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How to Work with Difficult People (Without Losing Yourself)

49m 22s

How to Work with Difficult People (Without Losing Yourself)

This episode features Ryan Leak, author of *How to Work with Complicated People*, who argues that most workplace conflicts are rooted in personal expectations rather than inherent flaws in others. The central idea is that people are often "complicated" because their behaviors, communication styles, or values differ from our own, not because they are malicious. Leak introduces the concept of an "expectations detox," encouraging listeners to question what they expect from coworkers—such as identical priorities or perfect behavior—and to stop reacting with shock when those expectations aren’t met. He emphasizes that understanding others with curiosity, rather than judgment, leads to better collaboration and personal growth. Key strategies include setting one’s own attitude as a leader, establishing healthy boundaries, and recognizing that most conflict stems from misaligned expectations. The book also highlights the importance of self-awareness—when we grow personally, our relationships improve. Ultimately, Leak promotes a hopeful, collaborative mindset, showing that even in difficult workplaces, effective relationships and job satisfaction are possible through intentional self-reflection and empathy. The message is clear: the journey to better work life begins not with fixing others, but with transforming oneself.

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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. 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 Leak is a sought-after speaker. 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? That's right. And even if you think. 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? 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. 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 incivility. Disrespect, disregard. Oh, name calling. Vitriol. Yeah, just it turned into it turns into a thing. A hundred percent. 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. Well, 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 life at work. 90,000 hours of your life is going to be at work. And what determines if somebody loves. Loves or enjoys their job is not often the job description. 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. And 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 and 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. It's 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. And I like the fact that you use, Ryan, the word complicated. You could have said assholes, how to work with assholes, how to work with jerks. Yeah. 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 would say, well, they're not, they're not bad. They're, well, they're complicated. And so it was somebody that was, 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. 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. 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. 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 when we, 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. Yeah. 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, I can be intimidating and I know all those things. Yeah. But I just. 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 you, we all have, we all have different strategies for how we're going to do. 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, I've found that complicated people are unavoidable. Yes. Okay. As much as you try. You can do everything in your power. You can't run into them. You have to deal with them. They will find you. They will find you. Okay. 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, if somebody walked up to you and said, Hey, I'm really looking forward to changing you soon. You'd be like, what? You're not changing me. Yeah. Like it's, it's nobody even really wants to change you. Nobody wants to be changed, but they also want to try and 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 do a better job the next year than we did before. I never considered anybody else competition. We were competing with ourselves. Yeah. And one year, and we would have themes for every year and one year because people used to come up to me and say, Oh, I watched the show. It changed my life. It changed my life. It changed my life. This show changed my life. You 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 changed 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. Yes. It's a terrible mantra to live by. Yes. And you can 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 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. 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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 live. With insurance designed 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 inner self. I'm working with them. 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 collaboration 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. It doesn't match our inner definition of what is right or normal. 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? 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. 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 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. Well, and I think that works in the opposite, 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 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. 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, imperfect, except nobody is 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, I'll 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, hmm, somebody needs that book for me. Yeah. That is true. I think that's where the growth 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 a 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. You should really name what's happening. Because when you give a name to 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. Oh, most people are going to say, oh, 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? I feel humiliated or I feel embarrassed or I feel, you know. 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 week? Yeah. 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 day? I'm sure I'm not going to let Keith. He's behind the camera. 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. Living life. Living life. Turned, went into the Tiffany store. The Tiffany store. Spending money. Spending money. And I'm, like, I'm walking around here mad. That's right. Thinking that person's also walking around mad, feeling my whatever, whatever. And realize they're happy. They're gone on with their lives. That's right. 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. Sure. 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 pocky book. That's right. Going into Tiffany's. Yeah, they're not thinking about you. They're not thinking about you. 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-olds. 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, I turned 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. I don't, if a client starts talking crazy to me, I'll go, I don't need to be here. I, I, 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, if you're triggered. That's what I'm saying. That, that, that right there, Ryan, that's going to help a lot of people. That's going to help a lot of people. Yeah. I, I would just encourage people. If you find yourself triggered. That specific example is going to help a lot of people. Cause 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've, be the adult 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, you've just decided. I realize there's some things that happened in my childhood that I wish didn't, but I'm adult right now, so I can have an adult conversation. Yes. And so people use this now that trigger has become the word. I just got triggered. I just got triggered, but not willing to examine what does that really mean? Cause people, people assume, I think what 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. 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 and Brian is joining us. Hi, Brian. Sup Brian. From the class trip to Washington, DC, the classic eighth grade trip to DC. 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. Been through the capital 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 and I'm. 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 the few teachers in my twenties. The other four are. The only others in their twenties. 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 arrogance. 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-some, 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 is 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. 