Executive Podcast #334: How to Work with Complicated People feat. Ryan Leak

Chris Goede and Perry Holley unpack the challenges of leading in all directions and working with complex personalities. Drawing from Ryan Leak’s insights, they explore managing overachievers, partnering with territorial peers, and meeting demanding bosses’ expectations. They emphasize empathy, adaptability, and the power of collaboration, offering practical strategies to build influence and foster strong workplace relationships.
References:
Pre-order Ryan Leak’s book, How to Work with Complicated People (available April 15th)!
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Perry Holley:
Welcome to the Maxwell Leadership Executive Podcast where our goal is to help you increase your reputation as a leader, increase your ability to influence others, and increase your ability to fully engage your team to deliver remarkable results. Hi, I’m Perry Holley, a Maxwell Leadership facilitator and coach.
Chris Goede:
And I’m Chris Goede, executive vice president with Maxwell Leadership. Welcome and thank you for joining listeners. I’m just gonna jump right into this title because I’m super excited about the title today. Cause Perry let me pick it and well, since you guys know a little bit about Perry, I thought I got the perfect title for my partner here and my co host. The topic today is gonna be how to work with Complicated People. And so we’re gonna talk a little bit about Perry. No, I’m just kidding, man. We are so excited about this topic because I think we that at times in our leadership, matter of fact, some may be around the table right now listening to this and thinking about people that are sitting with them that may be complicated, but it’s a real thing.
Chris Goede:
And we’re not going to always have easy people to deal with and so how to work with complicated people. But here’s a surprise for you guys. Maxwell Leadership Publishing is about to release a brand new book with our partnership with Ryan Leak called How to Work with Complicated People. So we have a surprise for you. You’re in for a treat today. You’re going to be the very first to get a sneak peek directly from Ryan about some content on this book. And then Perry and I are going to spend a little bit of time unpacking it. We’re going to dive a little bit deeper into lessons.
Chris Goede:
We’ll talk about some practical ways we’ve seen some of our partners do it in the field and maybe some of our experience through our journey. But let me stop real quick before you listen to Ryan. If you want to pre order the book while you’re even listening to the lesson, just make sure you come back to the part that Perry and I want to unpack for you. Just scroll down to the show notes. Okay. And in there, if you’ll click on the link because that’s where you’ll be able to pre order the book. I know Perry myself have had the chance to look at that content and this is so relevant. We’re super excited for you to be a part of it.
Chris Goede:
All right, here’s Ryan Leak.
Ryan Leak:
Module number one. The complexity of leading in all directions. Here’s the thing about leadership. It’s not like building IKEA furniture where there’s A step by step manual. Even if you still mess that up. Sometimes leadership is like putting together IKEA furniture without instructions with half the parts missing, while three people yell at you about how you’re doing it wrong. It’s complex because people are complex. When you’re leading down, you’re managing people who expect you to have all the answers.
Ryan Leak:
Spoiler alert, you don’t. When you’re leading across, you’re working with peers who sometimes see you as competition, not as a collaborator. And leading up? Well, that’s a whole other beast, because your boss probably has their own blind spots, insecurities, and a to do list longer than a receipt from cbs. In short, every direction of leadership has its own unique challenges. But there’s one thing they all have in common. The need for intentionality. Here’s where preparation matters. Expecting complexity helps you prepare for it.
Ryan Leak:
If you walk into every interaction assuming it will be smooth sailing, you’ll be caught off guard when turbulence hits. But if you acknowledge that leading in all directions comes with layers of difficulty, you can equip yourself with the right mindset and tools. Think of it like packing for a trip. If you know the weather might be unpredictable, you pack layers. Leadership is the same way. When you expect complications, you’re better equipped to handle them. Take this, for example. Imagine you’re managing a team of a bunch of overachievers who keep stepping on each other’s toes, and you need to lead down by setting clear expectations.
