The Oprah Podcast - How to Work with Difficult People (Without Losing Yourself)

Episode Date: September 22, 2026

BUY THE BOOK!How to Work With Complicated People by Ryan Leakhttps://amzn.to/4y8aXDBNew 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 work00:07:00 -We never think we’re the problem00:07:58 - 4 ways people deal with complicated people 00:11:30 - Importance of partnership 00:12:20 - Expectations detox 00:14:50 - Our unrealistic expectations00:15:38 - What should we do in the moment 00:18:20 - Be the adult in the room00:21:00 - Generational differences00:24:00 - Questions to ask00:27:50 - How to communicate better 00:29:20 - How to set the tone as a leader00:33:00 - You choose your reaction 00:34:28 - Why half of Americans quit 00:39:10 - When is it not possible00:43:00 - How to grow yourself 00:44:40 - One word Ryan lives by Follow Oprah Winfrey on Social:https://www.instagram.com/oprahpodcast/ https://www.facebook.com/oprahpodcast/https://www.instagram.com/oprah/?hl=enhttps://www.facebook.com/oprahwinfrey/Listen to the full podcast: https://open.spotify.com/show/0tEVrfNp92a7lbjDe6GMLIhttps://podcasts.apple.com/us/podcast/the-oprah-podcast/id1782960381

This episode of the Oprah podcast is presented by our partner, Geico. Statistics say chances are very, very, very, very high that there is somebody at work who is driving you crazy. You're going to spend 90,000 hours of your life at work. And what determines if somebody loves or enjoys their job is not often the job description. It's often the people that they have to work with. Some people are certified crazy and you cannot work with everybody. So in your research, one of the things you found, I heard, was that nearly half of Americans quit their jobs, really, because of their boss. And you suggest what you call an expectations detox.

I love this so much because I've done this many times in my life. This is so key. Like, you stop acting so shocked when people have a bad attitude or don't have the same preferences as you. Is that right there, Ryan? That's going to help a lot of people. Hi, everybody, and welcome to the Oprah podcast, and I thank you for joining us here. I'm really so excited for you to meet my guest today because if you're listening or watching us and you are a working person, statistics say that the chances are very, very, very, very high, like 80% high, that there is somebody at work who is driving you crazy.

And I know just hearing me say that, that person just popped in your head right now. And maybe they have a toxic personality, or they take credit for your ideas, or they're always just either snarky, condescending, or just annoying, or you found out that they talk stuff about you behind your back, or they don't pull their own weight. It is frustrating, and it is so annoying. And I know because I have dealt with all kinds of working relationships, from Fortune 100 boardrooms to professional locker rooms, Ryan Leek,

is a sought-after speaker and a best-selling author. And his latest book, How to Work with Complicated People, Strategies, Not Just Talking About It, But Strategies for Effective Collaboration with Nearly Anyone. It offers a better way to... This is going to help you start setting boundaries, like actually give you the words to set boundaries, to communicate, and also to detox at work. because a lot of people just take it all home, right? And even if you think you're surrounded by idiots,

this book will work for you. Welcome to the podcast. Oprah, it is an absolute pleasure to be here. What was going on in your own life that you knew you had to write this? Oh, well, I felt bad for my team that has to work with me. And, you know, traveling and speaking and working with companies all around the world and just having a phone and being on social media, I noticed a couple of things were happening in culture that I thought we needed some help with.

Number one, I started to notice that we were given, especially over the last decade, I would say more polarizing subjects than ever before without the requisite emotional tools to actually have discussions around these subjects. And so you started to see, especially online, subjects moving from us having a disagreement about something and it started to move into disrespect. Yeah. So you saw this insolity. Disrespect, disregard.

Oh, name calling. Yeah, just it turned into a thing. 100%. I mean, I think we've all had that moment. Yeah. We were just watching it and going, it's getting worse. And so I think I've worked with a company. They have this framework where they say,

hey, this is how we have high stakes conversations. We have things that we will die for. We have things that we will defend. And we have things that we will discuss. Well, I started to see that a lot of the subjects that we were given, it was all hills to die on. Yes. Every comment. It's like, I got to have a take on this particular subject.

It's like, I don't think you have to have a take on every single subject. And so I wrote this book to say, hey, how can we get off the hill and quit trying to die on the hill? And how can we have a cup of coffee and have a discussion? So that was the first thing that was going on. And the second thing is what we've discovered in research is that, well, you're going to spend 90,000 hours of your. your life at work. 90,000 hours of your life is going to be at work. And what determines if somebody loves or enjoys their job is not often the job description. It's often the people that they have to work with. So we said, hey, if we could give a playbook to people to do the people part of their job,

well, then maybe they could enjoy what is a significant portion of their life. Well, when I saw this title, how to work with complicated people. Yeah. Great title, by the way. Thank you. It's a New York Times bestseller. It is. deserves to be, because it's clearly striking a nerve. Yeah. And I know firsthand that nearly all work-related problems are actually people problems trying to be worked out at work. Is that what you've also discovered?

