How to Work with Difficult People (Without Losing Yourself)

The Oprah Podcast | 22 sep 2026 | 00:49:22

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How to Work With Complicated People by Ryan Leak

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