326 - Building a Winning Culture with Kyle O'Malley - John Laurito
Episode 326 Building a Winning Culture with Kyle OMalley Tomorrows Leader Podcast with John Laurito

326 – Building a Winning Culture with Kyle O’Malley

In today’s episode, host John Laurito talks with the President of Walton Insurance Group, Kyle O’Malley, about the importance of servant leadership and building a winning culture in an organization. He also talks about the challenges he has faced since becoming president of Walton Insurance. He also shares his advice for leaders looking to improve their company’s culture.

Kyle O’Malley is the President and Shareholder of the Jackson, Michigan-based Walton Insurance Group. He is also an active Senior Advisor and Board Member of Worth Investment Group, a Michigan-based privately held diversified financial holding company, and serves on the Board of the Judson Center, one of Michigan’s largest not-for-profit human services organizations. Kyle is a Past President and Secretary of the Board. 

He grew up in Kitchener, Ontario, where he played and coached youth hockey, and moved to Michigan in 1997 to work for Penske Corporation.  Kyle has been actively coaching and managing Michigan youth hockey teams within the Ann Arbor Amateur Hockey Association, the Victory Honda Hockey Association, The Farmington Hills Hockey Association, and the Compuware Hockey Association. Kyle lives in Ann Arbor with his wife, Chris, and their four children.

Reach out to Kyle:

[0:00] Intro

[1:50] What does servant leadership look like to Kyle?

[3:21] What are the challenges that Kyle faces right now?

[5:53] How does Kyle deal with someone who’s underperforming?

[7:34] How does he find the balance between being empathetic and allowing excuses for underperformance?

[10:48] What are the communication mistakes that leaders often make?

[13:41] What action steps can leaders take to improve their culture?

[19:59] Outro

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John Over the last two decades, I’ve been on an insatiable quest to learn everything I can about leadership. What makes the best leaders so good? After running companies small and large over the last 20 years, today I speak on stages all across the world to audiences who are interested in that same question. My name is John Laurito. I’m your host, and I invite you to join me on this journey as we explore this very topic and what makes the best leader so good. Welcome to tomorrow’s leader. 

John All right, tomorrow’s leaders. Today’s guest is Kyle O’Malley. He is the president of Walton Insurance Group. I loved my conversation with Kyle. Kyle’s a guy very down to earth. I mean, I can almost get a sense of what the culture is like in his organization. And that’s his like major priority is building the right type of culture. This guy is a servant leader. He explains kind of his philosophy about it and you know, how you kind of balance one of the big questions I ask him, how do you balance the whole, you know, being empathetic, but at the same point, not letting people get away with excuses and letting that kind of justify inaction or lack of performance? This is a, you know, very challenging topic for a lot of leaders. And I think Kyle really hits it right on the head. So you’re going to like this one. This is Kyle O’Malley. All right, Kyle. So, first of all, great to have you. And there’s so much I mean. Yeah, absolutely. There’s so much stuff I want to talk to you about and lots of leadership questions that are on people’s mind. I love talking to successful leaders and especially leaders with your mindset. I know you you really come from a place of servant leadership. And I can almost imagine the culture of the organization that you lead at Walton Insurance Group. Talk talk to me. Talk to the audience about that. What is servant leadership in your mind? What does that look like? 

Kyle Yeah, you know, you know, I was I got my I got the majority of my leadership training, if you will, by following and watching Roger Penske, a gentleman I worked for for many years. I’m sure people know that name that are listening to this podcast. He’s an amazing individual. But, you know, Roger was always, hey, what can I do for you? How can I help you? And in the way Roger led, in the way I lead today is, you know, we’re going to give you all the tools, all the things you need to be successful. All you need to do is just apply yourself in our model and within our culture. And we’re there to help you. We’re there to help you get better. We’re there to train you were there we surround you with qualified people that know what they’re doing and and getting into the insurance business like we do. You don’t even have to know much about insurance as long as you’re a person who is a self-starter and eager and hungry. And those are the types of individuals that we’re looking for, you know, to grow with in our organization, because we’re going to give you everything you need to be to be successful. And that’s a big part of the servant leadership in my mind. 