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 a know-it-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 am I, what are you unlearning? What you're showing is a great honor and respect for them, but you're also getting their wheel 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, and it's 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-some, I think it's really going to help you add value to it. You know, I had Simon Sinek here at the Tea 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 this on the same front 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 didn't pay off so well. They've just seen so many things that prior generations didn't experience. I mean, all the kids you're teaching have grown up from birth with technology, cell phones and all of that, which makes a very different world and world experience. And I think what Brian 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, so how do you think it's different? And do you think it's different? 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, is to see it differently and to bring them along without offending them, without like, y'all are old, without saying y'all are old. I think that absolutely, it makes sense to me. I mean, it has been just so rewarding to do that full. I mean, I think it's a wonderful 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, I think these are some good takeaways, right? Yeah, absolutely. I mean, we are already looking forward to next year, but we're coming to the end of chapter one and I really just want to start utilizing some of these approaches for hopefully a long and successful career with my kids. I think that's great. Yeah, I love it. I love teachers. Thank you. Thank you so much, Brian. Thank you. Love you, Brian. Appreciate you. Thank you, Brian. So you devote a whole entire chapter to communication, right? Right. Yeah. And you've concluded what? That most people are pretty flawed at communicating. Yeah. And that's the word everybody always use. We just need better communication. Yeah. Yeah. We just need to have better communication. So how, how do 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? I think that's, I think, 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 maybe 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 if we're honest about what our actual goal is with these conversations, it's actually agreement. I actually have something in low key. I actually really want you to agree with me. And so that is, 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. 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. Yeah. 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, right? 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 conversation leading complicated teams. And let's, let's unpack that a bit. It could be, they are not intentionally complicated. It could be macro, micro things, org changes, difficult economy. Yeah. 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, you've got quite a few layers there. And Juan, thank you for your vulnerability and even just being able to come on the show. I think part of it is, 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. I'm not going to do that. 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'm not going to do that. What 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, but 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 icebreakers. 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. Okay. They mad at the weather. They mad at the gate agent. They mad at TSA. They mad at everybody. And so I'm just, made a decision that since this is where I work, I'm not going to be mad. What? I'm expecting it to not go well. I'm expecting the delay. I'm expecting weather 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. 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 light 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 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? 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 the time. Or you get them in text and so forth. Oh, yeah. 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. Thank you. Thank you, Nadia. You're welcome. Oh, yeah. Big time. Yeah. It's amazing. It's just a little. The under half have skipped a day of 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 and to go, man. 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 want to show up and be in this space on a Monday morning? Yeah. Yeah. Because if they do that, well, now they're active. They're being very intentional about the culture. Sure. 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've mentioned research so many times. Where is all this research? Yes. It's on our website. It's in the book. It's there. We asked 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. Right. 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. Who is Leslie? I said, who is Leslie? And what did she do to you? Like, do you understand the question? 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'm going to be complicated. Yeah. 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 complicated. You know, 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? Well, and that's the funny thing is, 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 gem 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, but 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 background, 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 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. 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 reading it. It's a book about how people are so intimate that we are all weird and irritating and complicated to someone. And when we are 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 and we are dealing with someone that is just they are just too complicated and it's just dead growth at that point. It's a phenomenal question. 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. And so there are going to be some people that are unapproachable, uncoachable, and some people just aren't trying to grow. They have this thing in them that says my personality is crockpotted 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 grow 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 good. They find it difficult to put up boundaries because it shatters the illusion that everybody's my friend. We want this idea of like, I like everybody and everybody likes me. That's just not true. That's not true. That's not reality. And so we do have to put up these boundaries to be able to say, hey, 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 in your struggle. I wish you well in your struggle. No question. Yeah. But I'm done with that. But I wish you well in your struggle. And it's okay to do that. I wish you well. 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. Okay. 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. 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 a 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, no. I just have that thing. And sometimes- 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, they're like, yes, you're going to 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, I, 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, I'm just going to work on me. My mindset is, if, 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 I'm going to work harder. I'm going to work harder. Then the marriage isn't going to get better. No, no, no. The marriage gets better when I get better. When I grow, when I, so, 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 if you, when you get better, every relationship you have will get better because you've, 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, and then who knows, they'll run into a QR code and they'll, 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. Really tell yourself a different story. Maybe. Yeah. Yes. Yeah, for sure. Yeah. Yeah. Absolutely. Thank you, Amber. Thank you. Thank you guys. Love all your videos, girl. Love those videos. Thank you. So you share, Ryan, that there's one word to really sum up, 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, 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. Yeah. 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 load, 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 Leak'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 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. So here's the thing. I would really appreciate it if you like and subscribe to the podcast. It's just a quick tap of the subscribe button. And that way you won't miss an episode in your queue. I know subscribe usually means you're paying something. But this time it means you just are notified when there's something new. So thank you for watching and listening.

