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How to Have Tough Conversations with Celeste Headlee (ep. 442)

Celeste Headlee

John O’Leary welcomes award-winning journalist Celeste Headlee to the Live Inspired Podcast.

Celeste Headlee is an award-winning journalist who has appeared on PBS, the BBC and NPR’s Tell Me MoreTalk of the Nation, and All Things Considered. With over 25 years of on-air radio experience, Celeste has a unique perspective on what makes for a good conversation.

Today, Celeste joins us to illuminate the path forward in having conversations (even difficult ones!) that actually matter.

In a time when there seems to be an abundance of talking at rather than talking with, today’s conversation is captivating, engaging and worthwhile, and emphasizes the importance of having real conversations with people on all sides of every equation.

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  • Celeste’s grandfather was William Grant Still, a composer, instrumentalist, arranger with a career that spanned decades, marked with “firsts” for a black man.
  • “One of the best things my family gave me was being role models without putting pressure to exceed their achievements.”
  • Celeste took a liking to opera because she was able to communicate using the power of her voice.
  • “To be a good conversationalist, you have to be as good at talking as you are at listening.”
  • Watch Celeste’s wildly popular Ted Talk 10 Ways to Have a Better Conversation here.
  • “We are losing connection with one another. We are seeing the hatred and the partisanship we’ve lost connection with families we’ve cut off friendship we know that something is going wrong and I think people are trying to figure out how to make it better.”
  • Celeste encourages each of us to say “I don’t know” when you don’t know.
  • “Our insistence that we know more than we do is dangerous. It has real-world effects you have to break through it by forcing people to explain their thinking.”
  • A self-described “light-skinned Black Jew,” Celeste has been forced to speak about race—including having to defend or define her own—since childhood.
  • Addressing race: Accept your bias and understand you’re going to make mistakes.
  • Get a copy of Celeste Headlee’s book Speaking of Race here.
  • Learn more about Celeste Headlee here.


Did you enjoy today’s episode? Film producer Tarek Mounib shares how to foster sincere dialogue and better understand people with viewpoints different than your own. His tips were learned on his journey with an unlikely group of U.S. travelers to the Middle East, captured in his film Free Trip to Egypt. Listen to Tarek Mounib on Live Inspired Podcast ep. 186.


About our sponsor: Keeley Companies wholeheartedly believes that if you get the people right -the results will follow. They set themselves apart with a forward-thinking culture that empowers their people and fosters loyal partnerships. Keeley Companies are a proud sponsor, partner, and super fan of the Live Inspired Podcast. Learn more about Keeley Companies.



  1. Q. What is the best book you’ve ever read?
    A. A Voice from the South by Anna J. Cooper.
  2. Q. What is a characteristic or trait that you possessed as a child that you wish you still exhibited today?
    A. I wish I did frivolous stuff more.
  3. Q. Your house is on fire, all living things and people are out. You have the opportunity to run in and grab one item. What would it be?
    A. A scrapbook of my son's first years of life.
  4. Q. You are sitting on a bench overlooking a gorgeous beach. You have the opportunity to have a long conversation with anyone living or dead. Who would it be?
    A. Ida B. Wells.
  5. Q. What is the best advice you’ve ever received?
    A. When I was frustrated with the lack of black and indigenous people history, my highschool AP teacher told me if I didn't like it to write a new textbook. Don't complain about it. Go change it.
  6. Q. What advice would you give your 20-year-old self?
    A. Stop dieting. You're fine and beautiful.
  7. Q. It’s been said that all great people can have their lives summed up in one sentence. How do you want yours to read?
    A. She did the best she could with what she had.