How to Work with Anyone Even the Difficult Ones with Ryan Leak

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1:16this is the admiral show welcome back to the show everybody okay interesting anecdote a friend of ours a mutual friend of my guest today said hey i've got ryan leak that wants to come on your show puts us on a group text i said, Ryan, I know who you are. Let's do an interview. This friend is Rory Vaden. Yes. Then he sends me the book and it's not the same Ryan leak after I agreed to do the interview. But then I read the book. I'm open. I read the book. I go, Oh no, no, no. I definitely want this guy on the show. So actually the content of your work is so good. I'm like, Oh no, this needs to be discussed because it's a topic, which we're going to talk about next that's under discussed and is a massive issue in people's lives.

1:58They don't know how to navigate it. So this Ryan leak no offense to the other one my upgraded guest today has a book called how to work with complicated people and i got to tell you something i want to know a lot of this stuff so i read the book from the cover to the end of it wow every word of it took me three days thank you and it really changed my life he's uh he's worked with everybody from the nfl you guys google microsoft and so once i figured out who this ryan leak was i told him also off camera everybody i know that knows him raves about him and tells me this is going to be an incredible conversation today.

2:30So the real Ryan Leak, welcome to the show. Thanks, it is a pleasure to be here. It's so good to have you. So this is perfect segue since I blew it. One of the quotes from the book, I'm like, this will be perfect, is you're somebody's idiot. And I'm like, I clearly represent that, but it's one of the principles of working with complicated people. So let's just start there because I'm a perfect description of somebody's idiot. so tell us about what that means you know it's this idea that we could live in a world where we think man this person's an idiot and it's just like we have but we're always somebody's person that is that person and so anytime i tell people hey i'm working on a book called how to work with complicated people they go yeah i need that book and then i go hey spoiler alert somebody needs that book for you and somebody needs that book for me it's interesting we hear this phrase a lot toxic work environment or I've got a toxic boss.

3:23The problem with that word is no one admits that they are that. We've never met someone say, hey man, I'm going through a lot in my life right now and I'm toxic. People just don't admit that kind of thing. And so it's a word that it's like 72 % of America would describe their work environment as toxic. It's just thrown out there a lot, but nobody wants to admit that they're that. And so I think that idea that we're all somebody's idiot, it just postures us with a little bit of humility to say, Hey man, you know what? Maybe on the other side of me, it's a little bit more. You know, I never thought about it that way, but when I read that in the book, I'm like, Oh, I, I can definitely name several hundred people in my life after 54 years of like that dude's an idiot.

4:04And by the way, there's some great videos that helped me on social media where I say cavemen lived 300 years ago. I misspoke. So I'm literally 300 million people's idiot most of the time. So that's just the way it goes. But also what I like about the book, everyone's lean in here is if you actually, and we're going going to talk about this today. It's work, but it's also family too. It's basically just interpersonal relationships and how to navigate complicated. So if you go, I don't have a complicated work environment, but my spouse or my children or my mom is, or my mother-in-law is, or my father-in-law is, we got some stuff for you today.

4:33So is that what made you write the book? Is something in your own life or environment that happened? So I do about 120 events a year and I always do a pre-event call with every single client. And I ask the same questions. Hey, what are the biggest challenges your people are facing right now? What we discovered was that most people's biggest hurdle to job satisfaction was not their job description. It was the people that they had to do the job with. So you actually can pull off a very difficult job with people you enjoy versus a dream job with people you tolerate. And so we said, man, if we can help people figure out the people side of it, man, it'll make their job a whole lot better.

5:12Yeah. You know, my issue was maybe still is a little bit but I didn't realize it till after about 25 years of being in business I liked people like me and so if they weren't like me like I as a young guy you know overly competitive incredibly intense very verbal right very no nonsense so if you didn't have that criteria former athlete so if you didn't have that you were an idiot yeah you know I mean I'm using your word. I don't think I felt like that strong, but like, like certainly didn't think they were great workers. And then what I realized after some time was like, actually I already have me.

5:48So I don't really need that many more means. I need people that have all the stuff I don't have, but is that part of our biases or this toxicity in this complicated environment as we seem to only feel ours have an affection or an affinity for people like us? Yeah. I think we all desire sameness. We desire to have that tribe around us that think the same ways, that have all of the same values, but it's not until you have somebody on your team that's a little bit different, that sees the world from a little bit of a different perspective, that we can sell to people that have a little bit of a different perspective.

6:21They're all bringing something to the table. Doesn't mean you just hire anybody. Most people, they have to work with the people. They don't get to choose unless you're the boss, unless you're the CEO. Most people are like, dude, I'm stuck with Jerry. So what am I going to do with Jerry? So we just try to help people where they're at and say, hey, if you can figure out how to work with this person that and sees the world completely different than you, well, then maybe you could lead some people that are completely different than you. So you're practicing for your new job at your current job by developing some of these people skills.