Absolutely. Yes. Yeah, you see a lot of people who are trying to navigate change, trying to navigate AI, trying to navigate technology changes all throughout all kinds of industries. but at the end of the day, they're people problems. And oftentimes you're going to be sitting across from somebody who thinks differently than you, works differently than you, is from a different generation than you.

And we all have to have a great plan for what we're going to do when we're sitting across from different. And I like the fact that you use, Ryan, the word complicated. You could have said, an assholes, how to work with assholes, how to work with jerks, how to work with, okay, a lot of words. But anyway, so why did you choose the word complicated? Well, it was the word that came up a lot in our research. Whenever I would be sitting across from somebody and say,

so tell me about this person that you're having a challenge with. They say, well, they're not bad. They're complicated. And so it was somebody that had patterns and had perspectives that just didn't vibe well with theirs, and they couldn't find a word to use. And I said, is it complicated? Yeah, it is very complicated because, you know,

It's, I don't want to offend them, but I also want to be honest. The times have changed. Pre-COVID, post-COVID. Are we working virtually? Are we working in person? And so what we kept finding is that it kept being more and more complicated. Now, this is the thing. You start the book by saying, when we're dealing with difficult people,

the first person you need to look at is yourself, even though nobody wants to hear that. Because they're like, this isn't my problem. This is you. And you write, we are all weird. We are all odd, irritating or baffling to someone else. Yeah. So do people have a hard time with this, with this start with yourself? Yeah.

Do people have a hard time when you say, let's first take a look at you. Yeah. Why are you having this problem? Yeah, well, it's hard to look in the mirror. Because when you think about somebody that, if we start talking about boundaries, if we start talking about somebody that needs to be challenged, if we start talking about somebody that needs correction, like we all have people in our life that we go. They shouldn't have even gotten this job.

They should never get a microphone. They need to get their act together. The problem is none of us think we're the person. Right. We think it's always somebody else. So by starting with yourself, you are automatically on first base with working with complicated people. Because if I start with myself and go, you know what? On the other side of me, I bet it's not as easy and as ideal as I think it is.

If I start with, well, maybe on the other side of me, it's a little complicated. Well, then I'm going to have grace for your complexities. But if I think I'm the hero of my own story. Yeah. But what if I know that I can be challenging and I know that I can be intimidating and I know all those things. Yeah. But I just want to get the job done. Yeah.

And don't want to have to deal with your complications. So what is the best strategy when you're dealing with somebody who doesn't understand that? Well, at some point, we all have different strategies for how we're going to deal with complicated. You say most people use four strategies to deal with a complicated person. What are they? And what is the one that works? So the first one you can do is avoid them, right? Yeah.

Except you can't. You can't. I've found that complicated people are unavoidable. Yes. As much as you try. You can do everything in your power. You're going to run into them. You have to deal with them.

They will find you. They will find you. Every single time. Okay. Second thing you can do is you can try and change them. You cannot. Which good luck. But most people, to do that, you have to twist their arm.

And nobody likes having their arm twisted. So good luck trying to change them. You may be able to change some behavior. You can inspire it. Yeah. You can inspire it. You can inspire it. But, I mean, imagine if somebody walked up to you and said, hey, I'm really looking forward to changing you soon.

You can be like, what? You're not changing me. Nobody even really wants to be changed, but they also want to try to change. The fact that you just mentioned that reminds me of the year we, every year on the Oprah show, we always considered ourselves the Oprah show, which ended 15 years ago. So I'm not trying to live in the past. But for 25 years, I did the show. And every year, our goal was to.

to do a better job the next year than we did before. I never considered anybody else competition. We were competing with ourselves. And one year, and we would have themes every year, and one year, because people used to come up to me and say, oh, I watched this show, it changed my life, it changed my life. This show changed my life. So I said, oh, let's call this year, Change Your Life TV.

Yeah. That's what we're talking about. This is the year to change your life. We'll be right back. The biggest backlash ever. Because people said, how dare you tell me that you changed? my life. Wow. So this is what I learned from that. Don't tell nobody you changed your life. Let them tell you that you change your life. It's not my job to tell you I'm going to change

your life. Nobody wants to be changed or to think that that's your goal is to change them. Well, when we use that idea of like the world would be a better place if everybody else just changed. It's a terrible mantra to live by it. Again, you could try. I just don't think it's going to help you actually grow. The third option is you could cancel them. And if you cancel them, that means, well, I'm just going to cut you off. Yeah. That's what you could do with a complicated person. Yeah.

The problem with cancellation is this. The cancellation and avoidance is sort of the same thing, right? Well, cancellation is where I say I'm done with you altogether. Yeah. The problem with cancellation is it's bad math because none of us want to be on the other side of being canceled. In fact, if I cut somebody off, I have all the rights to do that. But if somebody cuts me off, I say, whoa, whoa, whoa, whoa, whoa, I want my day in court. I want to be able to say, no, no, you misread my email.

