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How to Have a Conversation That Matters | Celeste Headlee

How to Have a Conversation That Matters | Celeste Headlee

As a society, we’re more divided than ever. We don’t listen to each other long enough to find common ground. To have a meaningful conversation, your listening skills need to be just as good as your talking skills.


Celeste Headlee knows how to have a conversation that matters.

As a journalist and author of We Need To Talk: How To Have Conversations That Matter, Celeste is constantly looking for ways to improve as a conversationalist. And then, she tries to pass on what she’s learned to others. In fact, her TEDx Talk, 10 Ways to Have a Better Conversation, has over 26 millions views. Which is a testament to how thoughtful she is as a communicator- and how desperately we’re all trying to improve our conversation skills.

In a public radio career that has spanned over 20 years, Celeste has worked with several different media companies and people with a wide variety of views. She is also the president and CEO of Headway DEI, a non-profit that works to bring racial justice and equity to journalism and media through targeted training and interventions. She is the granddaughter of composer William Grant Still, known as the Dean of Black American Composers and she is a trained operatic soprano. And as an interviewer, she is someone I admire and look up to.

When I first started this podcast,

I was a newbie interviewer. And oh man, have I learned a lot over the last couple years. When you’re talking to someone you don’t know very well, and you’re trying to figure out what makes them tick, it can be exciting. And in that excitement, it’s easy to forget that you need to shut up and listen in order to come up with meaningful questions to drive the conversation. Celeste touches on this quite a bit, and gives tips on improving as a conversationalist. Because as she says, being a good conversationalist is about listening just as much as it is about talking.

We also get into the divisive political climate that tends to hang heavy in most conversations we have today. Believe it or not, guys, you can have a meaningful conversation with someone that has different political beliefs than you! In fact, Celeste believes most of the problems we have with communicating today, comes from letting politics cloud our humanity. You can be both right and wrong at the same time. And it’s easy to find common ground if you set aside your pride and just listen. This conversation about having better conversations was one of my favorites. Celeste opened my eyes to so many things I can incorporate into my everyday conversations with colleagues, friends, family and podcast guests. If you want to learn how to have a conversation that matters, check out my conversation with Celeste.


[00:07:09] The current state of communication

[00:09:37] How to have a meaningful conversation

[00:13:50] Why write a book on good conversations?

[00:15:47] Examples of healthy discourse

[00:27:42] You can be right and wrong at the same time

[00:33:33] Rules of communication

[00:42:18] The future of conversations


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