? We must become sincerely interested in the other person and the things they’re sharing. Whether they’re sharing about their passions or just things they really care about, we must be interested in knowing them and knowing about their lives. We have to give our full attention, so phones down and stop yourself from checking the time. Be quick to listen and slow to speak. If you accidentally interrupt the person, then just apologize and let them speak. This has a huge effect on conversations, and it tells people that you really want to listen to them. Ask follow up questions about what they’re sharing. Show them that you really want to know more.

Don’t just gather information. Find points of connection.

One of the best feelings in the world is when you share something in a conversation and the other person absolutely gets it. When the other person’s reaction is, “Hey, I know what that’s like!” there’s just this feeling of, “Wow, I’m understood. Someone gets me.”

If you can let the person you’re talking to feel that you understand them, that you can relate to them, and that you do actually share some common ground, then you’re on your way to making a new friend.

For example, if they share a certain kind of experience—a hassle they experienced in school, an embarrassing moment, or a good experience—feel free to share your own to show them that you can relate.

People connect when they realize that they have shared interests, experiences, frustrations, likes, dislikes, or even annoyances. Sometimes, the easiest way to break the ice is through a common complaint. For example, it’s really easy for me to strike a conversation with a taxi driver if I say grabe ‘yung traffic, or ‘yung ulan, or ‘yung init. And we get to laugh about it and start a conversation. Lighthearted complaints that express the shared human experience and create connections are, to me, forgivable and effective. [Remember not to dwell on the negative experience though!]

Make sure you use these points of connection to establish common ground and not to brag about the knowledge or experience you have with the topic. There’s a fine line between those two intentions and people can tell when you’re just trying to look smart.

And don’t make up points of connection. If you can’t relate to something, just be upfront about it. For example, you could never force me to talk about the NBA because I know nothing about it. If you do, I’ll start talking about how many touchdowns Michael Phelps made against Manchester United.

Watch your posture.

People can tense up or relax depending on the posture of the person speaking to them. If you approach someone and try to befriend them but you have the posture of trying to prove who’s better, who’s more cool, or who’s the boss, you’ll end up intimidating people and turning them off.

Instead, take up the posture of a good host at a party. You own the place and everyone else is a guest, so you’re not going to be shy to speak to people, but you’re also not going to be arrogant and intimidating, because your job is to make sure people feel welcome and at home. Be friendly and humble and show genuine care. Bring out the best in people and make them feel good about themselves.

Learning to have great conversations will take time. I guess it can really be compared to good music or good art—because it is an art rather than a set formula that you can simply take and apply. It takes practice to get better.

It will take a lot of effort, but at least you’ll have a great party where conversations don’t die after two lines and people don’t have to dance away in awkwardness.


The Author

Red Calayan

Red Calayan is a full-time LIFE coach at Every Nation Campus Katipunan. He is also a former radio DJ, professional meme creator, sitcom script writer, and drummer (or "drummer emeritus" as his bandmates like to say) of a local band, Munimuni.