
Listen to this leadership podcast with Tom Wilson, Chair, President and CEO, and discover the power of managing your time and dialing in your purpose.
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Podcast Host
Hello, everyone, and welcome to another episode of How Leaders Lead with David Novak. Today, we've got Tom Wilson on the show. Tom's the chairman and CEO of Allstate Insurance, which is arguably one of the most recognizable insurance brands in the world. Now, in his role as chairman and CEO, of course, Tom knows that time is the one resource that leaders cannot get more of. And you'll hear many times in the episode why he believes every leader ought to be brutal with their time. Now, this discipline with time, though, isn't about shutting people out. It's about being present for what really matters and staying deeply connected to your people and to your purpose. You're going to love this conversation between David and Tom. And be sure to stay tuned to the very end of the episode so you don't miss the debrief. Enjoy.
David Novak
I gotta ask you, you know, was there ever a time in your life that you wished you had insurance, but you didn't have it?
Tom Wilson
Yes. I was on a trip with some friends in Wyoming. We were using ATVs. The guy wanted to charge some huge amount of money for us for the two hours. I said to my friends, don't do it. It's a ripoff. I crashed my ATV and it cost me $500.
David Novak
Well, that'll teach you. Yeah, like. Like, I'm like, see, you know, Allstate, everybody knows Allstate's in big time into college football, and all the teams have mascots. There was a mascot that represented you as a leader, Tom. What would it be and why?
Tom Wilson
Wow, that's a really good. Because it's. I suppose it's gotta be both funny and memorable. Does it have to be a thing, or could it be. You name it, I guess it should be a thing. It would be something that was both welcoming and you felt comfortable with, but it would also had a part. So somebody once described me as somebody that wore velvet gloves but had steel hands underneath. So maybe that would be it. I don't know. I feel like I'm respectful and I embrace people, but then, like, when you've gotta be hard, you just have to do that for them and for the company.
David Novak
It sounds like you might be a teddy bear that could turn into a grizzly bear.
Tom Wilson
I like that. That's one of those morphing things.
David Novak
Yeah. Well, I can't wait to dive into how you're leading Allstay.
Tom Wilson
But.
David Novak
But first, I want to take you back, Tom. You know, what's the story from your childhood that shaped the kind of leader you are today?
Tom Wilson
Well, I Mean, you always. We think we fall farther from the tree than we do, but we are all, you know, products of our parents. I had two really terrific parents, very engaged, loving. And they had a couple of things that they just drilled into us. One was just be the best at whatever you're going to do. Like, they would. Literally, they'd say, you can be a trash collector if you want. Just be a really good one. Secondly, it was always about respect for other people. So it was, you know, you're no better, no worse than anybody else. Whether you have more money, less money, you're all the same. And I think the third, I think David would be community involvement. Like, we always had something going on. There were people giving out meals to elderly people. We had signs on our lawn. I mean, it was just. My parents were active in the community, so those would be the three things I think that kind of drove me.
David Novak
What did that community involvement teach you about leadership?
Tom Wilson
First, you have to start with respecting that somebody can be an individual. Second, you have to accept that it's okay for them, even if they don't agree with you. That's okay. It's their point of view. And so my parents were very good about navigating down the middle as opposed to falling into. You don't believe what I believe, so therefore you don't count.
David Novak
Now, as you got into business and you were coming up, was there was who influenced you the most as a leader? Either somebody you work for or maybe somebody you might have read about.
Tom Wilson
Well, first, I would say, David, like you, I'm sure I've had lots of people who helped me. Some directly, some just watching them. You know, I'm a big believer in, like, you know, learn leadership lessons by watching other people. So this podcast is actually quite good for that because people can learn from that. If I had to pick an individual, it'd probably be Ed Brennan, who was the CEO of Sears. I worked for Sears for about two years to help him bust it up. And Ed was just great at people like I. So I asked him, I said, hey, will you? I don't know anything about retail. I'm working for Sears as this giant retailer. But you also own Coldwell Banker and Dean Witter and Discover Card. But you know what? Take me to some retail stores and show me what you know. And so we're in a store in Brooklyn, and this old, little, old man walks up to us and says to Ed, you don't remember me? And keep in mind, Sears got like 600,000 employees at this time. And Ed says, give me a clue. And the guy says, well, actually I never worked for you, but my brother worked for you. And he said your brother's name was X. It was when I was in Atlanta 30 years ago. And your name is X. And he got the guy's name wrong, but his brother's name right. And the guy and I, and I walk, we walk away. And I said, ed, that is like amazing. Like, how did you do that? And he said, you know, people are the key to all success and you focus on what makes you successful. And so since then, I've always thought. And it kind of reinforces what I was talking about. My parents, like, people count. People are the be all and end all of success. And so Ed was, you know, really helpful in having me think that through.
David Novak
Yeah. So you went to Sears to basically bust it up, and you had to learn a lot just by looking at the demise of what had to be one of the great American companies at one point in time. What did you learn from just what can go wrong by looking at that situation?
Tom Wilson
Sears is both a terrific story of risk taking and seeing market and customers and then losing its way. So, you know, Sears was basically Home Depot, Walmart, everything, all rolled into one. And they did things. And when I worked for them, they had expanded successfully in real estate to call a banker. They started Discover Card from Spit. You know, it was nothing. They were doing Prodigy and online service. And so they had this long track record of very being successful by focusing on customers. What happened, I think, was they quit looking outside. So I'm a big believer in bringing the outside in. I'm always out looking to say, what do we have? What are we doing right? What are we doing wrong? So you got to bring the outside in, and then you have to have the courage to change. What happened was they were successful. They weren't doing as well as they want to. They didn't look outside, they didn't say, hey, we need to change. And they made small change, not big changes. And so as a result that, you know, Sears no longer exists.
David Novak
Yeah, absolutely. It's a tragic story, you know, but your, your career has been illustrious. You've done many, many big things in your career. But what, when you were coming up, what, what kind of, of work did you raise your hand for early on, you know, and, and, and how did that shape the path that you ended up on?
Tom Wilson
Well, sometimes you raise your hand, sometimes you get drafted, you know. So I would say what I first got drafted for is I was and probably, I guess Still, I'm a pretty good problem solver. Like, I can look at a situation, I can think about it from all different angles, and I can say, okay, here's probably the path out of here. And it's. And, you know, and if that doesn't work, we can try this. So I think that's what kind of got me started. It got me a leg up. I think what's happened after that is I've started to be more focused on what really matters. Because there's a lot of stuff you can do that just work and you got to do it. It's kind of like being at the river and, you know, paying it for gold. Not every time you stick the pan and there's gold come up, but deciding that you're really only going to focus on the stuff that matters. And so that's really what I've morphed into, is finding those big problems that will matter if I fix them and lean them. So when people ask me to do, like, you know, you can ask me, I'm like, I'm sure you're on a bunch of, like, social organizations, stuff like that. I'm like, if you can tell me what needs to be fixed and it's a big thing and I can really help you, I'm interested. Other than that, I'm not interested. So it's really about being brutal with your time.