John Yeah, I think there’s that’s lost on a lot of leaders. Unfortunately, it seems to be so much about driving results and just coming down with a certain agenda and mission and and really this myopic focus. What are the what are the big challenges that you face right now? I mean, your lead, a big team. You’ve got a large organization that’s growing you as a leader right now. What’s the biggest thing that kind of sticks in your mind? That might be the biggest challenge that you face? 

Kyle Yeah, you know, I think the biggest thing right now is just the change in the workforce. You know, the younger you know, I’m 56 years old. We are the founder of or the co-founder of Walton Insurance Group, Rick Wall, and he’s a seven year old individual. And then we have 35 year old people on our leadership team. So, you know, those are obviously three distinct different perspectives in many ways. But in the end, on the other hand, it’s a great balance because we get this kind of old school management, we got this new school management, and then I’m in the middle thinking, Well, yeah, that is kind of we should do it that way, you know, the way of the millennial way. But I also, on the other hand, had that same kind of influence in my life when it comes to leadership or that, you know, you kind of do it the old school way. So I think the the really the big challenge today is, is how do you manage that workforce and with a positive influence on them to motivate them but motivating them, delivering that message in in a different way, you know, the old way of, you know, let’s say getting a let’s say a sales guy he was on his meeting is goals. You know, you need to start meeting your goals and that you know, if you don’t do it right now, you’re going to be whatever that doesn’t work today. That clearly doesn’t work today. And you have to take other measures. The message is don’t change the I shouldn’t say the message is the foundations of hard work. You know, do what’s right for the customer, all those types of things that none of those things change. But how you deliver that message to the to the employee, to, you know, have them absorb those types of qualities and them as an individual and carry them out in the in what they do on a daily basis. To have your customers attached to you and have people that you work around attach to you. That’s it. That that’s the trick today. And and so much of that is it’s really just knowing your people and and understanding, you know, who you how how and who you communicate with when you’re trying to deliver that, you know, that type of strategy. 

John So how do you deal with someone who is underperforming? What is what does that look like? Because that’s a that’s a challenge a leaders face. 

Kyle Yeah. You know, I think it’s just a matter of sitting down with them and say, hey, what’s going on? You know, are you having some struggles in your life? You know, we don’t always know what’s going on outside of work with an individual. So I always like to start there. And if there’s some issues there, then then we deal with those. If there’s no everything’s great, then okay, then what’s going on at work? What’s what’s happening here that is holding you back? And and that’s the way I approach it. So what’s holding you back versus, you know, hey, you’re not you’re not performing. I come at it from the standpoint of what’s holding you back. What can we be doing better so you can be more successful? Mm hmm. And then that’s where. That’s that. That’s where I like to start that conversation. Yeah. And and then we can, you know, we can look at a number of ways of making taking some corrective measure after that, whether it be a a performance plan or a follow up plan or hey, I’m going to check in with you every month. Let’s have a coffee, talk about it, see what you’re doing. You know, those types of things. Again, that servant leadership style of what can we do? What can we do to make you more successful? Not me for saying to them, Yeah, you’re not making us successful. 

John Yeah. 

Kyle I just. I just it’s about them. 

John I love that. And it’s really, it’s seeking to understand. And you’re almost assuming that it’s something external, that you’re not assuming that it’s that they are choosing to not work hard or choosing to perform right at a poor level. You’re assuming that there’s some kind of obstacle and you’re looking for a way to remove that and help somebody help them. What how do you. Because there’s a fine line almost between being empathetic and seeking to understand and allowing excuses to come in and those excuses to really validate their lack of performance. How do you find the balance between that? 