That's not what I meant in that text message. No, you want a second chance, which is why the fourth strategy works, which is you could try and understand them. Understanding means I'm going to move towards this complicated person with curiosity instead of judgment. The reason that this is important is because each and every one of us has all had a moment in our life where we were misunderstood. And in that moment, all we did, all we wanted was somebody to ask for one more question,

to be just a little bit more curious. And so people have this idea that, oh, I'm going to move away from complicated people, but I'm like, actually, you'd be surprised what happens when you move towards them. You might actually learn something new about this person that you didn't know before. And I've learned time and time again,

somebody that used to be very, very complicated in my world, the more I actually got to know them, they actually just became a name, and it wasn't complicated. Our listeners tell us that the podcast is resonating with you and is serving as a bright spot in your day, That means a lot to me. So here's the thing.

I would really appreciate it if you like and subscribe to the Oprah podcast on YouTube or wherever you podcast. It's just a quick tap of the subscribe button, and that way you won't miss an episode in your cue. You don't have to pay anything. I know subscribe usually means you're paying something, but this time it means you just are notified when there's something new. There are many more to come that we're excited about. So thank you for watching and listening. Those of you watch the Oprah podcast or listen to us, you know, every story we share, every guest we welcome is chosen with purpose. And when people share their stories, we're reminded that we're not alone in this journey call life.

As the official insurance partner of the podcast, the folks at Daico understand that the way we move through life and who we move through it with matters. And I know that life starts to move even faster as a new school year begins. Fall routines get underway. The calendar fills up. Whether you're waiting in the school pickup line, loading up the car for a weekend getaway, taking a quiet drive home after a hard day or cheering on your son or daughter from the sidelines.

These moments remind us the road is not always a straight line. Geico is there with insurance design to help keep you covered along the way. Because life happens, and with the right support, we all just keep driving forward. And that, dear listener, is everything. You say,

with is the key word in this title of your book. Why? Well, because how to work with screams partnership. It immediately tells you, hey, this person that I have sitting across from me

is not my enemy. I'm working with, we're all on the same team. I'm not working against you. I'm not trying to work around you. I'm trying to work with you. It makes us have a collaborative

mindset. Well, I love on page 54 when you say when we view people as complicated, it's often because they don't meet our expectations, something about them, their personality, their communication style, their manners, their leadership, their social skills, their behavior doesn't match our inner definition of what is right or normal. And you suggest what you call an expectations detox. I love this so much because I've done this. Many times in my life, please share this. Yeah, so an expectations detox is where you begin to look at the world around you and begin to ask yourself the question, what am I expecting of the people around me?

Do I expect them to have identical priorities? Do I expect them to be mind readers? Do I expect them to change instantly? It's like, no, it's what we discovered in our research is we kept hearing the same phrase over and over and over again. And it was the phrase, I can't believe. I can't believe they would hit reply all. I can't believe they would say that in front of my boss. I can't believe my husband doesn't know where the kid's shoes are.

I can't believe my in-laws would say that. I can't believe. I can't believe. We just came alongside and said, I think you should start believing them. Somebody that you know very well said if someone shows you who they are. Believe them. Believe them. All right. Bring up in Maya Angelou here.

So we said, hey, if you can begin to taper your expectations to be able to say, hey, I'm actually, I actually see complicated coming a mile away. In fact, it's like, you've worked with these people for a very, very long time. You've been married to this person. You've dated this person for a long time. I'm like, you stop acting so shocked when people have a bad attitude or don't have the same preferences as you. It's like, no, I've actually tapered my expectations.

And if you can expect complicated and see it coming a mile away, then you can prepare for complicated people. Well, and I think that works in the opposite, too. I recently had a conversation with someone, a complicated conversation, in a complicated relationship, where I was saying to the person, tell me,

I had read your book, I said, so tell me what your expectations are, because the reason why this isn't working is because you have an expectation of me that I don't think I'm actually willing to fulfill. And then the person said, oh, I don't have any expectations.

And I said, and you also apparently have a lack of self-awareness. That's right. Because you actually do have multiple expectations that you're putting on me and expecting me to know what those expectations are and to fulfill them. Yeah. So it works the opposite. Yeah.

Totally. Because I think so many times people are disappointed in people because they don't fulfill their expectations, but they're not even clear about what those expectations are. Absolutely. And I would say that most people's expectations are silent. Yes. In fact, I think that most of us walk around the world, and we expect people to be two things they rarely are.

Simple and perfect, except nobody's that. In fact, the only options you have for working with people on this planet are complicated people. In fact, some people will say, you know, say, hey, I wrote a book called How to Work with Complicated People. And this is what happens every single time. They look in the sky, and they go, I need that book. and they see somebody. They see a person. They don't even have a definition of what complicated is.

They just go, oh, I see that person. But nobody, nobody looks up and goes, somebody needs that book for me. Yeah. And I think that's where the girls is really found. Okay. So we have all dealt with this. You get that email.

That's right. And sends you over the edge. Or you get a certain look from your boss or colleague. Yeah. And you're like, what was that all about? What is she really trying to say? and you start spiraling when somebody triggers you. What should we do in that moment?