David Novak
Being a problem solver is a superpower of yours. This is something that's, you know, you've been able to differentiate yourself as a leader. You know, how do you go about solving a problem? What's your. Do you have a process for it?
Tom Wilson
Yeah, I suppose there's a process. First is being prepared, really looking at all the facts, trying not to have an opinion right away, which is hard. But, you know, I'll be accused of a lot of things in my life, but it won't be not being prepared. I'll know this stuff down deep. The what I've now morphed into is trying to not use. Come up with my own solution, but to help other people craft solutions. So I've become less of a problem solver, I would say, David, and more of a facilitator with a little nudge every once in a while. Because what I found is when I just came up with a problem and other people didn't buy it as theirs or their solution, then I was pushing a rope uphill. So what I've morphed into is trying to find ways to help other people see what I believe to be True. And then help find a way to. I've become more like a maybe I moved from problem solver to transportation engineer. You know, I'm kind of like, I kind of like, I say, okay, here's the way the road could go. I help build the road, I make sure there's no ice on it. Then I stand by now, the one thing I have learned, one of my directors said this about me. Tom has to know. You know, if Tom knows, you know you're going to be good. If Tom knows, you don't know and you don't know, you don't know. Tom's going to be really helpful. He'll help because he'll know the details. Like, you know, he'll, he'll help sort it out. If Tom knows, you don't know and you don't know, you don't know, you're going to have a problem. So I spend a bunch of time and that's where I've had to change as a leader. I would use my knowledge and problem solving ability to question people to see if they knew. And once they knew, I was hands off, like, here's come to me for help, I'll do this. People saw that though initially as I wanted to do their job and I wasn't trying to do the job. So I've had to get better at saying, look, I'm going to ask you a bunch of questions. But it's not because I really think I know the answer. I just want to know you know the answers to them. Because if you know, then I'm going to go with you.
David Novak
So you're this, you're this transportation engineer. You help people solve the problem and you, you know, give it, you ask them the right questions and kind of lead them down the, down the road. What would be a problem that you and your team have solved that was, was the most complex that you're most proud of?
Tom Wilson
Well, they're probably. I'm going to come back to the most proud of because that's a different answer because it's not really that complex. But I think it gets to the essence of kind of how I like to lead. Complex problem. We decided, we had been about seven years ago, we decided that our high good value, decent price strategy wasn't picking up market share. So we had to do something differently. We decided, you know, it's all about the cost, stupid. So we got a lower price and we set off to do that and we created this thing called transformative growth, which at some point, if you're into I'll talk about middleware. But it was, how do you get from your vision to day to day activity? And it required us to change our distribution, our cost structure, our new products, our technology was everything. And so we went out to all these consultants and we said, what do you think? They said, we think you're taking on too much. And I'm like, what would you not do? Like, which one would you cut out? They're like, well, you kind of can't cut this one out. So we took on transformative growth. We're about 60% of the way there after six years, a lot of angst and turmoil in the company, but it's working like there are certain places that were really picking on market share and we feel good about it. So they. That was the most comprehensive thing I've ever taken on and our company's ever taken on, to be honest. And we're not done yet. So I can't like wave the victory flag yet. But had we not done it, boy, we would have struggled much more in the pandemic and we would not be in a good place now as it relates to artificial intelligence. So we didn't do it because we knew those were coming. My point would be do the hard things, do the big things. Whenever anything happens, you'll be ready.
David Novak
And you talk about vision and driving it down or up the organization. You know, how do you do that? I mean, that's where you really turn vision into action.
Tom Wilson
I call that strategic middleware. I wish I had known it earlier. It took me about. It could be a decade, David, to figure it out. Twenty years ago, we started with our Shared purpose, which is a document like everybody else has. It's one page thing, helps us align it. And then over the course of time I've tried to figure out how to build middleware to get that purpose, which as you point out, very broad, very encompassing. Ours is they help protect people from life's uncertainty. So it doesn't say auto insurance, it doesn't say home insurance, which is why we now sell 160 million warranties. You know, so there's a bunch of things that were really helpful, but what I didn't really think about was how do you use build middleware. And by middleware I mean think of your brain as the vision and your keyboard as it takes that vision. And then your processor is a bunch of zeros and ones, right? Like that's what your computer does. So think of zeros and ones as the day to day activity. How do you build a series of middleware that takes that vision and takes it down to data activity. So we have a series of middleware. One of our things is we have a two part strategy. It's got two parts to it. Then we have under the increased property liability market share. We have transformer growth that's got five components, five phases. We have an employee value proposition which has got five components to it. We have ally all states, large language, intelligent ecosystems, eight components. So we're constantly trying to break it down lower and lower and lower so that it gets to the day to day activity. And we have things called design, build and deploy plans which take the concepts into what day to day activities. Now you have to be a little careful because sometimes those can be too directive and there's no room for people to maneuver. But if you can build your culture such that you can do that. Building the strategic middleware has helped us take this broad vision, which could be anything, down to I'm a claim adjuster. What am I supposed to do today and why do you want me to use this technology?
David Novak
You mentioned culture. How would a frontline employee describe Allstate's leadership culture in one sentence? What would they say?
Tom Wilson
Allstate believes in being a good corporate citizen and that includes having transparent leaders who respect us and always tell us the truth. That would be my guess. We could ask them.
David Novak
Knowing you, you probably will. You know, you mentioned spending time where it matters most. As the CEO, how do you spend your time to send a signal that this really matters most in our business?
Tom Wilson
I'm going to start at the very top and then I'll come down to how do I allocate my time? First, I think you have to be brutal with your time. And I use that word on purpose, which means there's not. You can't buy another hour a day. Like if I could buy a 25th hour of the day. If you could, I'd buy one. I can't, so I have to use it as if it really, really matters. So therefore I'm very specific about where I spend my time and I don't make my time a free good. Sometimes leaders get caught in the trap of their time as a free good. That doesn't mean that you're not available to people. It actually means you are available to people, but only available on those things that really matter. The way I show that off to our team or lead by example, if that's the right way to say it, is. I allocate my time. I track how many times I'm in front of employees, how many times I speak to them, how many times I'm out with agents. I try to be out in the business and when they see you and you're out there, you can help them see what you want the company to be. And then I also know my stuff, so I'm prepared. When I come into stuff, I know what I'm talking about. I don't like, try to use meetings for education for me because I feel that's too self centered. I might use meetings for education for us, but then what you're doing is highlighting that what a good leader is, is curious and like tries to interrogate the truth. And so it's. But I do spend a fair amount of time out talking to employees and getting them inspired. So for example, a friend of mine who's a ophthalmologist said, hey, you know, he's big, not philanthropist. He said, when I go in these philanthropy meetings with his staff, I play music before. And so I now select the song. Josh GUITAR I select this song. If we're going to have 15,000 employees on a zoom call, I select the song so that it's related to what we're going to talk about. That's inspiring. It's not like elevated music because I feel like there's ways that you can show that you're part of it and there's an emotional connection. So I try to have people have an emotional connection to us and to me.