Kyle Yeah, well, that goes back to my consistency message. So, you know, we got certain certain metrics of performance, certain, you know, key performance indicators or whatever and whatever you want to call them. And being consistent with that message. And I think if you stay consistent on that, you know, whatever it is you develop together to help them get better, then then you have to be as a leader aware of if you’re if the individual’s trying to kind of get off that path, you know, you sit down to agree to get on a path to to get better together, not not separately get better together. And if one and if you’re consistent in that message and they’re not being consistent in that message, that’s where you have to. Hey, what’s what why are we why are we going away here? Like what? What’s happening? And if that continues to kind of get off the path, then then maybe it’s just not the right industry for them. Maybe it’s not the right position for them. Maybe they’re in the wrong seat. You know, there’s even another level below of, okay, you’re not performing at this, but maybe you’d be really great at this in our organization because we have so many different ways and and positions in the organization where a person can be successful. So sometimes I’ve found that when you start a process like that, ultimately you come to realize that, you know, they’re not a real sales person or a producer. They’re more a they’re more a hunter. A hunter person or they or there may be more a farmer, you know, type of person where you you give them and you give them stuff to work on. And then they, you know, they, they perform and, and do all the daily stuff really, really well. But they’re not good at, you know, self-management or self directing or self-starting in those types of things. So yeah, again, that goes back to the consistency of the message. If I remain consistent and our management team remains consistent, then those in a conversation like that or a plan like that, if they’re getting off the tracks, then you say, Hey, that’s not what we agreed to. What’s going on? So you just kind of always come back to that base foundation that you established. And then if they’re getting off the path and there’s, there’s, you know, some deeper reasons that will ultimately be uncovered. 

John Yeah, great, great. 

Kyle Sometimes it’s just not for them, you know? Sometimes it’s just not for them. 

John That’s okay. Exactly. And you have to be able to figure that out when that time is and and lead them, you know, lead them in a different direction because, you know, as well as helping the organization. 

Kyle Yeah, I think so. Too many times as leaders, we the like leaders jump to conclusions. Mm hmm. It’s just not going to be good enough at it. Yeah. I take it from is that someone will say that to me. I say send them over to Coach Kyle. Coach Kyle’s going to going to help them. And if I can help them, then, then then I know what you know. We’re where we are. Yeah. So I think so much of it is is just that is coaching. 

John Yeah. Let’s talk a little bit about communication. You know, that’s such also a big topic in the leadership arena. And leaders are always learning and trying to figure out ways to communicate better or whatnot or organizations better. What is what are some of the mistakes that you see when you think about your leaders that don’t communicate well or organizations that don’t communicate well? What does that look like? 

Kyle Yeah. You know, I just think, you know, you leave you leave people too many to to establish or under, you know, answer their own questions. You know, I don’t want people, you know, assuming certain things. I think it’s important as a leader that you set the path of of where you’re going and have an open door policy. And if people feel like somewhere in the organization, we’re not going on that path that’s been set, then as leaders, we need to know about that because we make mistakes, too. And if I need to be course corrected by a handful of people in the in the organization that say because, you know, we were you know, we we met as a group, the center is where it going. Doesn’t really feel like that, you know, what’s going on. And and so, you know, we seek that feedback. We want that feedback. And then if there is a change that needs to be made in that regard, then we make change. And it’s just to me, it’s just that simple. And but if you have closed door policies and, and you’re not interested in that employee feedback, then it’s really not going to be a successful culture within an organization. I think, you know, John, that many people have said this before. Culture is king. And, you know, I came to Walton in 2018, you know, as a seven year old business family, family run. And obviously there’s a culture there. But obviously, after seven years, there need to be some changes. And it’s not that there was anything wrong. It said, if you want to get to the next level, we’re going to have to have some different way of how we do things. And and so you have to kind of very slowly make those it’s more tweaks than it is sweeping changes. And if you do that correctly over a three or five year period, you’ll be pretty successful. And that’s what we that’s what we’ve done in the last five years under my leadership here. So it’s been it’s been so much fun. 

John That’s great. Well, I can again, I can imagine the culture of your organization just in the brief time. We’ve got a chance to know each other. And it’s amazing. You know, I, I travel around all over the place and I go to different organizations and work with different teams. And I see you can walk in instantly or get on a call with a group of people and instantly see and feel a culture. You’ve got a lot of leaders that might be listening there that are very understanding of the importance of culture. And culture is king. I agree 100%, and they want to start making an uptick in it. They want to change it, they want to turn it around or they want to improve it, even if it’s good. What? What’s one action step for leader? What’s one thing that you might tell them, hey, you know, if they can leave this podcast and do this one thing, that might make even a little bit 1% difference tomorrow, what might that be? 