Well, one, you have full permission to call a timeout. I think, number one, you got to take a deep breath. What's actually happening when we get triggered is our nervous system is out of whack. And you are not going to outthink a triggered body. You have to take a deep breath. The second thing I think you should do is you should really name what's happening.

Because when you give a name to your, your trigger, it actually loses its power. All of us have different triggers. It could be professional embarrassment. It could be insecurity about how we look. It could be a compliment that somebody else got that we wish they had given us. It could be somebody else getting promoted. So being able to name that thing helps you step outside of it, right? Because you're talking about it. And now it's... So shouldn't you in that moment say, what just happened here? Yes. Why did that trigger me? Why am I feeling this way? That's the first question you should say. Why am I feeling this way? Oh, most people are going to say, oh, because you're

because he or she pissed me off. Yes. Okay. And then the question should be, but why did it piss me off? Yes. What is really going on underneath the surface? Absolutely.

I feel humiliated or I feel embarrassed or I feel, you know, that. I feel shame. I feel shame. Those are the questions you should be asking yourself. Absolutely. And then from there you want to go, how much power am I going to let this have over the rest of my day, my week, my life?

Yeah. Because once we name it and we look at it, we're going to go, Am I going to let Keith, like, determine the rest of my biggest? I'm sure not going to let Keith. He's behind the camera. I'm sure not going to let Keith. This is the thing I learned so many years ago.

I've been around so long that I have so many stories. But I remember I was holding a grudge against somebody, and I saw them. I was walking down Michigan Avenue in Chicago. Wow. And that person was on the other side of the street. And they were, like, just swinging their bag. Live in life. Live in life.

Turned. Went into the table. Tiffany store. The Tiffany store. Spending money. Spending money. And I'm like, I'm walking around here mad, thinking that person's also walking around mad, feeling my whatever, whatever, and realize they're happy. They're gone on with their lives. Yeah. The thing that's triggered you from an email or a text message that somebody said, they sent to you at 718 a.m. And now is 433 in the afternoon, and you're still thinking about it, thinking about it, thinking about it. They're going on.

They're swinging their pocketbook. That's right. Going into Tiffany's. Yeah. They're not thinking about you. They're not thinking about you. Yeah. Yeah.

The last thing I would say about whenever we find ourselves being triggered, we have to be the adults in the room. We have to be the adults in the room because there is a what psychologists would call age regression. It's where you and I turn into eight, nine-year-old. That's right. You turn into however old you were, when that trigger first was implanted in the back of your brain. Absolutely. Yeah. and whatever that thing is.

And it happens to me all the time. You know, my, I turn nine years old really fast because when I was nine years old, my father unfortunately suffered a stroke. Our household income was cut in half. And I remember going to my mother and just being like, I don't want to be a burden to my mom

who now has to take care of my dad and my two older brothers. That day, I became wildly independent. That day I became an entrepreneur. That little boy is what allows me to do what I do now. Right. But also being that independent, whenever I feel triggered, whenever I feel disrespected, where my age regression really pops in is I go, I don't need you.

I don't need you. If a client starts talking crazy to me, I go, I don't need to be here. That's my age regression. You immediately go to that. I immediately go back to I don't need nobody. But I do need people. Yeah. And so if you're triggered.

That's what that right there, Ryan. That's going to help a lot of people. That's going to help a lot of people. Yeah, I would just encourage people. Just that specific example is going to help a lot of people because a lot of people immediately go into that. Well, okay, then I don't want to have anything to do with you either. Yeah, that thing when you really do.

Yeah, I mean, you be the adults in the room. If you're going to have an adult conversation, make sure the adult version of you is in the room when it happens. Because now you've just decided, I realize there's some things that happened in my childhood that I wish didn't. But I'm adult Ryan now, so I can have an adult conversation. Yes, and so people use this now.

The trigger has become the word. I just got triggered. I just got triggered. I just got triggered. But not willing to examine what does that really mean. Yeah. Because people assume, I think, when I've heard people use it, you know, so casually that way, oh, that person had no right to trigger me.

Or how dare they trigger me? Yeah. Yeah. When the trigger is showing up for. actually your benefit to examine and to actually become more of an adult. Yeah. It's an opportunity. It's an opportunity.

If you let it. Yeah. So some of our listeners have questions for you. Brian is an eighth grade teacher in Michigan. Yeah. And Brian is joining us. Hi, Brian. What's up, Brian?

From the class trip to Washington, D.C., the classic eighth grade trip to D.C. God bless you. That's right. Thank you. We are having a great time here. We are leaving tomorrow night, but we are just running through the Capitol for the first time with these kids and that couldn't be more of a blast. That's great. What's going on with you at work?

So I am absolutely having a generational divide at my work. So for context, I'm 26 years old. It is my first year teaching. Congratulations. I think that's great that you chose that profession. That's great. Thank you.

