How to make difficult conversations simpler (Part 2 with Travis Dalrymple)

How to make difficult conversations simpler (Part 2 with Travis Dalrymple)

From The Art and Science of Difficult Conversations by Chris Wong & Lucie Tesarova

March 24, 2026 · 23 min · Season 3

About this episode

In this episode, Chris, Lucie, and Travis discuss practical strategies for simplifying difficult conversations and improving communication in leadership.

Summary:   In part 2 of their conversation, Chris, Lucie, and Travis walk through practical strategies for having difficult conversations, asking effective questions, and improving communication in leadership. They also role play a performance conversation to show how asking questions and remaining curious can lead to powerful insights.  In this episode, learn how to:   Ask questions instead of making assumptions to understand others better.   Use silence intentionally to give space for processing during conversations.   Frame questions to avoid defensiveness, especially with sensitive topics.   Prepare for difficult conversations by scheduling positive activities afterward.   Practice curiosity and ask 'what' and 'how' questions to explore motivations.     About Travis : Travis Dalrymple  is a leadership advisor, author of  How To Suck As A Leader , and the founder of The Leadership Lab—a program that helps small business owners and team leads stop managing people and start actually leading them. From placing 3rd on  America’s Got Talent  to leading high-performing teams in the business world, Travis blends…

People in this episode

Hosts: Chris Wong, Lucie Tesarova

Guest: Travis Dalrymple

Topics covered

  • difficult conversations
  • communication strategies
  • leadership
  • curiosity
  • performance conversations

Keywords

  • difficult conversations
  • communication
  • leadership
  • curiosity
  • performance

Mentioned in this episode

Books & works: How To Suck As A Leader

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