Ryan Leak:
Now, at the same time, you’re trying to partner with a peer who’s territorial about their responsibilities. So you’re leading across by finding common ground. And oh, by the way, your boss just complained in a meeting that you’re not being proactive enough. So you’re also leading up by figuring out how to make their life easier. You see what I mean? It’s complex. You’re being pulled in a bunch of different directions, and you’re having to lead from the middle. But here’s the good news. Complexity doesn’t mean chaos.
Ryan Leak:
When you approach leadership with empathy and adaptability, you can navigate even the most complicated situations. The most complicated people. It’s not about fixing people, it’s about understanding them and adjusting your approach accordingly. Expect the complexity, prepare forward, and lead with intentionality. Now, here’s the deal. Leadership isn’t rocket science. The bad news is, it’s harder. Rocket science deals with predictable physics.
Ryan Leak:
Leadership deals with unpredictable humans. Each direction of communication, whether down to your team, across to your peers, or up to your boss, requires empathy and adaptability. Here’s the big secret. Most people aren’t trying to be difficult. I’ll say it again. Most people aren’t trying to be difficult, but they are trying to be understood. And your job as a leader is to adjust your approach to meet people where they are, not where you wish they’d be. Hey, everybody, Ryan Leake here and I’ve got some exciting news for you.
Ryan Leak:
Data Grow is just a few weeks away and it’s happening on March 19th in Orlando, Florida. And I cannot wait to see you there. I’ll be talking about my new book, how to Work with Complicated People. And let me tell you, this message has the power to change the way you lead and live. And it’s not just me. John C. Maxwell is going to be in the building. Tim Tebow, Stephanie Chong, Jesse Itzler and an amazing lineup of speakers will all be there pouring in to you.
Ryan Leak:
But here’s the thing. Seats are filling up fast. So if you haven’t registered yet, now is the time. Don’t wait. Make the decision today to invest in your personal growth. I’ll see you, my friend, in Orlando, Florida on March 19th. Let’s grow together.
Perry Holley:
Man.
Perry Holley:
I like Ryan. He is smooth. I just love his communication style and the way he presents the message. And so the book is fantastic. You’re going to love that. But what I love, he really starts right off the bat in that segment there about the complexity of leading in all directions, up, down and across. And it really fits in perfectly with John’s message and a lot of our teaching on the 360 degree leader and the 360 degree elements of influence.
Chris Goede:
What’s your thoughts on 100% agree. And this is such a topic that I know you’re extremely passionate about is this 360 degree influence with multi generations. But now we’re even talking about the different types of people in those different categories, right? Leading up, leading down, leading across, leading self is obviously the most important part there. And the biggest thing is I want to go back to something that Perry and I talk a lot about. It’s not about the position, it’s about your influence in those situations. I was just on a call with one of our team members and I was talking about the fact that, hey, I know you want to lead, but do you understand that you can lead without me saying you are the leader and you can lead me by influence. You can lead your peers, you can lead those that maybe are helping you do the work and so understanding that and any level in the organization simply by adding value to People building relationships. Your favorite phrase of making sure people are seen, valued and heard.
Chris Goede:
When you’re doing that in all directions. Okay. You are increasing your influence. And so I love what Ryan’s talking about here because I think it fits perfectly into John’s 360 degree leadership.
Perry Holley:
Yeah. He specifically mentions about leading down. So people that would report to you that you’re the, you supervise these people that uh. I love that you said they, you’re leading down is complicated because they, they expect you to have all the answers. And maybe it’s because I’ve been working for you for so long that I don’t, I don’t really expect.
Chris Goede:
I’ve been waiting after my opening, I was waiting for some type of. Yeah, no, listen. What is it you say the three most famous words are? The hardest words for a leader to say is I don’t know, I don’t know. And I’ve heard you say that. And, and so yeah, that is something as a leader that you just need to be comfortable. Even if you don’t have all the answers, it’s still better to value the people and to walk through that process with them so that their voice is in the mix. I’m a big believer in no matter if they’re complicated or not, whether, whether they’re a peer or whether it’s my leader, Mark Cole, in a certain situation, I want their voice to be heard in the conversation because I want my voice to be heard in a conversation. And when that happens, then I know that they’re investing in me.
