How to Work with Difficult People (Without Losing Yourself)

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How to Work With Complicated People by Ryan Leak
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New York Times bestselling author Ryan Leak joins Oprah at her tea house for a practical conversation about navigating difficult workplace relationships. Drawing from his book How to Work with Complicated People Ryan shares why the people we work with, more than the work itself, often determine how fulfilled we feel on the job. He breaks down four strategies for working through challenging dynamics, introduces the idea of an “expectations detox” and offers a powerful reminder: we’re all complicated to someone else. This conversation isn’t about fixing other people, it’s about growing ourselves through greater self-awareness, understanding, and emotional maturity. Oprah and Ryan are also joined by listeners with real workplace dilemmas, tackling questions about bridging generational divides, leading with empathy while still meeting goals and setting healthy boundaries with colleagues who seem beyond complicated. It’s a practical and relatable conversation filled with tools to help anyone build stronger relationships at work and beyond.

00:00:00 - Welcome Ryan Leak, author of “How to Work with Complicated People”
00:04:50 - People problems at work
00:07:00 -We never think we’re the problem
00:07:58 - 4 ways people deal with complicated people
00:11:30 - Importance of partnership
00:12:20 - Expectations detox
00:14:50 - Our unrealistic expectations
00:15:38 - What should we do in the moment
00:18:20 - Be the adult in the room
00:21:00 - Generational differences
00:24:00 - Questions to ask
00:27:50 - How to communicate better
00:29:20 - How to set the tone as a leader
00:33:00 - You choose your reaction
00:34:28 - Why half of Americans quit
00:39:10 - When is it not possible
00:43:00 - How to grow yourself
00:44:40 - One word Ryan lives by

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Listen to the full podcast:
open.spotify.com/show/0tEVrfNp92a7lbjDe6GMLI
podcasts.apple.com/us/podcast/the-oprah-podcas…