Celeste Headlee’s 10 Ways to Have a Better Conversation

A clue: it's not about you!



Conversing, networking and building rapport is at the core of both business and life success: being able to converse freely, confidently and, in most cases, briefly, signals to those around you that you’re clever, in control and self-assured. And, most importantly, that you care about other people.

Writer and radio host Celeste Headlee argues that due to the increasing use of ‘within reach’ technology, we’re losing our ability to converse face-to-face and that opens a whole other can of worms for modern conversation. We often use conversation as a platform for our own thoughts and feelings, rather than a place of discussion and understanding.

Here are her 10 rules to having a better conversation.



The most fundamental concept of all good conversations (and life in general) is the ability to listen. It’s the hardest thing to do but it’s the most important.

“When I’m talking, I’m in control. I don’t have to hear anything I’m not interested in. I’m the centre of attention. I can bolster my own identity,” Celeste says of our obsession with talking instead of listening.

“Buddha said, and I’m paraphrasing, ‘If your mouth is open, you’re not learning.’”

You are listening to understand, not just reply, and it’s something that’s often, but should never be forgotten.



We all know that doing something else, anything else, while someone is trying to have a conversation with us can be infuriating: think of how you feel when someone is scrolling mindlessly while you try and tell them about your day. But Celeste says it’s more than just giving them your attention.

“Be present. Be in that moment,” Celeste explains. “Don’t think about your argument you had with your boss. Don’t think about what you’re going to have for dinner. If you want to get out of the conversation, get out of the conversation but don’t be half in it and half out of it.”



A classic mistake that anyone on the receiving end despises. Does anyone want to be preached to without the possibility of coming to a healthy mid-point of ideas?

You’re not having a conversation if you’re just talking at someone.

“If you want to state your opinion without any opportunity for response or argument or pushback or growth, write a blog,” Celeste agrees. “You need to enter every conversation assuming that you have something to learn… sometimes that means setting aside your personal opinion.”



“If you put in a complicated question, you’re going to get a simple answer out,” Celeste explains. “Let them describe it. They’re the ones that know. Try asking them things like, ‘What was that like?’ ‘How did that feel?’ Because then they might have to stop for a moment and think about it, and you’re going to get a much more interesting response.”



Almost everyone is guilty of this speaking sin: someone will be talking, you’ll come up with a great idea or story and interject or, in some cases, wait impatiently until the person finishes the sentence and jump in.

“We’re sitting there having a conversation with someone, and then we remember that time that we met Hugh Jackman in a coffee shop. And we stop listening,” she says. “Thoughts will come into your mind and you need to let them go out of your mind.”

Interjection is fine – if it helps reinforce a point for the person talking, if it’s short and it doesn’t derail the thought process of the speaker but don’t forget to give someone else the space to tell a story. That’s called listening.



There’s nothing worse than being caught out in a lie and admitting that you don’t know something doesn’t make you look dumb – it makes you look honest. As the old adage goes, honesty is always the best policy and it should always be that way for conversations.

“Err on the side of caution,” says Celeste. “Talk should not be cheap.”


We may have gone through similar things to our colleagues or friends but as different as we are as people, that’s how different things can affect us.

“If they’re talking about the trouble they’re having at work, don’t tell them about how much you hate your job,” Celeste says. “It’s not the same. It is never the same. All experiences are individual. And more importantly, it is not about you. Conversations are not a promotional opportunity.”



Put simply: it’s boring. And it makes your listener feels as though you’re self-centred enough to forget that you’ve told them before. Many times.

“Especially in work conversations or in conversations with our kids, we have a point to make, so we just keep rephrasing it over and over,” Celeste points out.



“Frankly, people don’t care about the years, the names, the dates, all those details that you’re struggling to come up with in your mind,” Celeste says. “They don’t care. What they care about is you.”

Peppering your conversation  with details is fine but only if it benefits your listener, not your own peace of mind.


10. “BE BRIEF”

This one speaks for itself. No one likes people who tie others up in conversational knots for hours. We don’t like being talked at, or made to feel as though we could be anyone, just being a silent ear.

Celeste quotes her sister on the subject: ‘A good conversation is like a miniskirt; short enough to retain interest, but long enough to cover the subject.’