David Novak
Great. You know, and when you think back on all the things that you've done in your career, was there a leadership mistake that you made early on that forced you to grow faster than you wanted to? Because sometimes when you make those mistakes, it accelerates your growth.
Tom Wilson
Yeah, well, yeah, I've made plenty of mistakes and plenty of what I would say are just economic mistakes. And then I've also made some leadership mistakes. My thought on mistakes is, you know, you just gotta, you gotta be honest with yourself, say, why did it happen? What did you learn from it? And not let it restrict you from doing the same thing again because maybe it's the right thing. And it just didn't turn out right. I've made plenty of mistakes. I would say financially, now there's like a bunch of them financially. I mean, hundreds of millions of dollars. So you just gotta win more than you lose on that. I would say from a leadership standpoint, I don't think it was a mistake, but it was personal growth. So I was frustrated with our team. They weren't getting something done. It was on earthquake insurance and so I said in the meeting, look, I asked for this for like nine months. And I'm going to tell you, if we're back here in three months and it's still here, I'm going to be talking to different people. I overused my position power. I didn't need to do that. I could have done it in a bunch of different ways. And so I try not to overuse my position power. I try to be aware of my position power as a force for good. And when I want it to be a force for accountability, I do it in different ways.
David Novak
Where do you get the truth teller that makes you realize that? Is it self reflection that forces you into a situation where you say, hey, you know what? I didn't need to use my power that way. You know, where do you, how do you, how do you get that kind of feedback or come to that kind of conclusion?
Tom Wilson
I would say, I mean, there's lots of two things I do. Enroll others in your quest to be a better person and listen for the silence. So what I mean by that is I have people I'll go to and I'll say, hey, how'd you think that went? And, you know, you don't need the people who are just trying to be nice to you because they think you're going to help them somehow. You need people to say, you know, Tom, you didn't really do that, right? And so that needs to be a safe place for them and otherwise it won't help you. And the other part is I listen for the silence. Like in my, when I go talk to people, there's always people who come up, say, that was great, you know, terrific. And then, and so you kind of, kind of tune those out. There are people who, if they don't give you balanced feedback and you hear nothing, you should assume you didn't do a good job as opposed to, you know, a couple people told me great, slapped me on the back and I went away and said it was great. I'm like, no, you know, like people didn't really say anything. So listening for the silence, I think is a valuable tool for leadership.
David Novak
Yeah, listening for the silence, that's something everybody should remember. And, you know, when you think about the failures or the mistakes or whatever you, however you want to describe that, you know, and it's public, you know, how do you come back from that? You know, when you make, when you, when you make that mistake, you know, how do you bounce back? What do you do personally to get yourself geared back to, you know, get Back up on you. I like how you said, I've won more than I've lost. You know, I've lost a few million, but I've made more million. You know, how do you. How do you bounce back?
Tom Wilson
Two ways. One is retouch with my purpose, and second is be forgiving of myself. Like, look, I'm not perfect. I've made plenty of mistakes, and I'm not gonna shoot myself in the head every time I do something wrong. But I think the other part is knowing what your purpose is in life. And so my purpose at this point is to help other people achieve more meaning and success in their lives. So when you reached out, I'm like, david's doing what I would love to be doing if I can help. Because that. And so when I make a mistake, I come back and say, okay, did I help other people achieve more meaning and success in lives by trying? This might be yes, might be no, but at least I'm trying to do what I set off to do in my life.
Podcast Host
Hello, friends. I hope you are loving this conversation between David and Tom. As always. Please stay tuned to the very end of the episode. David and I are going to debrief the conversation that he's having to give you some real tangible tools that you. That you can apply right away to your leadership and to your life. Stay tuned to the very end of the episode, and I will see you at the deep read.
David Novak
As I understand it, Tom, you've invested heavily in helping people in your company discover what their personal purpose is. You know, tell us about what you're doing.
Tom Wilson
When I became CEO, I had been president, so we're working on what I wanted to work on, right? And I said, you know, we need a little more energy around here and a little more fast fleet of foot. And so we went to a place called the Human Performance Institute, which I had been through like a one day session. It's a two and a half day session. It helps you figure out your personal purpose. So we went down there. Eleven of us went. One was excited. That was me. And everybody else came back excited because it was about their personal purpose. And so we, and then we said, this is so good for us. We should take it to our officers. So we had 200 officers at the time because it'll help them, because it's all about them. How do you get better? What do you want to get done with your life? Being honest with yourself, building a plan to get better? And we said, well, if we did that for the company or for our Leaders, we should do it for the company. And that's how we came up with our shared purpose. Once we got that, we started taking other employees through it. And we realized if you want to be a purpose driven company, you have to be powered by purpose driven people. So we've now helped 75,000 people figure out what their purpose is and help how to pursue their purpose. And people leave here because of it. Like they say, you know, I always wanted to be a teacher. So, you know, David, thank you, but I'm out of here. And I'm like, God bless you, you know, like, if that's really what you want to do. So when you asked earlier about what I would say, that's the thing I'm most proud of is helping 75,000 people figure out what they want to do with their life. We can make money, we can help our customers, we can do all that stuff. But that's really powerful.
David Novak
Do you have a really interesting story of where you saw someone truly unlock their potential because they found their purpose?
Tom Wilson
Yeah, many. There's one person who was probably the best reinsurance person in the world and went to be a teacher and loves it. He's a math teacher. I have a woman who two months ago came up to me and said, I'm alive because I did the energy for life stuff. And she had a whole bunch of other issues she dealt with through our programs. You know, I think it's good for the company. But the company is not just about making money. We believe that businesses have four roles. One, you got to serve your customers. Two, you got to make money for your shareholders. Three, create opportunity for your employees. And fourth, improve your communities. And that third piece, that's part of what we're about. And I feel great about it. I mean, that's something I'm very proud of.
David Novak
I think you should be. But I think it takes a lot of courage to make a move like that, because I know a lot of leaders who would be, hey, they take the perspective. If I teach somebody how to find out their purpose and it's not Allstate, I'm going to lose a good person if they decide to do something else. I'm sure you had people internally that would challenge you on this when you were getting started or not. And I just.