Kyle Yeah, I think I really do think you have to meet as a group at least once a month and and not and talk about results and but talk about other things. Celebrate successes in the organization. Celebrate testimonials of of the receptionist that, you know, gets a testimonial from an outside customer that says, Hey, every time I call the wall in the chair scoop, I feel like family. And it’s because the first person that answers the phone treats me like family. So I think you got to really, really connect with each other, talk about the good, talk about the bad, talk about things you can do better, talk about your results. And and again, this, this this for me comes from my years with Penske’s organization. And he did this with thousands and thousands of employees and, you know, shares the financial performance and, you know, and how and how good of is and what where he felt we could improve. And and it was it was always in a team effort on how we could improve. So I think when you start that monthly communication process as a group and and sometimes to groups so big, you have to figure out how to do it and you know, and bite sized chunks. So maybe you may have to if you’re a leader in a organization that has shift work, you’re going to have to come in in the middle of the night and and have some of that communication. You know, and this is these are things, again, that Roger used to do at the UAW, at Detroit Diesel. You know, they for they communicate with thousands of people over the course of a week, every every quarter. So, you know, sort of more for for them because of the size of the employees but the size of the employee group. But that monthly meeting for us, we gather again talk about what’s going on in each area of the business and celebrate successes, wins, losses and what we can do better. And and I think if you do that, I don’t think I know if you do that generally, if you’re happy at work, you’re happier at home. So ultimately, what we want people to be able to leave here at the end of the day and get home and have a great home life and not be worried about things that are going on at work and then at that perpetuates into a better home life. So when they come into work, they’re in a better frame of mind to be here. So we want as much as we want to them, to them enjoy a family at home. We want them to have a family here at work as well. And sometimes that’s a that’s sometimes the only stability that an employee may have because maybe they have a poor home life. So we feel if we can have an awesome work life and work family, that there’s trickle down effect with that or or conversely, it’s it’s where they come to feel wanted and needed and and appreciated. And I think that has a lot to do with, you know, success today. And I’ve always been a believer as all things start at home, but they can also start at work. And that’s what I’ve learned more in my you know, I have four kids. We have four kids, and I’ve been fortunate to have great home lives. And, you know, my parents family, they’ve all been a big part of my you know, my personality, character, etc.. But I’ve come to realize more and more that works an incredibly important place. It’s where you spend like at least half of your time. Yeah. And, and fortunately, throughout my life, I’ve been exposed to great jobs and great leaders and and I didn’t always feel this way, but I do now that I have these 60 people that I’m responsible for and and I want that responsibility. And I was seeking that responsibility and I wanted it. And so now I’m embracing it and, you know, trying to do my best to help people be better. 

John Well, you, too. It sounds like you’re certainly doing a phenomenal job. I love your insights that you’ve shared. I know, unfortunately, we’re short on time here, but I know there are listeners that are going to want to get in touch. We’ll put all your info in the show notes there. But Kyle, congrats, first of all on your success. I understand obviously the organization is grown and doing tremendously well under your leadership and you’ve built this team. So keep up the great work. 

Kyle But it’s a team, you know, it’s just it’s just one person. You know, I always say, you know, management is one plus one equals two leadership. That’s like one plus one equals four, maybe five, maybe one plus one equals zero. Yeah. You know, it’s addition by subtraction, you know. So I think as, as, as leaders, you got to, you got to surround yourself with other great leaders. And and we have that here. There’s you know, we couldn’t do this with I couldn’t do it without, you know, the people that we have and certainly without the employees that we have. So it’s just it’s just really, really fun. And and I think if you make it fun, you know, it’s it can be a great place to be and people enjoy that. 

John Excellent. Well, thank you for joining us today, Kyle. I appreciate it. I hope you come back another time. We will take a deeper dove on one of these topics. 

Kyle Yeah, I would be happy to do it. John, anytime you want to chat. 

John Excellent. And thanks for joining today on today’s episode of Tomorrow’s Leader. We’ve been here with Kyle O’Malley, the president of Walton Insurance Group, great organization. We’ll have all the information about Kyle and Walton Insurance Group in the show, notes with links and all that kind of good stuff. In the meantime, like share, subscribe, go down below, give a five star review and we’ll see you next time. Thanks. Thanks for joining. 

John Us on today’s episode of Tomorrow’s Leader. For suggestions or inquiries about having me at your next event or personal coaching, reach me at John@johnlaurito.com. Thanks, lead on!

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