Ryan Leak on The Oprah Podcast: How to Work with Complicated People
September 28, 2026
Shawn Hanks
CEO
Ryan Leak, a New York Times bestselling author and exclusive keynote speaker with Premiere Speakers Bureau, joined Oprah Winfrey on The Oprah Podcast to discuss a challenge nearly every team can recognize: working with complicated people.
Drawing from his book, How to Work with Complicated People: Strategies for Effective Collaboration with (Nearly) Anyone, Ryan explores self-awareness, realistic expectations, communication, leadership, and boundaries.
His starting point is not a strategy for fixing everyone else. It is a question about ourselves: What is it like to work with me?
For leaders and event planners looking for a keynote on teamwork or workplace culture, the conversation offers a look at the ideas behind Ryan's message.
Watch Ryan Leak's Interview on The Oprah Podcast
In the episode, How to Work with Difficult People (Without Losing Yourself), Oprah and Ryan discuss challenging workplace relationships and take questions from listeners about generational differences, leading teams, and setting boundaries.
Source: The Oprah Podcast, published on Oprah's YouTube channel September 22, 2026. Runtime: 49 minutes, 23 seconds.
Watch the full Ryan Leak interview on YouTube.
1. Start With Self-Awareness
Ryan's first principle is that we are all complicated to someone else. Recognizing that possibility changes the starting point of a difficult conversation.
It is easy to identify a colleague's frustrating habits. Ryan asks people to consider the other side of the relationship: how their own preferences, expectations, or communication style might be experienced by someone else.
This is not a claim that every conflict is your fault. It is an invitation to examine the part of the interaction you can influence instead of waiting for the other person to become easier to work with.
For a leadership audience, that makes self-awareness more than a personal-development topic. It becomes a question about the experience leaders create for their teams.
Watch at 6:32: Why Ryan starts with looking at yourself.
2. Choose Understanding Over Trying to Change People
Ryan outlines four responses to a complicated person: avoid them, change them, cancel them, or understand them.
He favors understanding because it begins with curiosity rather than judgment. Instead of deciding that a colleague is simply impossible, ask another question about their perspective, priorities, or experience.
Ryan explains that most people can remember a time when they felt misunderstood and wished someone had asked one more question. He encourages extending that same curiosity to others.
Later in the interview, a listener asks about collaborating across generations. Ryan recommends approaching the conversation as a know-it-some rather than a know-it-all: contribute what you know while remaining interested in what someone else can teach you.
Watch at 7:58: Four ways people respond to complicated coworkers.
3. Try an Expectations Detox
An expectations detox means examining what you expect from other people and whether those expectations are realistic or clearly communicated.
Ryan asks whether we expect others to share identical priorities, read our minds, or change immediately. When those expectations stay unspoken, frustration can build around a standard the other person may not even know exists.
Oprah adds that the conversation can work in both directions. It can be just as important to ask what someone expects of you as it is to explain what you expect of them.
Ryan's point is not to abandon standards. It is to recognize familiar patterns and prepare for them instead of reacting with fresh disbelief every time someone behaves differently than you would prefer.
For a team discussion, this creates a useful distinction: What have we actually agreed to, and what are we merely assuming?
Watch at 14:10: Ryan explains the expectations detox.
4. Make Connection the Goal of Communication
Ryan challenges the assumption that a successful conversation must end with agreement. In difficult conversations, he recommends making connection the goal rather than simply persuading the other person to adopt your position.
He points out that people can ask for better communication while privately hoping it will produce one specific result: the other person agreeing with them.
Shifting the goal does not mean giving up your perspective. It means staying engaged enough to understand the other person and continue the conversation, even when the disagreement remains.
For teams, the distinction is worth discussing before the next difficult meeting: Are we trying to understand one another, or are we waiting for our turn to win the argument?
Watch at 29:54: Connection versus agreement.
5. Set the Standard Instead of Matching the Energy
When a listener asks how to lead a complicated team while balancing performance and kindness, Ryan brings the answer back to the leader's own behavior.
"We don't match the energy. We set the standard."
Ryan Leak, The Oprah Podcast
He describes choosing how to respond rather than returning a passive-aggressive email with another passive-aggressive email. Leaders can decide the tone they want to bring before a difficult interaction begins.
Importantly, Ryan does not present kindness as a substitute for accountability. He describes being honest about performance while communicating that the conversation comes from care, not opposition.
For a leadership conference, this is a practical question to bring into the room: What standard are people learning from the way we respond under pressure?
Watch at 32:28: How leaders set the tone.
6. Keep Curiosity and Boundaries Together
Ryan is clear that collaboration is not possible with everyone. The word nearly in his book's subtitle matters.
When a listener asks about people who seem unwilling to grow, Ryan acknowledges that some are unapproachable, uncoachable, or unapologetic. In those situations, he emphasizes the need for boundaries.
He describes boundaries as doors with locks rather than walls: a way to decide what access someone has to your time and attention. He also explains that it is possible to have empathy for someone while maintaining distance.
This keeps the message from becoming a demand to tolerate every behavior. Working on yourself and trying to understand others do not require pretending that every relationship can be repaired.
Watch at 41:30: When boundaries become necessary.
Bring the Conversation to Your Next Leadership or Team Event
Ryan's How to Work with Complicated People keynote focuses on understanding different personalities, managing conflict, and building more effective collaboration.
For event planners, consider this topic when your audience needs to address strained working relationships, unclear expectations, or the challenge of leading a team with different perspectives.
Use the interview to explore Ryan's thinking, then review the speaking videos on his profile to evaluate his onstage delivery. Share the specific challenge your organization is facing when discussing the program with Premiere.
Suggested follow-through: After the keynote, ask each team to identify one expectation it needs to clarify and one conversation it has been avoiding. Agree on a next step and a time to revisit progress. This is an event-planning suggestion, not a separate framework attributed to Ryan.
As the podcast closes, Oprah tells Ryan, "So many really vital lessons in this book." The conversation returns to a hopeful idea: you do not have to wait for everyone else to change before beginning your own growth.
Frequently Asked Questions About Ryan Leak's Oprah Interview
Which book does Ryan Leak discuss on The Oprah Podcast?
Ryan discusses How to Work with Complicated People: Strategies for Effective Collaboration with (Nearly) Anyone. The conversation covers self-awareness, expectations, communication, leadership, and boundaries in workplace relationships.
Can we book Ryan Leak to speak about workplace collaboration?
Yes. Ryan offers a keynote titled How to Work with Complicated People and is exclusively represented by Premiere Speakers Bureau. Share your audience, event theme, and desired outcome to discuss whether the program fits your meeting.
How do we request Ryan Leak's speaking fee and availability?
Contact Premiere Speakers Bureau with your event date or date range, location, audience, format, and budget range. Ryan's speaking fee is provided by inquiry. Ask what the quote includes and confirm any travel or additional program requirements.
Book Ryan Leak for Your Next Event
Looking for a speaker who can help your audience approach workplace relationships with more self-awareness, curiosity, and accountability?
Premiere Speakers Bureau exclusively represents Ryan Leak. Our team can help you explore his keynote programs, review speaking videos, and check availability and current fees for your event.