Tom Wilson
No, I think we, I think we did and we probably do. So let's, you know, like, be honest about that. And we have 54,000 people. And there are sure some people who still think that that's. Don't want to encourage people to do everything. But if you look at your career and, you know, you're a corporate executive, then you're an entrepreneur and starting a business, like, if you didn't have that freedom and if you didn't have somebody supporting you emotionally to get that done, like, how much different would your life be? And so I'm like, if I can help people do that, Allstate will be fine. Like, we'll find someone else to adjust claims. Like, it'll. And it'll work for them, and it might not work for somebody else.
David Novak
Yeah, I couldn't agree with you more. I think purpose gives you joy in life. For me, you know, my purpose is to make the world a better place by developing better leaders. And I'm trying to do that at every stage in life from, you know, early childhood education, you know, all the way up to people who are in business. So. But that. That has provided a real focus. You know, when you think about the purpose that you've identified for. For Allstate, you know, how do you keep bringing that forward and keep reinforcing that in everything you do? Because it's obviously something that you're very passionate about.
Tom Wilson
I am relentlessly boring, and I say it all the time. You know, there are times, David, when I'm like, oh, my God. And I. And I got. I sort of went through phases. You know, first it was, you do it and you create it. You're very excited about it. Then you start talking about. But then you kind of get bored saying the same thing all the time, like, okay, let me talk about our four items. Then you realize that the benefits it can create for other people. You're not really being boring. The words are the same, but you're delivering them to a different set of people. And so everything I do, my team knows, everything I write, I'm always tying it into our shared purpose. When I do an employee communication, we talk about our shared purpose. I'm just always reminding people that this is why we exist. They may or may not agree with us, but at least they know what we're trying to do.
David Novak
So you know what you're trying to do. How is your purpose helped? Maybe change the way how you lead in some. Some. Some way.
Tom Wilson
I think it's helped me let go a little bit, to be honest. So if you. If my goal is help other people achieve more meaning and success in their lives, and then when it comes to a business problem, let's say I think the answer is A and somebody else thinks it's B, I let them Do b. As long as it's not gonna be below the waterline. Below the waterline for us is if it's below the waterline, you take it. You're in a ship and the torpedo goes below the waterline, you sink. If it's above the waterline, you're okay. You don't like having a hole in your ship, but, like, don't worry about it. So on those that are above the waterline, I think it's helped me say let go time. Like, you don't. It doesn't have to be perfect. And you know what? More times than often they're right anyway. So it's not even like I'm giving anything up, but I find that I'm. Hopefully I'm viewed as a more supportive
David Novak
leader, you know, in terms of, like, empowering others. I'm curious. You know, your. Your background is financial. You've been a cfo. You know, you obviously are very well prepared. You know the ins, the details of the business. And yet also not yet. And Allstate has very powerful marketing. You know, you've got the Mayhem campaign. You're in good hands with Allstate. And, you know, so how involved do you get in that part of the. Part of the business?
Tom Wilson
I think so a lot.
David Novak
I figured you would because you look like a guy who's creative as well and you like to have fun.
Tom Wilson
Yeah, I think actually I'm a salesperson. You know, I'm always selling some idea. I actually, when I went to business school, I was. I had a marketing and strategy major. I didn't even have. It was a finance major. But you took like three classes and they gave you a stamp, you know, and so. And then I was. When I was investment banker, I was selling businesses. So it was, you know, numbers are not that hard for me. I'm reasonably easy for me. So I always find that sales skills and inspiring and communicating people are the key parts. And so I find myself always trying to like, it's. I'm selling something all the time. But I was talking to a guy the other day about how do we give credentials for high school and college students so they can actually be employable on something. And he said, you know, the best skill they need is sales skills. Everybody needs some sort of sales skill. So I find like, that I'm mostly just a salesperson. Whether I'm selling you purpose and want you to purpose because I believe it'll be good for you, or I'm selling insurance because I think you need to be protected, or I'M selling shareholders because I'm like, you know, you should invest in us because we're gonna make you a bunch of money. I feel like this idea of being customer focused is really important to success.
David Novak
And, you know, your commercials, your mayhem commercials are really great. Do you have a fun story behind any one of them?
Tom Wilson
Yeah. So mayhem is quite clever. He and I were doing a public service announcement at one point, and he's kind of a wacky guy, you know, and he likes. And we were. It was a football commercial, and he was breaking the table and all kinds of mayhem. And at one point, during one of the breaks, he takes a piece of popcorn, and he looks at me, he says, hey, Tom. And I look at him and he throws it, and he hits me right in the middle of the forehead. And it's on tape. And our team was like, oh, we can't show that. I'm like, you're kidding. That's hysterical. We have to show that. So I'm like, you know, whatever works, Whatever gets people engaged. And if we can have humor, help them think that they should be buying insurance from us, then we're all for it, you know?
David Novak
And anyone who watches college football sees your all state hands catching the made field hole field goals and the extra points. If you had to borrow one leadership principle from the elite college football programs that are out there right now and bring it straight to your all state executive team room, what would it be?
Tom Wilson
It would be on leadership. It would be on collective success versus individual success. So I find sports have this great ability to get people to really put the enterprise called the team first, even though they're all sports stars and they all want big contracts and stuff like that. So I would be like, I like people who bleed blue.
David Novak
Yeah, I know. That's. Now we've got the new mascot, and we know what your color is. Now, you mentioned the importance of customers. How do you personally stay on top of customers?
Tom Wilson
I think it's about being in the business versus over the business. I think too many leaders go over the business, think they're not. And I'm like, you're in talking to employees. You go out like, well, we have a catastrophe. I go out and walk sites, I talk to customers. I'm like, what happened to you? How did this work? And so you're looking at all the small things that happen so that you can add them up and figure out if you're in the right direction. So I think whether that's riding along in a claim, trying to, like, just put your Head in how it's about empathy. So, for example, we just launched something called deductible payment plans, where if you have, you know, you buy insurance, you have a $500 deductible, and you get in an accident, you don't have 500 bucks. Typically you'd say, well, that's your problem. You agreed to 500. We've now started some. In a couple states, we're like, hey, we'll loan you the 500 bucks. And so you're putting yourself in their mindset. And I think you have to be in the business and out seeing people and being externally focused to do that.
David Novak
What's a story that you go back to? Because I imagine since you like to inspire people, you're pretty good at telling stories. And what's a story you go back to time and time again that really captures what being in good hands looks like from a. From a customer perspective. When your team does it right, I
Tom Wilson
would say that the portfolio of stories for us. Cause it's not always the same story is always around a catastrophe. So when a hurricane comes and people, their house gets blown away, all their stuff's gone, they have no place to stay. We're there for them. We have people who, our motor homes are storm chasers. They're getting out there, they're knocking on people's doors. They get them apartments, they get them clothes. We. We have therapy dogs that we bring there in case they're feeling like they lost a pet or something like that. So those stories are very powerful. The reason we use them is because it's easy to visualize them. I think good stories, you have to, as a storyteller, people have to be able to see it visually in their head. But the same thing happens every day. If you're in a car accident, it might not feel like a hurricane hit your house, but it's pretty traumatic. So you. Those stories about catastrophes help us be empathetic for our customers when they need us most.
