How to Work with Difficult People (Without Losing Yourself)

0:00This 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.

0:42I 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.

1:23And 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 a bestselling 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.

2:14It 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.

2:59Number 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. We all, 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.

3:38And 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?

4:10And 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 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.

4:43So when I saw this title, How to Work with Complicated People, 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.

5:23And 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 used, Ryan, the word complicated. complicated. You could have said 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.

5:58They would 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 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.

6:43And 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? 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, But 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.

7:17They 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.

7:57Yeah. 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 complications. Yeah, 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. Okay? As much as you try. You can do everything in your power to try and avoid.

8:28You 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 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, yeah.

8:56Like, it's, 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 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 every year. And one year, because people used to come up to me and say, oh, I watched this show.

9:27It 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.

9:59Well, 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. 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.

10:36In 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.

11:07And 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.

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12:20And when people share their stories, we're reminded that we're not alone in this journey called life. As the official insurance partner of the podcast, the folks at Geico 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.

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13:13You 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 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 doesn't match our inner definition of what is right or normal.

14:03and 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.

14:40I 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 actually see complicated coming a mile away. In fact, it's like you've worked with these people for a very, very long time.

15:15You've been married to this person. You've dated this person for a long time. 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.

16:02And 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 and perfect, except nobody's that.

16:47In 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, 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.

17:22You get that email. That's right. And sends you over the edge or you get a certain look from your boss or colleague 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.

18:00Because 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. So shouldn't you in that moment say, what just happened here? 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?

18:31Oh, 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? Absolutely. I feel humiliated or I feel embarrassed or I feel, you know. I feel shame. I feel shame. Yep. Those are the questions you should be asking yourself. Absolutely. Yeah. 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 business?

19:05I'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. 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.

19:43And realize they're happy. They've 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 7.18 a.m. And now is 4.33 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. 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 with you first when that trigger yep first was implanted for sure the back of your brain absolutely yeah and whatever that thing is and it happens to me all the time you know my i turned nine years old really fast because when i was nine years old my father unfortunately suffered a stroke.

20:42Our 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. 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.

21:22I immediately go back to I don't need nobody. But I do need people. Yeah. And so if you're triggered. 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. If you find yourself tripped. 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, 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 just decided, I realize there's some things that happened in my childhood that I wish didn't, but I'm adult right now.

22:03So I can have an adult conversation. Yes. And so people use this now. 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? Because people assume, I think, when I've heard people use it 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.

22:40Brian 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.

23:18That'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 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, 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.

23:55And 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.

24:44The 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-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 the 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.