Squiggly Careers

3 Hard Work Conversations & How To Handle Each One with Confidence


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This week, Helen and Sarah revisit insights from three podcast guests—Amy Gallo, Celeste Headlee, and Dr. Sunita Sah—to tackle a topic many of us shy away from: difficult conversations.

From team conflicts and moments of defensiveness to speaking up when something feels off, these everyday challenges can shape how we collaborate, grow, and thrive.

In this episode, you’ll learn practical strategies to handle tension with ease: turning irritation into curiosity, using affirmations to stay grounded, and recognising the early “tension signals” that signal it’s time to speak up. You’ll learn how to navigate disagreements without defensiveness, communicate with confidence, and act in alignment with your values—even when it’s uncomfortable.


Episode 516


🦞 Pre-order Learn Like A Lobster:

🇺🇸 PRH US – https://bit.ly/3KxTeBn

🇬🇧 Amazon UK – https://amzn.to/3KcRZaR


📚 Resources Mentioned

Getting Along by Amy Gallo - https://bit.ly/43XtfdJ

Celeste Headlee’s TEDx talk: 10 Ways to Have a Better Conversation - https://youtu.be/R1vskiVDwl4?si=3PFsc2v2v1xK9fy_

Dr. Sunita Sah’s Defy: The Power of No In A World That Demands Yes - https://bit.ly/3KfPuF7

How to Preempt Team Conflict — Harvard Business Review - https://hbr.org/2016/06/how-to-preempt-team-conflict


Previous Squiggly Careers interviews with:

Amy Gallo - https://youtu.be/iO7Q1g7u0SY?si=Pm5srmx-7AgkjIaP

Celeste Headlee - https://www.youtube.com/watch?v=IC9kT476GL4

Dr. Sunita Sah - https://open.spotify.com/episode/6ELoznhCWtk5vlONAlY3wC?si=z6i8C1JOT_21aQ0HeNiZzQ


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