6:51How do you do it? Like it was a couple of things. Well, one of the things I think you have to do is you have to remain curious. You have to remain curious. You have to go. I mean, there's a way that I think work should be done. There's a pace in which I have my I'm very fast paced, very high energy, very intense, like let's move well when all of a sudden i started to realize well i got some people in my team that are a little bit slower and i'm just like hey could you could you pick up the pace but then i realized i was actually making mistakes going so fast yeah good point and they were actually being very detail oriented and so there i found a blessing in their pace to be able to say you know what maybe maybe there's a balance here i need to be a little bit more considerate of their pace versus my pace.

7:35I think having that posture of curiosity is very important. What about understanding? So this is conversations happening on a fascinating day for me. So I have multiple businesses. I guess the podcast is a business, right? But in between interviews, Stephen will tell you, my producer, I had to go upstairs and take a call. I've had a very stressful morning dealing with a employee of mine in one of my businesses that I would say is a complicated person. And in this particular person's case, whom I love, it is a him, but I have enough business. I don't know what I'm talking about. It's a him, but about every three weeks or four weeks, I'm on an emotional roller coaster where this dude is on his way out.

8:12I mean, he's just, he's complicated. I also know he may have a proclivity to the melancholy side of life, if that makes sense, the negative a little bit, right? The negative. And so today I've been dealing with him and it came to a head again, I'm going to quit. Okay, you're quitting out and then now he's not. And so how do you deal or your perspective on just, and by the way, this could be family. So this could be business or complicated people. And, and also I'll give you the double and you know, some other patterns by now. Yeah. Do you know what I'm talking about? Absolutely. Okay. I think it's very important that you do two things.

8:48One, I think we've lost the art of having difficult conversations. Our friend, John Maxwell says it this way. We have to learn to disagree without disrespect. It's the art of just saying, hey, let's have this conversation. I think being able to go to somebody, family member, co-worker, boss, and being able to say these words, hey, I want to have a thriving relationship with you. I want this to work out. Sometimes what happens is we're almost dealing with the symptoms instead of the root issues. We're not actually talking. We're going, hey, could you rewrite that email? Hey, can you not do that on that project?

9:26It's like, wait, let's just let's actually talk about the elephant in the room. Let's actually have that direct, truthful conversation and say, hey, for us to have a thriving, working relationship, here's what needs to change. Hey, here's the part that what do you think I need to do for us to have a thriving relationship? So I'm coming into it with some humility. It's not all on you. You're not just the whole problem. But I'm going, what is it that you need from me for this to be a thriving relationship? and here's what I need from you. And if we can't meet in the middle, the key word on the book is strategies for effective collaboration with nearly anyone.

10:01Sometimes they're in the nearly and sometimes they don't make the cut. But I think we want to do everything in our part to say, hey, I did everything in my part to make this work. You know why that's brilliant? I kind of almost grunted when he said it because what starts to happen when there's strife, correct me if you you think I'm wrong, but we forget or aren't reminded of each other's intent. Intentions get lost in stress. And so what you just said that's so powerful there is to start out with, look, my intention, I want this to work out with the two of us. I want this to be thriving. I want you to be happy.

10:34I want you, I did do that today with this person, so I feel good about it, which is true. But I thought I need to be the emotionally mature one to sort of rise above the emotion to some extent yes you know the other truth with this person i need them in other words they are complicated but they are uniquely gifted and talented they are the juice is worth the squeeze in other words there's a squeeze yeah but it's worth it and so one of the things you say in the book and this is true even in friends too the avoidance of difficult conversations or the avoidance of having people like this in our business life is really to our detriment well Well, I think even in your specific situation, you've got two options.

11:15You have the options of having two headaches. You either have the headache of dealing with their personality. Yes. Or you have the headache of retraining somebody to have all of their skill sets. So it's like, choose your headache. And you do have options on that. I think you exhaust the option of the personality to say, hey, I want to do everything in my power to work this out before I go choose that second headache. Yeah. So, but it is a realization of saying, is there something that I can be doing to help you be more effective in this job? Specifically with our relationship, you keep bringing this thing to the table and we're rehearsing the same old lines.