David Novak
When a major disaster hits or even a car wreck for a customer, what leadership muscle matters most? When you're dealing with a customer, you
Tom Wilson
have to empower those claim adjusters to do whatever it is they need to do to act. And the same with the team. So one time there was a big catastrophe and there was. The cell towers were down and our team was on with a bunch of other industry people. And somebody said, one of the cell companies said, hey, we got 12 extra trucks that satellite trucks. And our person said, I'll take all 12. Don't know how I'm going to use them. And if any of you, if we don't need them all, call me, I'll take them. So it's about acting right away. You know, I need to get you in a, you need to be in a, in a hospital, getting an ambulance, off we go. Like, we're not going to debate what the policy say, what the policy not say. If there's water in your basement, get the water out of the damn basement. And then we'll figure out whether it's covered or not. So I think, and that's true in many things in business, when you're dealing with customers, having people who are empowered and importantly feel empowered, so they're not blaming on company. Well, I would do this for you, but you know, the rules are this, no customer wants.
David Novak
Is this something you think is deeply seated in Allstate or is this something you need to evolve?
Tom Wilson
I think it's deeply seated in Allstating catastrophes. I think it's something we need to involve on normal customer service.
David Novak
And how do you go about driving that home? I mean, how do you make that such a key point?
Tom Wilson
I think there's two ways. One is, I think we have four leadership behaviors that I'll say, one of which is clarity and I think being really clear with people around what their boundaries are and so helping them do that. The second way is we're going to use, we use technology. So like for example, we now write millions of emails using generative AI because it's just better.
David Novak
So as I understand it, Tom, you're a huge advocate, as you should be for the insurance industry. I mean, you're very involved with industry matters. What do you think is most misunderstood about the insurance category by consumers that the industry really needs to deal with?
Tom Wilson
Consumers think it's a one on one relationship when really our job is to bundle you together with other people who are like you. So you spread the losses between you. So what happens? You pay us $1,500 a year for car insurance, you don't have a loss for five years and you think we kept all 1,500 and we actually took the 1,500 and we gave it to Josh because Josh had an accident. You didn't. Most people think of their relationship with their insurers as a one to one financial relationship. When really our job is to bundle people together who have similar risk characteristics and spread the losses between you so that it's fair.
David Novak
Very, very good. You know, the insurance industry is extremely competitive. You know what makes you different from State Farm, Geico and all the others. If you're going to say, what's your competitive point of difference? What would it be?
Tom Wilson
First, we're better at math than most of the industry. We're also better at operational settlement of claims. We pay the right amount, we don't underpay, but we pay. You know, you don't want to pay too much, you don't want to pay too little. And so as a result of that, my proof would be, when you look at margins in the auto insurance business, we tend to make about four points more than the rest of the industry. And in homeowners, we make 75% of the gross profits. The whole industry loses money. Of those who make Money, we have 75% of that and we have about 8% of market share. And that's because we're really good at math and we're really good at making sure that we fix stuff for customers, but we don't overpay for stuff.
David Novak
Insurance is all about managing risk. And as a leader, what's a risk you've taken that's personally scared you?
Tom Wilson
I can't think of a first just for surgeons. General warning. I'm way out there on the risk spectrum. And so when you do those tests and stuff like that, I'm very good about, like, I always understand the facts before I make a decision what the upside and downside are. I would say the biggest risk that I took, because I think risk is important to career advancement, it was a personal risk. And I think sometimes people get confused between company risks and personal risk. Sometimes they don't take company risks, even though the company can handle it, because they have a personal risk. And I've always been willing to say, like, if it's right for the company, I'm going, and if I blow up, then I blow up. And so there are a number of those I've done and some. Some work, some don't. I would say the biggest career risk I took was when I actually came to Sears. So I was an investment banker working at Dean Witter. And Phil Purcell, who's the CEO at the time, wanted me to come work with him and do some strategy stuff. He said, you know, maybe you can run the firm someday. I'm like, oh, you know, maybe I had the chance to go into PE and be a partner at a firm with some friends of mine, and then I could go to Sears, which was not performing well. Everybody was not a darling of Wall street and everything. And I went because I saw more upside and My friends thought I was dead from the head up. They're like, you went to Sears? And I'm like, yeah, I think I can make a difference here, and I got the right tenure, and so it'll be all right. And so I think taking risk is just about being prepared, thoughtful, and then knowing what your purpose was at that time. I had our third child who's just being born. I'm like, okay, you know, I could go to work for Sears and maybe I'll have a life, or I can go to work for this PE firm and I'll have no life, but I'll make a bunch of money. So I went to Sears. Turned out I worked every day for the next year on the breakup of Sears. So I was completely wrong what it was going to do for me, but obviously it worked out because I'm very happy doing what I'm doing.
David Novak
Yeah, great. You know, and you talked about the power of AI in terms of how you're handling emails now. And, and I've, I've heard you say that you can't promote. You can't promise that AI won't change jobs, but you can promise that people will be employable. Say more about that.
Tom Wilson
So employable, for us, the definition is you can get another job relatively quickly at the same or better compensation. That's what we mean. So even if your job goes away, and so what we say to people who are working on our AI projects now is, look, this is going to happen anyway, so you might as well be on the creation of it because we'll be ahead of everybody else and somebody's going to need somebody to help do this for them. So that's what employability means. I think there's another part, David, of AI that I wish we were farther ahead on, but I think it's an issue that is for all business and could be a tragedy of the commons, which is building good jobs. So if you ask individuals what do you want from business? They don't say, I want a profit margin. They might say, I like this, the service I get. But really what they want are jobs. And if you look at what AI can do, it can get rid of a lot of jobs, particularly in a service business like ours, or if you go into some of your own business, I mean, I go to, into restaurants now. There's, you know, nobody there. I was buying some stuff at a ski place the other day. There's not even a person there with their name on the badge from, you know, you know, Boulder. And, and so it will Take a lot of jobs away. I think the challenge that business has is how can we use this technology to do things for people that they want us to do that we couldn't do before because it was too expensive. That are a job that's a good job for people. So how to create, how do you create a 25 or $30 an hour job using technology that people will pay for as opposed to. I can use technology to get rid of an $18 an hour job. We're not that good at it yet. All of our AI teams have a responsibility to do it. If I said to you, oh, here's this great success, we don't have a great success, I do think if we're focused on the customer we will come up with something we can do for them. Which is better using AI than just saying you can just talk to our chatbots personally.
David Novak
How are you using AI to make yourself a better leader?