It's the best choice for me. And we are nearing the end of year one. And for reference, I am one of a few teachers in my 20s. The other four are the only others in their 20s. The average age is probably closer to 50, and some of my colleagues actually were my eighth grade teachers, which is ironic. Crazy. And, you know, we, I'm so honored and grateful to be doing what I'm doing with the people that I'm with, and especially with the students. And we all bring so much value to the table.

I think that my older colleagues bring wisdom and experience because they've done this a few times. And the younger teachers bring innovation and some new ideas. but we also have differences in how we approach education and some of our principles. And my question, as I'm navigating this relationship with all of my colleagues, is how do we allow the younger workforce members to earn a seat at the professional table to advocate for their ideas and their approaches while also honoring the wisdom and experience of our colleagues and inviting them to be a part of that collaboration? especially when we're trying to do what's best for the kids at the end of the day.

That's awesome. Well, Brian, I think the word you just used is already going to be huge for you, which is, you know, you're just already honoring of the older generation, which I think is going to earn you some influence. The other thing that's an interesting paradox that I think all of us have to navigate in the workforce is we get to where we are by having knowledge and competence. But what comes with knowledge and competence is sometimes arrogant, And so you actually need humility to come in there.

And so it's interesting, you can sometimes feel this pressure to be a know-it-all. I love this idea of being a know-it-sum, which means there's some things that I know, but I'm also curious about a lot of other things. Here's the funny thing. I love that. I'm a know-it-some. I'm a know-it-some. Here's an interesting paradox about it.

When you're a know-it-all, like when you're really, really smart, like you work really hard to be really, really smart. The only problem is nobody likes being around a know-it-all. So you've worked really hard to be a person that nobody wants to be around. So when you're at that table, there is something that you know. There is value that you have to offer. But being to know at some is there's a curiosity. A question that you could ask them that I've been asking a lot of people that I just love is, what's something you're unlearning right now?

What's something you're unlearning? What's something you believe 10 years ago that today you go, I don't know about that? What are you unlearning? What you're showing is a great honor and respect for them, but you're also getting their wheels turning. Number one, if they don't have an answer to that question, well, that means they're actually not learning anything new.

But if they also don't have an answer to that question, they might go, is there something that I'm missing? Another question you could ask them, in such an honoring way, you could go, hey, thanks for what you did for me in eighth grade. Hey, what do you think's changed since I was in the eighth grader? Now that we're trying to serve eighth graders, what have you noticed about my generation

that's different from the eighth graders that we have in our classrooms right now. Again, you're still honoring, but now you have a posture of you're inviting them to a table to have a conversation versus a, man, these are some of all of the things that we need to do. So what you're trying to do right now is by influence in your organization,

and I think by being a know-it-sum, I think it's really going to help you add value to it. You know, I had Simon Seneca here at the T-house table recently, and he was saying that what, the gen X generation needs to understand, to echo what you're saying, about Gen Z generation and, you know, other generations coming up, is that it was a completely different time. So when you're 50 years old, 60 years old,

you think everybody is operating on the same, from the same worldview because you had the same world experiences. And he was just saying that your generation, in particular, Brian has seen your parents grow up and get layoffs. They've seen that the Golden Watch era of working for one company for multiple years and being rewarded for that. It didn't pay off so well. They've just seen so many things that prior generations didn't experience. I mean, all the kids your teaching have grown up from birth with technology, cell phones and all of that,

which makes a very different world and world experience for them. And I think what Ryan is suggesting here is a fantastic opportunity for y'all to get together in the teachers' lounge, whatever y'all do in there, talking about other students, to actually have a real conversation about the difference between when you were there and if you start out complimenting them, if you start out sharing how much you got from them, just as Ryan has suggested, and then lead into how do you think it's different? And do you think that you would be teaching the same to us then as you're teaching now? I think that opens the door for them to see it differently. Because that's really what you're trying to get them to do.

It's to see it differently and to, right? Absolutely. And to bring them along without offending them. Without like, y'all are old, without saying y'all are old. I think that absolutely makes sense to me. I mean, it has been just so rewarding to do that full circle experience with them. But I also want to maximize the time that I have left, especially as they're getting close to retirement. And one day, I won't have them as a resource moving forward.

That's fantastic. Love it. Well, I think these are some good takeaways, right? Absolutely. I mean, we are already looking forward to next year, but we're coming to the end of Chapter 1. And I really just want to start utilizing some of these approaches for hopefully a lot. and successful career with my kids. I think that's great.

Thank you. I love teachers. Thank you. Thank you so much, Brian. Thank you. Brian. Appreciate you. Okay, thank you, Ryan.

So you devote a whole entire chapter to communication, right? Right. And you've concluded, what, that most people are pretty flawed at communicating. And that's the word everybody always used, we just need better communication. Yeah. Yeah. We just need to have better communication. So how do it?

people have better, how do people become better communicators? Well, first, I think we have to establish what is going to be the goal of the communication. What is the goal of this conversation? What does that really mean? I think that's, I think, in all these circumstances, people need to clarify, what does that mean? Because the word communication may mean one thing to you. Sure. What you're sharing and may mean something else to me. Yeah, I would say in this context, we're talking about having conversations with difficult people or with a complicated person. Yeah. And, and, and, you're saying, And if we're honest about what our actual goal is with these conversations, it's actually agreement. I actually have something.