Chris Goede:
I know they’re willing to develop me the way that I’m thinking. And, and by doing that, it increases my influence. So you don’t have to have all the answers now. You got to go find the answers. Say, hey, I don’t know, but I’m gonna go find out. And then you gotta deliver on that promise. But you don’t have to have the answers.
Perry Holley:
Yeah, I love it’s the opportunity for you to get, like I said, other people’s voices into the mix is that you don’t have to have all the answers. You, you probably do have a point of view, but that’s your point of view and that sort of thing. He then, you know, you think about leading up, leading down, leading across with leading with your peers, influencing your peers. He said there could be some complic because of competition or how that works. I think this is, to me, when we teach this, I think I am focused almost 90% on leading down. Am I being a great leader for my team. And then I’m so busy trying to lead up and keep my boss happy, I don’t even think about my peers. But I think it’s one of the most overlooked areas of potential growth on the team and in the organization.
Perry Holley:
When the peers are clicking together, when the peers are collaborating, when the peers are looking out for each other. There’s so many things that my peers have learned that I haven’t learned or seen that I haven’t seen or done that I haven’t done. What am I tapping into that? Yeah, no, we’re all running at different speeds. What’s your best practice on getting this peer thing down?
Chris Goede:
Yeah, I want us to talk about just for a few minutes. We have the privilege of. You guys have had the chance to hear from Brian Porta, executive vice president at Hendrick University. Well, along with that partnership comes Hendrick Motorsports. And it’s four race teams, right. And Mr. Hendrick is so big on these statements of, hey, we’re going to collaborate, right? And then we’re going to all compete, right? Right now when if it came down on Sunday and all cars are racing, that you’re on your own and the final lap and you’re, you know, all tied. It’s.
Chris Goede:
But may the best man win. But how do we then across with our peers create this team player, team culture, feel and, and gain respect from those that are our peers that are doing similar work, leading at the same level? In this example of, you know, Mr. Hendrick and the motorsports teams, it’s probably not perfect. It’s not perfect. They’re not sharing everything. But man, they come together as four racings. And I remember watching at the end of last year as they were making their way to the finals and when one knew that they were out, they were sending maybe a tire guy that needed another pit crew or they were giving them information or they’re working together. And I look at that and John did a lesson for them several years ago and it was, hey, how do we, how do we complete not compete against each other in this world? And what does that look like? And, and that’s what, that’s what right here, that’s what they’re talking about, is that when you’re leading across, no matter what type of person they are, how are we collaborating versus creating this competition? And by doing that, I think you have a chance of increasing your influence at a higher level than ever before versus, like I almost see and you probably back even in IBM days, I bet you probably had a lot of peers that are like I am not going to tell Perry Holly what was working in my department because I don’t want him to get a promotion over me.
Chris Goede:
Versus Rising Tide raises all boats. It’s like they get into these silos. Yeah.
Perry Holley:
It’s a great example in the Hendrick Motorsports because we were. Last time we were there, Jeff Gordon was actually telling us, telling us about how they basically changed their locale. They. They moved the teams into the same. They were in separate buildings, separate everything. Separate everything. And now he said, no, we work together, but I want to beat you on. On Sunday.
Chris Goede:
Sunday.
Perry Holley:
But I. I’m going to help you along the way. So, yeah, that’s a great example. Ryan also. So we talked about leading down, leading across, just leading up. Influencing your supervisor, influencing your boss has its own set of challenges. I love. Ryan really called out the intentionality of.
Perry Holley:
You’ve got to really be intentional on all these. But especially leading up, we should just expect this complexity. What are the complications about leading up?
Chris Goede:
Yeah, yeah. Well, I love what he said where he said, complexity doesn’t need to mean chaos. Right. And I thought about that and I thought, oh, I love that. How do I prepare for. For leading up with a complex situation or a complex individual? And I go back to what we talk about at level two, influence, where we go, man, you got to do your work. You got to know how are they wired, how do they want to be communicated to? What are they looking for? And when you do that and you prepare ahead of your opportunities, it’s not luck, Right. It’s just your opportunity to shine.