Tom Wilson
So I have my own copilot agent and it reads emails, it does stuff, I use it all the time. I was coming to the office the other day and I was working on what we call a design, build and deploy plan. And I thought, you know, we need some sort of checkpoints. And so I was on the way to the office and I didn't have time to do it. So I used Chat GPT and I did a paragraph and here's what I'm looking for and it gave me like this 4 category 3 sub points of here's how our check ins and I just printed off gave it to our team. I said oh, Chat GPT did looks pretty good to me. What do you think they said looks good. Off we go. And you know, we might have, I might have spent two hours on that before. And you know what, we'll just change it if it's not right.
David Novak
You know, you're an extremely optimistic leader and you know I see that trade in a lot of great CEOs. What do you do to keep your energy up so you can model that kind of leadership day to day?
Tom Wilson
I try to be for one is be focused on your purpose. So know why I do this. Like I get up in the morning and I know what I'm trying to get accomplished. Two, be really focused. But three, really manage my energy. So I've always been pretty good on managing my physical energy, getting workouts, eating right, that kind of stuff. I would say in the last seven or eight years I've gotten a lot better on sleep as recovery time and necessary. So I used to go, I sleep Six hours a day. I was proud of sleeping six hours a day. And then I read this book, why We Sleep. And I come to the conclusion I'm going to get eight hours, seven to eight hours of sleep. And most days I get eight hours of sleep and I have more energy. I feel better. I'm in a better mood. The only thing is, my wife said to me, I have to tell you, I've been telling you, you need more sleep for like 30 years. Why is it you have to read 300 pages to know what everybody else knows is true? I'm like, I don't know, but I'm getting more sleep.
David Novak
Well, it sounds like I just heard about one of your real truth tellers. Your wife. Wife. You know, Tom, this has been a lot of fun and I want to have some more with my lightning round of questions. So are you ready for this?
Tom Wilson
Yep. Okay.
David Novak
The three words that best describe you.
Tom Wilson
Curious. Enthusiastic. Change.
David Novak
If you could be one person for a day beside yourself, who would it be?
Tom Wilson
The Pope.
David Novak
Your biggest pet peeve?
Tom Wilson
Self indulgence.
David Novak
Who would play you in a movie?
Tom Wilson
No, that's a good question. I don't know. Tom Cruise.
David Novak
What's the best college football game you saw this year?
Tom Wilson
The Georgia game.
David Novak
What's something you've been curious about lately that has nothing to do with work?
Tom Wilson
Trust. It's a little pushy that it's not has to do with work, but it's, it's. It's out there.
David Novak
What's the one thing you do just for you?
Tom Wilson
Exercise.
David Novak
Besides your family and friends, what's your most prized possession?
Tom Wilson
An heirloom that my mother gave me.
David Novak
If I turned on the radio in your car, what would I hear?
Tom Wilson
Either classic rock or npr.
David Novak
What's something about you few people would know.
Tom Wilson
You know, I'm such an open book. I'm really struggling with it. Like, I'm trying to think, like, what do people about me? What do people not know about me? I write poetry.
David Novak
What's one of your daily rituals? Something that you never miss?
Tom Wilson
Telling my wife I love her.
David Novak
You're out of the lightning round. Great job. Yeah. You've been in this role now for a couple decades as CEO and at some point someone else will take over the reins as CEO of Allstate. What are you trying to drive so deeply into the organization that it never ever goes away?
Tom Wilson
A belief in that we're creating opportunity for our employees and improving communities, so. Improving communities. I talk about it all the time. We have a foundation. I've pre funded the foundation so that even if a new leader comes in and they hate the work we're doing, there's enough money in there that it gives us a three to five year window out. So it's those two things, because I think we always have to be driven by customers, and shareholders aren't going to let go either.
David Novak
Now you have three kids, as I understand it. How has being a parent shaped the way that you lead?
Tom Wilson
I think I'm more understanding of different points of view and hoping that they can achieve what they want in their life. So when I first did my purpose work, I was like, look, I'm a good father. I have a good relationship with my kids, but I don't want them to make my story their story. I don't want people who come to Allstate, they have to make our story their story unless they really want it.
David Novak
And how do you go about leading at home?
Tom Wilson
Mostly follow.
David Novak
What do you mean by that?
Tom Wilson
Ask lead. Recognize your position, power. Try to meet them, what they want. So I'm a problem solver. Not all of my kids, when they talk to me, want their problem solved. And so I've had to learn to say rather than, here's the thing, they just want me to listen. They just really want me to say, it's going to be okay. They want some empathy. And I'm like, oh, we could do these things, this thing here. And so I've had to learn to not be a problem solver at work or at home. And I think that helps me not be a problem solver sometimes at work.
David Novak
How do you learn how to be a good listener? I mean, you know that that's an important trait. It sounds like that's something that you've worked on and gotten better at. I mean, what was your process for doing that?
Tom Wilson
Well, it's gonna. First I think about it, physically, I'm like, okay, I have two ears and one mouth, so I should listen twice as often as I speak. So in literally, like. And then sometimes, David, in a meeting, I'll look at my watch and I'll say, I'm not going to say anything for five minutes. It's hard for me. I'm a vacuum filler. And so I let the silence do the work. I say to our teams, let the silence do the work. So if you're in a board meeting, I tell our people, you're talking to our board. If they don't say anything, just stand there. It's going to be painful. You're going to be wondering, you've been you're on board. You know, you're going. You're going to. And you got to just stand there, let the silence do the work. So if you just can convince yourself that it's going to be okay being silent, people will say the most interesting thing.
David Novak
As you look forward, Tom, what do you see as your unfinished business, both personally and for Allstate?
Tom Wilson
For Allstate, the. My unfinished business is getting us down the path on Ally. So really embedding Allstates agentic AI into our business. And because I've been here long enough, not necessarily smartest guy. I'm a pretty fast processor, but I can see how it all fits together. So I think I have to get that done professionally. I still am. We are both. My wife, I big believers in youth empowerment. And so, like you pursuing something after a professional career, I think I will lean in more on youth empowerment and, you know, helping, because I think kids, they're not. They don't carry all the baggage we have. They're risky. And you know what? Like, they're the future. Why wouldn't we help them?
David Novak
You know, you've mentioned empowerment as a word, you know, a few times, and it's a concept, you know, and a lot of times, empowerment can be misinterpreted. You know, how do you. What's your definition of empowerment as a leader? I mean, and how do you know when to empower?
Tom Wilson
I think you're right. I agree with you that empowerment is often misinterpreted. I think the best kind of empowerment is when I'm really clear with what I expect you to do, what the outcomes are, and even how I expect you to do it and say, just don't do these other things. Here's what I don't want to have happen, and then to then trust them. I think that empowers people as opposed to, hey, go solve this problem and let me know how you get there. Like, I don't think that's what a leader should do. So I'm a. And some people think that's not the right kind of empowerment. Whereas some of my team thinks, like, you know, you just need to, like, tell me. Tell me what you need done and I'll go get done. I'm like, I don't think so. So I think clarity is really important to empowerment because it tells people what the sides of the road are. Don't go over here, go here. So I think that's really important. And then I think you have to support people when they make a mistake, go in and Help clean it up as opposed to blame.