And low-key, I actually really want you to agree with me. And so that's my underlying goal of the conversation. I think if we're going to be effective in communication, we have to shift the goal. I don't think the goal should be, I'm trying to get you to agree with me. I think the goal should be connection. Okay. And the minute we lose connection, it's going to be very, very difficult. for us to have.

Communication. A difficult conversation for sure. Absolutely. So Nadia joins us from Houston. Nadia, what's going on with you? Hi there. Hi, Oprah. Hi, Ryan.

Thanks for including me in the conversation. So I have been in HR for about 25 years. In the past 15 years, I've been helping big tech organizations recruit their executive leaders. So I know a thing or two about complicated people. That's right. I have to say, one of my favorite

things in the book is acknowledging that we too are complicated in someone's story. I found myself getting blocked with someone today and I was able to go, wait, you know, I'm probably complicated for them too. And that allowed me to diffuse the situation and remove the emotion. And then we could work towards solving an outcome. So thank you for that. Yes. But my question for you is, there is so much rhetoric around complicated bosses, complicated peers.

But I don't hear a lot of conversations. around leading complicated teams. And let's unpack that a bit. It could be they are not intentionally complicated. It could be macro, micro things, org changes, difficult economy. But as a leader of teams, how do I drive performance, you know, make sure we're hitting the goals that we've set without losing my humanity or my like human-centered kindness.

I'd love to get your perspective. Yeah, you know, you've got quite a few layers there. And, one, thank you for your vulnerability and even just being able to to come on the show, I think part of it is leaders have to set the tone. And that's what people often forget, that they are the absolute tone setter. Your attitude is the number one thing that will set the tone for every single room that you lead. And so even in our research, we thought politics would be the number one thing that would determine if a person was complicated to work with or not, complicated or enjoyable.

It was actually dead last in our research. We then thought it would be personality profiles, like, oh, I'm introverted, you're extroverted, or maybe you're ambiverted, and you don't know until you've had a cup of coffee. Like, we thought it was going to be those things. That was third to last. The number one thing that determined if somebody was enjoyable or complicated to work with was attitude. Attitude. And the reason I love that is it's because it's the number one thing you can actually control.

And so whenever you're dealing with somebody that might be disgruntled or dealing with somebody that might be angry or somebody that's passive aggressive, the temptation is to match the energy. The phrase I like to use is, we don't match the energy, we set the standard. I don't match passive aggressive email for passive aggressive email. You might have a funky attitude. I don't mean I'm going to have a funky attitude. I have already made a decision about my attitude. And what we have learned is that attitudes are contagious.

In fact, in the book, we talk about how one compliment can actually spread across 8,000 interactions within 24 hours. especially for somebody like you who leads teams because you decided to set the tone. You decided that you were going to start off meetings with fun ice breakers. You decided you were going to lead the culture. You don't let somebody else determine that temperature. You do.

You have chosen your attitude. So for me, I travel and speak for a living, which means I'm at the number one place in the world every single day where the angriest people go every day. The airport. Let me tell you something. People be mad at the airport, okay? They be mad, mad, mad.

They mad at the weather, they mad at the gate agent, they mad at TSA, they mad at everybody. And so I've just made a decision that since this is where I work, I'm not going to be mad. I'm expecting it to not go well. I'm expecting the delay. I'm expecting whether to not go well. And then all of a sudden, you know, agent comes over the announcer, oh, sorry, this plane has been delayed. And then everybody, and they lose their minds. I'm like, no, I've just decided I'm going to have a great day at the airport.

you get to choose the energy you bring every single day. Do not match the energy, set the standard. When you set the standard, it allows you to step into some of those difficult conversations to be able to say, hey, I care enough about you to be honest with you. And I can say that with a smile on my face. I'm not against you. I care enough about you to be honest with you. And if I'm honest, I don't think you're giving your best.

And in light of the goals that you want to accomplish in your career and in your life, in line of the promotion that you want, hey, we've got to raise the bar. You're better than that. And so I think you can still speak with kindness, but you've still got a smile on your face, and you've already made a decision about who you're going to be when you show up. I think this is so great. Don't you think this is great, Nadia? And also, for the hundreds of little aggressions or microaggressions that people get,

That's right. And I'm not just talking about racial microaggressions. I mean, microaggressions you get from your colleagues. All time. Or you get them in text and so forth. You don't have, I think if you just take a pause, you don't have to respond to the text or the email with the same energy that's coming at you. That's what you're saying.

That's right. You have a choice to literally flip the energy around and do something more positive. I think that's terrific. Amazing. Set the standard. I love it. Thank you. You're welcome.