Chris Goede:
Right. The moment’s there. And so complexity doesn’t necessarily mean chaos. So what are you doing before the moment, to prepare in the moment so that it doesn’t seem like it’s chaotic. And I think by. If you did that, for example, let’s say I was leading up to you and I understood your personality, I understood how you wanted to receive information. And then all of a sudden you begin to trust me a little bit more. Right.
Chris Goede:
And I do that consistently and we’re delivering results together. That whole thing just raises up my influence. You, no matter how complicated you are, how complex the situation is. Because I did the work prior to being able to lead up.
Perry Holley:
Yeah, fantastic. Ryan talks, his little statement, he slips in there, but it’s, I think, profound. He said, meeting people where they are, not where you wish they were. And this again, being intentional about. People are different. They’re not like you. They’ve got different motivation, different desires in the role. But what’s your Thought about, you know, do we meet people so tempting to wish they were in a certain place and.
Perry Holley:
But they’re not. They’re not there yet.
Chris Goede:
Yeah, no, they’re not. It goes back to, again, a statement that, that we say here at Maxwell leadership is that everyone deserves to be led. Well, well, the only way for that to happen is to lead them the way they need to be led. I know you’ve had many coaching conversations, right, about leading different types of people on these executive teams. And you’re like, well, what’s their personality profile? What’s the family name? What’s. And they don’t have answers for you. Right. They’re like, I don’t know.
Chris Goede:
I just, I told them to do X, Y and Z and they weren’t able to do that. And so I think at the end of the day, people are not trying to be difficult. They’re wired certain ways. They just want to be understood. And it’s our job as a leader to figure out how do we get to a place to where they feel understood, where, how do they feel seen, valued and heard and everybody that’s a little bit different. And, and you got to understand that as a leader.
Perry Holley:
So it just, sometimes it really boils down to how do you see people and do you see them as a tool to be used, or do you see them as a relationship to be created and cultivated? Do you see them as somebody to be loved and cared for? I mean, sometimes I think the better you see people, the more you can tolerate their complications down the road because we all are complicated in some way. But if I see you as a valued member of my team, you can be as complicated as you want. I’m going to work with you to navigate that.
Chris Goede:
Yeah. Well, as we wrap up, I hope you enjoyed that little sneak peek from, from Ryan. And I hope you went, still, listened, came back, listened and pre ordered Ryan’s book. But I love a couple of things that he talked about and I just want to wrap up with this, is that. And Perry just hit on it a minute ago, leadership deals with unpredictable people. Right. It’s not the same process over and over and over again. And that’s what makes it a little bit hard as a leader.
Chris Goede:
If you’re going to influence people, then you’re going to get, you’re gonna have to get to know people. You’re gonna have to understand that there may. They may seem chaotic, right. But it’s not necessarily, they’re not necessarily complicated. They’re just, you got to get into their yard you got to be curious enough to get into their yard. And he also used another example just in that short clip about the IKEA furniture. Oh my gosh, that’s so. Can you imagine putting together an IKEA piece of furniture without directions and then having two or three people yell at you? I can’t even measure things properly.
Chris Goede:
We’re not going to talk about that on this podcast, but do the work. Be intentional about every single person on your team, whether you get along with them or maybe you don’t. I think if you spend some time and you’re intentional about it, you’ll be able to increase your influence, whether it’s your leader, whether it’s someone that works for your team or it’s one of your peers.
Perry Holley:
Absolutely. I look forward to Ryan and telling us more and teaching us more on those topics. You can learn more about these, the book and the offer that you want to get on that, as well as more about our offerings, other podcasts, and our podcast family. You can do all that at MaxwellLeadership.com/Podcast. You can also leave us a comment or a question. We love hearing from you and we’re very grateful you’d spend this time with us. That’s all today from the Maxwell Leadership Executive Podcast.
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