David Novak
You mentioned trust as being one of those things that you're really learning more about outside of business. But it's tied somewhat to business. You know, what have you, where have you gone? Do you have a source or a resource that you've gone to that's, that's helped you build your capability and understanding of trust? Has there been a book you've read that you'd recommend or, you know, how are you. How are you honing that skill?
Tom Wilson
Like most things, I. I'm all over trying to get better and learn. And so I've read a bunch of books, I've talked to people. Richard Edelman has had trust barometer for 26 years. Robert Putnam wrote a book called the Upswing. I've concluded trust is a huge problem for us. Trust is down in everything. Only 20% of people believe in government. Only 30% of people believe in their neighbors. And so trust is. If we don't have trust, there's no democracy. And I also think trust is important for your own personal freedom. Like if you don't trust the Uber driver, you're not going to go anyplace if you're in a different city. So we really need to work on trust. And the thing that, as you said, I'm very optimistic. The thing that genetically I'm wired against is negativity. And the world's gotten way too negative. We looked at how much negativity there is in the world, just United States, and we took total negative minus positive and said, what kind of advertising program that be? It's $100 billion advertising program, David. It's more than the top 15 advertisers spend a year selling us stuff. So yum. And all your. All the advertising we did, hundred billion dollars of us against us, by us were just way too negative. I'm not saying we have to be Pollyannish. I'm not saying you have to. But I'm like, I think people, if you just stop for a second and think, hey, could this person be right? Can I just respect them for their having an own point of view and then be balanced about it? So I just want more balance in life and then building relationships. We need to build more relationships amongst each other, but we've gotten too diverse. The social relationships reinforce diversity. The same point of view as opposed to you broaden your perspective. If you have more, meet more people.
David Novak
Last question. What's one piece of advice you'd give to anyone who wants to be a better leader?
Tom Wilson
Constantly change yourself. There's a book written about CEOs, and it says, basically, the best CEOs reinvent themselves every four years. I bet if you look at your career, you reinvented yourself. You reinvented yourself. Now you reinvent yourself. Yum. You reinvent yourself at Pepsi. So I would say be honest with yourself or who you are. Don't let go of what made you successful, but don't hold on to it so tight that you don't do anything. So if you. If you watch people in the Olympics, the high bar and the low bar, and there's, you know, people swinging around it. Let's say the low bar is your current success. You're going to have to let go of the low bar to get to the high bar. And so you're going to go back to the low bar occasionally, but you got to let go. So I'd be like, just keep changing. Keep changing, and life will be beautiful.
David Novak
Awesome. Awesome.
Well, Tom, I knew I was going to enjoy this, and I did. I want to thank you so much for the conversation and sharing the many insights that you offered up.
Tom Wilson
Well. And thank you for helping other people and giving me a chance to be a part of your parade. So thanks,
Podcast Host
David. I can't help but just keep thinking about all the hilarious mayhem, all state commercials that I've seen over the past three months. I mean, college football is over, but I feel like I still see mayhem all over my commercials.
David Novak
Yeah, well, you know, we all have a life of mayhem from time to time, and I think they're pretty good at capturing that.
Podcast Host
I love the story he tells when the mayhem guy just tossed a piece of popcorn and hit him straight in the forehead.
David Novak
Yeah, well, you got to treat the CEO like he's just a normal guy, and he did it. And as much as they're paying that guy to do that, I bet they let him get away with flicking that popcorn.
Podcast Host
I bet they did. I bet they did. David, I'm excited to debrief this episode with you so that our listeners walk away from this conversation with some real practical things that they can apply to their life and to their leadership. And one of the themes that really stood out to me in this conversation is this topic of purpose. I love the quote that Tom says. He says it's. He says you have to enroll others in your quest to be a better person. And I just love that he also talks about having taken 75,000 employees through a process of discovering their personal purpose. And as a result of this, some people realized that their personal purpose was not aligned with insurance, so they left the company. And I'm curious, David, from your perspective, what do you do if there are people that work for you who feel like their job doesn't align with their personal sense of purpose?
David Novak
Well, first, Cole, I. I would say I really commend Tom for. And Allstate for.
For investing in their people and getting them to understand what their personal purpose is. And I think that that goes a long way for them to build loyalty and. And credibility with their team, because, as Sam Walton used to say, say, no one will care about you unless you show them that you care about them.
And I think the fact that they invested in the. The training that would allow people to really dig deep inside of their.
Their heart and their soul to figure
out who they are and what they
want to stand for and how they want to spend their time. I think that's. That's just a. Emblematic of the fact that the Allstate cares about their people.
You know, I think when people realize
that their purpose is not aligned with what they might be working on, I really always encourage people to find what it is that turns them on and go after it.
You're only on this earth once, as
people always say, and I know that's trite, but it's very, very true. So why spend your life working on something that doesn't get you juiced up every day.
Tom Wilson
Day?
David Novak
And, you know, I. I really think
that that's what makes life go, is
when you can have passion for what you do and, you know, and love what you do.
And. And when you love what you do, you're.
You're always better at it, because, you know, first of all, you're. You're usually pretty good at what you love, and then you can't wait to
learn how to get even better at it.
And you have this constant learning mindset, and you just keep upping your game
because you love it. It's like work is not work. It's your hobby. And, you know, the other point that
I really love is that, you know, a lot of leaders don't want to give people that kind of training because
they're afraid that they might come up with the.
The idea that they should be doing something else. And I just think that's such hogwash. You know, uh, you know, we.
We wrote a book, you know, on
self coaching, and in that book, you know, we have people really look hard at themselves. And, you know, a lot of times CEOs will buy the books that I write and share with their companies, but
a lot of CEOs didn't really want
to give them that book because they didn't want to go through an exercise where they're looking at what they wanted to do. They were afraid of losing their people. But I think that's a lack of
confidence and what you have to offer as a company and what you have
to offer as a leader in terms of what people can learn by working with you. So I think it takes security
to
really do what Tom and Allstate is doing. And they're confident in what they have to offer, they're confident in Allstate, and
they're confident that if they can help
people find their purpose and align it with what they do, they're going to be a far better off company. And I think it's working for them.
Podcast Host
It also made me think of how much trust the employees must have in Tom as a leader to actually go through a process like this where they discover their purpose and then they themselves have the willingness to say, hey, this isn't for me. And I'm going to trust that you mean what you say and that you want what's best for me and you want something that aligns with what I feel like I'm put on the search to do.
David Novak
And the fact is, is there are very, very few people that really say, I'm out of here, have to do in that training. You know, that that's looking at the wrong side of the decimal point, in my opinion. And, you know, but there's far, far, far more people say, hey, man, this is the kind of place I want to be, because Allstate's investing in me.