11:58And so at some point it's just got to be different. But I think being willing to have that difficult conversation, and I love using the phrase, I could be wrong. hey i could be wrong but this is this is what i this is what i see and what you're saying is yeah i got a story in my head about you i really do yeah but i realize i could be wrong about that you're so brilliant i'm this is like serendipitous i texted that to him before the call you know i could be wrong but and about and i actually just meant it like i really could be wrong right like you just said i love highly tactical podcasts like that's a huge thing to start out a conversation somebody say my intentions are blankety blank second tactic that i love this understanding seek to be curious the third tactic that i love is this idea of you know i could be wrong could be some humility absolutely what happens i think don't use with complicated people or maybe we're the idiot like you said like there's just a there's this posturing and flexing that goes on like at the end of the day once they're gone or it's resolved you're like 74 of this was just posturing and flexing and I'm more important than you don't disrespect me like these just yeah ridiculous notions that we do to one another as humans yeah they're games aren't they and I think at some point you stop playing the game yes you just start being a leader you just start being that colleague that just says hey again I think there's something powerful about stating that intention at the beginning of a conversation it changes the tone it changes of the motives of the entire conversation hey i really want this to work out as soon as you say that there is a there's an immediate okay i can actually put my defense down because i actually want this to work out too now if you don't want it to work out well then well now we know where we are yeah you're right i ask i ask a lot of questions you and i were talking about john maxwell off camera and you brought him up here mutual friend of both of ours and i love him and we were together doing something and i said, what's different?

13:57It's the 70, whatever John is 75 or eight. I said, what's the difference of the 78 year old you and the 58 year old you in terms of being a leader? And he goes, oh, I know exactly what it is. He said, the difference is I don't have to be consistent in my thinking all the time anymore. And I said, what do you mean by that? He goes, I'm open to changing my mind. I'm more open to being wrong. He said, when I was in my fifties, I thought if I didn't stick true to what I believed or thought about something, I was being an inconsistent thinker. And he said, now my tolerance for leaders who never say I'm sorry, never change their mind with new information is really frustrating to me.

14:30So actually, I really listen with people that I admire. And so in this particular situation today, I also said, just for a tactic for everybody, I want your feedback on it. I said, the other thing I want to do is I want to apologize to you. because consistently I'm doing something, I mean, where I am not giving you what you need to feel respected and appreciated. As it turns out, it wasn't me at all. It was someone else. But the point is, I think there's also a power to just going, I'm going to be the more humble one, not the flexor, especially when you're in the position of authority already.

15:05Do you agree with that? Like just humility is such a, it pulls the oxygen or the heat out of the environment pretty quickly. No question about it, especially if you're in leadership, because there's an automatic intimidation factor that comes in whenever you're, especially you're trying to have a difficult conversation with a difficult or complicated person. In chapter eight, we talk about all of the different directions of communication and leading. Can you do a little bit of that too? Sure. So what can make a conversation complicated is the direction of the conversation, especially when you are having a conversation up.

15:41You're having the conversation upwards. There's this intimidation factor when you're having the conversation down. Well, there needs to be a high level of humility because, well, we've all had a boss at some point in our life and we just, what's the number one thing that we would say in terms of the relationship that we had with that boss was that we did not feel like we could always be honest. Brilliant. You're right. We always felt, we had a thought and we go, yeah. Yeah. I love it here. It's great. Yeah. No, man. And everything's awesome. We're like, well, everything can't be that awesome. And so you actually have to have a great deal of humility, more humility than they need to be able to lead them well and to actually get real and honest feedback, to be able to say, man, like there's an intimidation factor that just comes with the role that you have.

16:28And so whenever you, whatever direction it is that you're communicating, You have to consider your end of that. If you're talking up, you're going, well, what's important to them? They've got very little time. And I want to make sure that I value their time and not waste it. There's nothing more frustrating for a high level leader than to have their time wasted. And so being succinct, thinking through some of those things beforehand is important. But when you're talking down, you have to realize you are looking up, receiving a message at some point in your life. and you have to go back there and go, man, what did I want to happen?

17:02Oh, boy. In that moment, you wanted somebody to go, hey, man, I see you. I want to share a story with you about exactly what you just said, and I want your feedback on it, but not as a business leader, but as a parent. Yeah. So a few weeks ago, unfortunately, I haven't even put this out on social media yet, but we lost our dog, Lily. Oh, man, I'm sorry. We have three. Yeah, everyone that follows me on social for years know we're very close with our three Pomeranians. And so Lily was the matriarch. We lost her. Excuse me. Wow. And my daughter's home. It was my daughter. I gave my daughter her. That was her gift as a dog.

17:37My daughter happened to be home from college when it happened. Anyway, it was an emotional thing. And as she was passing, there was these discussions of how many times are going to take her to the vet. She was in the hospital for five days. It just got emotionally charged. So just picture an emotionally charged conversation. And my daughter observed my communication with my wife and hers with me. And in the middle of it, my daughter, let's just say, sided with the way her mom was communicating and not me. And came to me with firm feedback. We'll put it that way. And I would actually say that's how it was.

