How to Work with Difficult People (Without Losing Yourself)

September 22, 2026

AI Summary

5 min read

In a research study for his book How to Work with Complicated People, Ryan Leak asked participants to define the word "complicated." One person wrote a single name: Leslie. Another wrote: Jamal. The finding was blunt: when people talk about complicated colleagues, they are not describing a personality type or a communication style. They are describing a specific person who has already hurt or frustrated them. The first step Leak recommends is not a technique for managing that person—it is a mirror. As he tells Oprah in this episode, "You could be somebody's name. On the other side of me, Ryan could be complicated."

The expectations detox

A major source of workplace frustration, Leak argues, is not bad behavior but mismatched expectations. People walk around with an unspoken inner definition of what is "right" or "normal," and when a colleague violates it—by hitting reply all, by speaking in a meeting, by failing to read their mind—the reaction is "I can't believe." Leak’s remedy is something he calls an expectations detox: you begin asking yourself what you actually expect from the people around you. Do you expect them to share your priorities? To change instantly? To never make a social misstep? "You stop acting so shocked when people have a bad attitude or don't have the same preferences as you," Leak says. The goal is to see complicated behavior coming and treat it a

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What you'll learn

1 (00:00) **Episode Introduction & The Core Problem** - Oprah sets up the episode: most people spend 90,000 hours at work, and nearly half quit because of their boss. She introduces guest Ryan Leak and his book *How to Work with Complicated People*.
2 (02:42) **Why This Book Exists** - Ryan explains the two cultural forces that drove him to write the book: the rise of polarizing topics without emotional tools, and the 90,000 hours people spend at work.
3 (05:08) **Why "Complicated" and Not "Asshole"** - Ryan explains why the word "complicated" was chosen based on his research, and why you must start with yourself.
4 (08:08) **The Four Options for Dealing with Difficult People** - Ryan lays out the four strategies people use: avoid, change, cancel, or understand.
5 (09:08) **Oprah's Lesson on "Changing" People** - Oprah shares a personal story from her talk show about the backlash she received for trying to "change your life."
6 (13:13) **The Power of "With" and the Expectations Detox** - Ryan explains why the word "with" in the title is crucial, and introduces the concept of an "expectations detox."
7 (17:20) **What to Do When You Get Triggered** - Ryan provides a practical three-step process for managing triggers in the moment.

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Show Notes

BUY THE BOOK!

How to Work With Complicated People by Ryan Leak

https://amzn.to/4y8aXDB

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