088: How to have better conversations – with Celeste Headlee

By October 22, 2019October 23rd, 2019The Simplifiers Podcast

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Do you get annoyed in conversations when it seems like the other person is just waiting for you to stop talking, so they can speak? Surely there is a better way!

My special guest today is author Celeste Headlee and she’s simplifying how to have better conversations. If you dread hearing these four words, “we need to talk,” this episode is especially for you. We tackle the lost art of conversations and why we feel less connected and more divided than ever before… How do we make it better? Celeste says, “the only way forward is to start talking to each other.


Celeste Headlee simplifies how to have better conversations.

In this episode, you will learn:

  • Why so many people avoid face-to-face or phone conversations these days and what the consequences are of just sending an email instead of picking up the phone or meeting in person is
  • What the four ingredients are in a great conversation and why
    • honesty
    • brevity 
    • clarity 
    • and a healthy amount of listening
  • Why she believes phone conversations are vital, especially in the workplace
  • How to become a better listener
  • What an “untouchable day” is and how it can help you become a better communicator
  • How to cultivate the power of your voice as business owner to help you grow and scale

Celeste outlines the strategies that have made her a better conversationalist and offers simple tools that will help you improve your own communication skills, as well.


  • be curious
  • check your bias
  • show respect
  • stay the course
  • and end well… Celeste shows us how.



My challenge for you this week:

How are you going to take what you’ve learned in today’s episode and apply it to a tricky conversation you need to have this week? How will you listen more and make the conversation, as a whole, better? Share it with me, privately or publicly. Snap a photo of you doing the thing, and tag @thesimplifiers on Instagram for added accountability and support!

Links, books and apps mentioned:

Book: The Knowledge Illusion: Why We Never Think Alone – Steven Sloman and Philip Fernback

Book: We Need To Talk: How To Have Conversations That Matter – Celeste Headlee

Talk: TED talk by Celeste Headlee – 10 ways to have a better conversation

Favorite quotes from this episode:

[15:08] 3 different types of listening:

  • Evaluative listening – where you are just listening to the extent that you’re trying to figure out if you agree with them or figure out if they’re right or wrong
  • Interpretive listening – where you’re really trying to understand what it is that they’re saying
  • Transformative listening – where you’re actually open to changing your mind and open to being changed by the conversation

– Celeste

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About Celeste

Celeste Headlee is an award-winning journalist, professional speaker, podcaster, and best-selling author of Heard Mentality and We Need To Talk: How To Have Conversations That Matter

In her 20-year career in public radio, she’s anchored many NPR favorite shows, including Tell Me More, Talk of the Nation, All Things Considered, and Weekend Edition. She’s been featured on TODAY, Time, Essence, Elle, BuzzFeed and her TEDx Talk sharing 10 ways to have a better conversation has over 20 million total views to date. 

Celeste is the co-host of PBS’s new weekly series Retro Report that debuted this October and the co-host for season three of the Scene on Radio podcast – MEN.

Where Celeste hangs out online:

Website: celesteheadlee.com

Podcast: Scene on Radio podcast – MEN

Facebook: @celeste.headlee

Instagram: @celesteheadlee


Celeste’s vote for the perfect guest on The Simplifiers Podcast:

Seema Yasmin is a British medical doctor, Emmy Award-winning journalist, author, professor and epidemiologist.

Celeste Headlee

Watch the video version of the episode

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