18:13I wouldn't even say I'm wordsmithing. And in that moment, I had two choices, which was one to flex. I'm the father. You know that thing. Oh, yeah. Or to be humble and truly listen to my daughter. Yeah. And in that moment, I said, you know what? You're right. Yeah. You're right. And I'm going to do what you just suggest. This is from my daughter. Yeah. And I could have said, I paid the bills around here. Then my daughter went to bed and I went into her. I knocked on her door and I said, can I come in for a minute? And I said, I just want you to know how right you were. And I apologize. And I thought, hey, right in this last hour, I've been a pretty good dad, a pretty good leader.

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20:48so one is the humility piece the second thing when i look back on leaders that i've worked with or for that i admire i feel like they really listened to me well and asked questions whereas the other ones talked at me yep so how much of this because i listened to her how much of this is creating a sense with complicated people that you're exact you're actually listening to them How big of an element do you think that is? I think it's massive. Because if you walk into a room and you're simply dictating what everyone should do and say, hey, go make my ideas happen, you have robots. But if you walk into a room and go, let me pull out the gold inside of you, then we all create something together.

21:34Now you have a team. You're right. But you had to have listened to everybody to be able to pull that off. That is the difference to me between somebody that is leading and people have to follow them and leading and people get to follow. Yeah, they lead by position. They don't lead by their actual standing. It's interesting because especially when people come to work with me because I whatever they'll think as a public person and a guru or like, oh, he must think he has all the answers. And they're usually very surprised. And I go, I actually have to go out of my life to go listen to me. I really want to know what you think.

22:09yeah okay like i know what i think absolutely there's no more space for what i think i want to know what you think and i think that sends a message to people you are valued and you're appreciated you have the book i just want you to give them this gift because there's so much in the book you could give away anything i ask you it's to be good but you have basically the four responses yeah that you teach in the book to complicated people to have kind of avoid right so here's what's not to do and i love these because you're right on all of them yeah what are those? So the first thing that you could do with a complicated person is you can avoid them, which a lot of people just try to say, Hey, let me just, let me just do my best to avoid talking to this person instead of meetings with them, which again, you don't buy books to avoid people.

22:51Like nobody does that. You're already good at that. So you don't need my help with that. And while you can do that, I don't think that's the growing version of you. I think there's a better option. The other option is you could cancel them. You could just say, you know, I'm done with this person altogether. I mean, you could, but the only problem is none of us like being on the other end of being canceled. The other option is you could try and change them. Right. And it's just like that lives with the mantra that says the world would be a better place if you were just like me. Yes. And the world wouldn't be a better place.

23:22You think the echo chamber is what you need, but that's not how you grow either. Again, you can try it. You're grown. You can do whatever you want. But the fourth option that we tell people to do in the book, which is like the hope of the book completely, which is to try to move towards someone with understanding because every single one of us has had a moment where we were misunderstood. And in that moment, we were thinking, oh, wait, wait, wait, wait, wait, wait, no, no, no. You misread it. No, that wasn't my tone. I know I texted it, but that wasn't the tone in which I used. And like, in that moment, we all want our day in court.

23:51But when it's somebody else, it's like, well, we want karma for them and grace for ourselves. And so when we have this posture of saying, you know what, I want to move towards this person with understanding, what we discover is that complicated people often have a complicated behind the scenes. And when we begin to see what they were going through, when we begin to see, oh, wait, they lost their dog. Oh, wait, he had a very emotionally charged conversation with his daughter last night. And now he's having one with me. And I, but I didn't know that. But once I know that I go, oh, the conversation changed, even though the words were the same, the understanding postured me completely different.

24:30And so I think when we are the kinds of people that make a decision. He says, man, I'm not going to jump to conclusions about people because I hate when people do it to me. I actually want to be slow to talk, quick to listen, and be one of those people that go, man, I'm sure there might be more going on behind the scenes than I could ever see. I send out a text. It's an encouraging text to thousands of people every single week. One week I sent out the text. I said, hey, is there anything going on in your life that I can pray for. I'm a person of faith. I said, man, let's just see what's going on with people in the world.

25:03This isn't a church group. These are all corporate people that I'm texting. I got 3 ,000 responses in one hour. Whoa. And my phone blew up. Whoa. With insanity. And my first thought was, I guarantee you, their boss doesn't know. You're so right, brother. And they're just going to go to work. I sent that out on a Monday and guess what they're going to do? They're going to go to work on a Tuesday. And so I often tell people, I say, Hey, the people you work with, they're going through something they would never tell you. They say, how do you know? I could show you my phone. Unbelievable. And so if you knew what they were going through, you would go, man, let me give them a pass.

25:43Little grace. Because it's what you and I both want. Yes. It's just that we have to get in that position of being the kinds of people that give that thing that we want the most. I'm loving this just so you know. I wonder if part of it is we talk a lot in personal, like our own biases or our own worldview. I also think when someone's been in your life a while, you think you know who they are. So you're like, okay, that's the victim one. That's the one who gets set off really easy about this. That's the emotional one. That's the one who really doesn't care as much as everybody else. That's the lazy one.