Podcast Summary

Key Points:

  1. Nearly half of Americans quit their jobs due to issues with their boss, highlighting that workplace relationships, not job descriptions, determine job satisfaction.
  2. The book introduces an "expectations detox," encouraging listeners to question their own expectations of others and reduce reactivity to perceived flaws.
  3. Complicated people are not inherently bad—they often reflect differences in communication styles, values, or experiences, and the root issue is usually misalignment in expectations, not malice.
  4. The most effective strategy for dealing with difficult people is to understand them with curiosity instead of judgment, which fosters connection and mutual growth.
  5. Attitude, not personality or politics, is the number one factor in whether someone is enjoyable to work with, and leaders can set a positive tone that is contagious.
  6. Boundaries are not walls but doors with locks—allowing people to enter or exit relationships based on mutual respect and self-awareness.
  7. The core message is that growth begins with self-reflection; improving personal awareness leads to better relationships and workplaces.
  8. The book emphasizes hope—offering a pathway for personal and professional transformation through collaboration rather than conflict.

Summary:

This episode features Ryan Leak, author of *How to Work with Complicated People*, who argues that most workplace conflicts are rooted in personal expectations rather than inherent flaws in others. The central idea is that people are often "complicated" because their behaviors, communication styles, or values differ from our own, not because they are malicious. Leak introduces the concept of an "expectations detox," encouraging listeners to question what they expect from coworkers—such as identical priorities or perfect behavior—and to stop reacting with shock when those expectations aren’t met.

He emphasizes that understanding others with curiosity, rather than judgment, leads to better collaboration and personal growth. Key strategies include setting one’s own attitude as a leader, establishing healthy boundaries, and recognizing that most conflict stems from misaligned expectations. The book also highlights the importance of self-awareness—when we grow personally, our relationships improve.

Ultimately, Leak promotes a hopeful, collaborative mindset, showing that even in difficult workplaces, effective relationships and job satisfaction are possible through intentional self-reflection and empathy. The message is clear: the journey to better work life begins not with fixing others, but with transforming oneself.

FAQs

Nearly half of Americans quit their jobs because of their boss. The relationship with leadership significantly impacts job satisfaction, as work-related problems are often rooted in interpersonal dynamics rather than job responsibilities.

An expectations detox involves questioning what you expect from others—like identical priorities or instant changes. It helps reduce frustration by recognizing that people are often complicated and not meeting your idealized standards, allowing for more understanding and patience.

Self-reflection reveals that we all have behaviors or quirks that others find complicated. By acknowledging your own role in difficult interactions, you gain empathy, reduce blame, and build a foundation for more collaborative relationships.

The four strategies are avoid, change, cancel, and understand. The most effective is 'understand,' as it fosters curiosity and connection. This leads to deeper insight into the other person’s perspective and often reduces conflict over time.

Setting the standard means choosing your own attitude and energy, especially in stressful situations. Instead of matching someone else’s negative emotions, you maintain a positive, grounded presence, which influences the overall tone of interactions.

The word 'complicated' reflects research showing that people are not inherently bad—they simply have different values, styles, or behaviors. This title emphasizes collaboration and understanding over judgment or confrontation.

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