You're welcome. So in your research, one of the things you found. I heard was that nearly half of Americans quit their jobs, really, because of their boss. Oh, yeah. Big time. Yeah. It's amazing. Just a little under half have skipped a day at work because they were having to deal with a complicated person. You say people don't quit jobs. They quit bosses. That's right. They quit leaders. Yeah. No question about it. What do you want to say about this? It's interesting because, you know, it goes back to this idea of it's looking because the leadership starts at the top. It does.

Yeah. And their relationship with that person that's in charge of them really determines if they're going to truly enjoy that job or not, which means we have a whole lot of power in being able to create the kind of environment that people look forward to showing up to on a Monday morning. But it's hard to look in the mirror. It's hard to take accountability. I think that's a great, great, great position or a great attitude for managers to take.

Yeah. Do I want to create the kind of environment that people, People want to show up and be in this space on a Monday morning. Yeah. Yeah. Yeah. Because if they do that, well, now they're active. They're being very intentional about the culture.

But it starts with them. It starts with the mirror. In fact, when we did our research, we asked all of our participants, how would you define the word complicated? You mentioned research so many times. Where is all this research? It's on our website. It's in the book. It's there.

We ask all of our participants a very important question. How would you define the word complicated? Because complicated to you might not be complicated to me. And something that's simple to me might be very complicated for you. And so we wanted to get an academic definition of the word complicated. First person wrote this, Leslie. I said, who is Leslie? And what did she do to you?

Like, do you understand the question? The next person wrote the name, Jamal. I said, I know a Jamal. Like, what did Jamal do? And so it's usually a person. Like a lot of times we're looking for, well, is this person difficult? Usually a name pops up in somebody's mind. And we have to come to the sobering reality

that we could be somebody's name. That on the other side of me, Ryan, could be complicated. And if I realize that, well, then I can actually do something about that to go, you know what? I actually want to make this relationship better. And if there's some adjustments that I can make to create the kind of environment that people look forward to showing up to on a Monday, then I want to do that.

Yeah. And it's also, you know, nobody ever labels themselves. I remember talking to a designer once who was just one of the most complicated people on earth. And she was like, I think I'm the nicest person. You do? And that's the funny thing, is you could be easy to work with and a headache at home. You could be a nightmare to raise kids with and the best boss ever. You could be a gym to leadership, but you could be a micromanager to everybody that reports to you.

Like, that's why it's complicated because it really is subjective and in the eye of the beholder. I think that's why this book is so important. I think everybody who is actually working should get this book, and this is a good book to leave with the person who is complicated. Just leave it on their desk with a little love note. That's right. Amber posts often on social media about complicated people at work. Let's watch this short video from Amber.

There are way too many companies and bosses that don't take bullying and abuse at work seriously. And we've all talked about quiet quitting, but I would like to coin the term quiet bullying. There ever been a time where you applied for a job and you were super overqualified, but it's a job that you actually wanted and they turned your way because you were overqualified. The problem is when we're high performers under a bad boss, it makes us look bad if we tell on them, if we go to anybody above them and you just can't really tell anyone. Is it that the biggest bullies at work and the meanest people get moved up into leadership the fastest? Why are they getting the most promotions and the most money?

Too often we hear that people just don't want to work, especially young people. But can we finally talk about the fact that that's true? Some people at your job really, really need to hear this. You are only as beautiful as you treat the people around you. All right. I agree with that. Amber joins us from Virginia. Hi, Amber. I know you've read Ryan's work.

What do you want to ask him? Thank you. Hi, Ryan. Hi, Oprah. Thank you for having me today. It is so cool to be here with you guys. Ryan, I'm a huge fan of yours and something that I really love about what you do is you are incredibly vulnerable. And you don't see that in a lot of professional speakers.

You are really open about talking about your missteps or maybe where you could have done something differently. So a couple of things that really resonated with me about the book because I loved it was this sentiment that we are all weird and irritating and complicated to someone. And when we're difficult, we really expect acceptance and grace. But when someone else is, we just cancel them. So that leads me to my question for you, which is when we're doing all of that inner work. Yeah. And we are dealing with someone that is just, they are just too complicated. What are the signs of that?

What is the sign that they are just too complicated and it's just dead growth at that point? It's a phenomenal question. you know, the subtitle of this book, Strategies for Effective Collaboration with Nearly Anyone. We say nearly because some people are certified crazy and you cannot work with everybody. And so we're hopeful, but we also have to be realistic. I love it. And so there are going to be some people that are unapproachable, uncoachable, unapologetic. And some people just aren't trying to grow. They have this thing in them that says, my personality is crock-potted into what it is.

I'm going to do me, you do, you, boo-boo, is their mantra. And some people just aren't trying to be civil. They're not trying to grill their relationships. They're not trying to be a better colleague. They're not trying to be a better parent, a better spouse. And those are going to be very, very difficult people that you are going to have to have boundaries with. I'm a firm believer that boundaries are not walls.

They are doors with locks on them. which means you decide who comes in and out when you want them to. And a lot of people find that very... That's really good. They find it difficult. They find it difficult to put up boundaries because it shatters the illusion that everybody's my friend. Ah. We want this idea of like, I like everybody and everybody likes me.

That's just not true. That's not reality. And so we do have to put up these boundaries to be able to say, hey, I, I, I, I, I, I can't be close with everybody. I can't be everybody's best friend. I'm not always going to say the right thing. I'm not always going to say everything that you like. And it's okay to pray for somebody from a distance and not be in the group chat anymore.

It's okay to have empathy for somebody and also have some distance. Yeah, Maya Angelou, you mentioned her earlier. My mentor friend used to say, I wish you well and you struggle. I wish you well and you struggle. No question. Yeah, but I'm done with that. Yeah. But I wish you well in your struggle.

And it's okay to do that. I wish you well. Yeah. Really, truly. Every time that you, we are consistently training people how to treat us. And we don't even realize it. Every time that you respond to a text at midnight, you're telling them, it's okay to text me at midnight. Every time you let a comment slide, you're telling them.

Sorry, Tara. You're telling them it's okay. And so it's okay until you tell them that it's not. Yeah. And that's where I believe it's important to set those boundaries. Tara, you can tell me. Tara's been my producer for 30 years. You can tell me.

I just woke up and I had to pee in the middle of the night and I just sent the text or email at that moment. You don't have to answer it. I mean, but this is Oprah. Oprah's different, though. Oprah's different. If Oprah texts me at midnight, I'm responding. Okay, that's different.

No, no, no, no. I just have that thing. And sometimes I'm like, maybe I should just wait. Maybe I should just wait. but okay, so she didn't have to read it. Read it when you want to read it. But anyway, all right. So anything else you want to share with us?

How do we convince people who just assume they're not complicated to actually pick up your book? Because the ones that are that want to do the inner work, like, you know, they're like, yes. That's a really good point, Amber. All of us who are trying to work with the complicated people excluding ourselves, we're picking up the book. But the really complicated people. They're not reading the book. Yeah. Yeah, you know, a counselor friend said this to me a couple of months ago,

and it was just very helpful. She said, don't work harder than your client. Don't work harder than your client. Like, I'm not chasing you to go, hey, when's your next appointment? Hey, when are you going to work on you? No, I'm just going to work on me. My mindset is if my plan in life is to say, my marriage would be better if my wife just got it together. If that's the plan, then the marriage isn't going to get better.

No, no, no. The marriage gets better when I get better. And I grow. And your question is a question that I get all the time. And I just always tell them they're not in the room. You are. And if you're in the room, this book is not about how to fix other people. It's about how to grow you.

And so when you get better, every relationship you have will get better because you've got a growth mindset. You can try and inspire them. You could share some of my videos on social media and say, hey, you should check out this guy. Isn't this guy awesome? I mean, you could do that. And then who knows they'll run into a QR code and they'll buy a book. But I think that the best thing that you can do for somebody that's complicated in your world is for you to grow you and for them to see the fruit of what's happening in your life. Yeah.

Tell yourself a different story maybe. Yes. Yeah, for sure. Yeah. Absolutely. Thank you, Amber. Thanks, Amber. Thank you.

Thank you. I love all your videos, girl. Love those videos. Great work. Thank you. So you share, Ryan. that there's one word to really sum up of, you know, most of your research. And what is that?

Hope. Hope. Okay. Yeah. Hope. You know, there are so many people who feel so stuck in their life. They feel like they have been handed a code of conduct and that they have no other options. The thing I hear from people the most is it's like they're getting their code of conduct from their zip code and their household.

and they talk like this. I'm from Chicago. You're like, hey, calm down. I know some very nice people in Chicago. You know, I'm from Detroit. You're like, hey, Detroit's coming up. Leave Detroit alone, you know? But they have this like, where I'm from indicates where I'm going.

And what sums up this book is, hey, you can be different if you want to. There's hope that if you need to go have that difficult conversation, you can. If you're trying to rebound from a divorce, you can. There is a better future for you. You can decide your code. you can change. That is the purpose of this book. Because, as you say, on the back of the book,

on the other side of complicated, is the wonderful, wide open world of effective collaboration and a workplace you can love. That's right. Especially if managers are thinking about how do I make this the kind of workplace that people want to come to on a Monday?

I think so. So many really vital lessons in this book. Thank you for writing it. Ryan Leak. And our thanks to Brian and Nadia and Amber, Ryan's book, how to work with complicated people is available everywhere books are sold. I know you know somebody who needs this book.

Go well. Thank you so much. And thank you to our friends at Geico for presenting today's episode. If you've ever struggled with a difficult boss or co-worker, and really who hasn't, the QR code for Ryan Leake's book, How to Work with Complicated People, is on your screen. And it may be exactly what you need. It's a guide to understanding others more deeply, communicating more effectively yourself

and finding better ways to work through conflict. You can buy it right this second just by scanning the QR code on your screen. Here's to better relationships. Our listeners tell us that the podcast is resonating with you and is serving as a bright spot in your day. That means a lot to me. So here's the thing.

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