Podcast Host
David, another thing that I heard Tom say several times during your conversation is that he is brutal about his time. And what he means by that is he's brutal about his time management, and he is very disciplined about how he spends his time and who he spends it with and what he says yes to. And I want to know, David, from your seat. I mean, you were CEO of Yum Brands for almost two decades. You have a lot going on now. How do you set boundaries around your time?
David Novak
Well, when I was at Yum, it was very easy. I looked at my calendar, and I focused on three things. The three things that were critical to our company and the three things that I. I knew I had to do well if I was going to be able to keep my job and earn the right to keep my job. And so I focused my calendar around people making sure I spent the right amount of time understanding and Helping the people in our company grow. Two was customers. I felt that I had to be the chief customer officer. I didn't think anybody should know the customer better than me. And so I spent a lot of time talking to customers, going through all the research, really understanding customers, making sure we were doing the right kind of research to understand customers, and then making sure we had compelling marketing programs and operating programs to make our customers happy. So I really focused very much on customers. And the third thing I focused on was Wall Street. I was the CEO of the company. I didn't think anybody should be better at communicating our story to Wall street than me. I knew that I had to do it well, and I spent a lot of time and energy in making sure that Wall street knew our story. And I communicated proactively, and I communicated clearly, and I communicated in a way that helped, would help drive our stock price. So those were the three things. I looked at my calendar, and if I saw things getting in the way of those three things and me doing the key things that I thought were critical in each of those areas, then I didn't let it stay on my calendar. And, you know, one of the things you have to do, no matter whether you're CEO or just coming up, you have to learn when to say no to things. You have to stay focused, and learning the power of no is important. Then, as I moved on in my career and into what I'm doing right now, I went through a different process. I look back at my days at Yum, and I look back in all the time I'd spend at work, and I asked myself, what gives me joy? And then I asked myself, what takes away my joy? And I understood what the joy blockers were in my life. And I said, okay, I don't want to do any of those.
Tom Wilson
Okay.
David Novak
And then these are the things that give me joy. And that's what I was going to spend my time on, the Joy Builders. And for me, it's very clear, okay, I love leadership development. That's why I do this podcast. That's why I have David Novak Leadership. You know, I love making the world a better place by, you know, you know, developing better leaders and also, you know, helping, you know, helping people in need, you know, and helping people fulfill their potential. So, you know, we have a lot of things that we do on that front end, and I love it. I think those. Those are really great. And I love golf. You know, those were the three things. Those were my three big passion areas, and obviously my family. And so I spend Time around those, those four things. And, and that's, that's what I spend my time on. My spend time on the joy builders. And I am really good kula at saying no. Anything doesn't fit, I say no. I think you guys probably attest to
Podcast Host
that, can confirm you are great at saying no.
David Novak
But I, but I am saying yes to the things that, that, that matter most to me in my life and matter the most to others. And that's how I do it.
Podcast Host
I love that exercise because it really requires you to look inward and continue to develop that muscle of self awareness. Because if you don't know what it is that brings you the most joy, then you're gonna live a pretty directionless life just entering into all of these different things that might not add purpose or meaning or fulfillment to your life. So understanding yourself first really is the road map that helps orient you around what to say yes to.
Tom Wilson
Right.
David Novak
And I think it also leads to good energy management. If you're focused on the things that
really, you know, get you excited, you
know, you're much better able to manage
your energy and stay up and, you
know, make the most out of your day. If you're spending time on things that
SAP you, your energy goes down, you're not nearly as productive.
And, you know, it's, it's debilitating. So it's important. I, I've spent a lot of time, my life, always looking at my purpose, okay. Always looking at my navel, as someone
say, always looking in, always trying to make sure that I was, you know,
guided by the light, okay, That I have in my life.
And I, I think it's time well spent.
So I think you really have to find personal time. You have to take the time to reflect, you have to get quiet time. You know, he, I think one of
the things he talked about is, is the power of silence. Well, I mean, it's, it's not just the silence. It's in a meeting that you're having where people don't say anything because they don't agree.
It's also the silence that you can create for yourself to listen to what, what you're thinking, what others are telling you, you know, evaluate, you know, where you are in your life. You can't do that when you're hustle,
bussing, filling your, your days up just with busy work.
You know, that's why I think meditation
is so powerful, you know, you know,
taking that quiet, quiet time, finding it.
Prayer is powerful. You know, it's quiet time where you get to listen you listen to your inner voice. You listen to God, you listen to whomever you go to. You listen to Buddha, you.
I don't know, you listen to whoever
it is that you, you, you, you. You seek value from.
Podcast Host
It's so interesting you say that, David. I think I, too, am a big practitioner of meditation, and I wasn't really patient enough to practice it until someone told me that it's like dental floss for your brain. And I just envisioned meditation, like flicking gunk out of my brain. And all day we're bombarded with all these messages and all these tasks and all these things we have to do, and it just continues to build up in our heads. So to your point, if you don't take that time to listen, over time, all of that stuff just continues to build up like plaque on your teeth if you don't floss. So I think too, not only getting quiet. Getting quiet not only helps you reorient yourself around really matters, but it also helps you clear the space and kind of gets you back to this baseline of being able to determine what you want to let in and what you want to release.
David Novak
Absolutely.
And, you know, when you go to the Performance Institute, which I believe Allstate
would go to, and I actually went there with PepsiCo when I was there,
you spend time on reflection, and anybody will tell you that reflection is critical.
Podcast Host
I hope everyone listening is inspired to become brutal with their time and takes inspiration from Tom and helps enroll other people and your quest to be a better person.
David Novak
Yeah. So, Kula, I think really what we got out of this episode that I think is most powerful is, hey, you gotta find time to understand what your personal purpose is. And then you have to manage your time so that you focus on what really matters. And when you do that, you're on
your way to really maximizing not only
your career, but I think, your life.
Podcast Host
David, thanks again for another episode of How Leaders Lead, and thank you for listening. Stay tuned next Thursday, and we will see you then.
Episode #281: Tom Wilson, Chair, President & CEO, Allstate – Be Brutal With Your Time
Release Date: March 5, 2026
Host: David Novak
Guest: Tom Wilson
In this engaging episode, David Novak sits down with Tom Wilson, Chair, President, and CEO of Allstate, to explore leadership lessons learned over a storied career. The conversation centers on the value of time as a leader’s most precious commodity, the power of purpose at an organizational and personal level, and Tom’s "brutal with your time" philosophy. Tom offers candid reflections on his upbringing, leadership journey, business transformations, why Allstate doubled down on purpose-driven leadership—and how being clear, curious, and empowering is at the heart of his approach.
Childhood Values & Family Influence
“You can be a trash collector if you want. Just be a really good one.” — Tom Wilson (03:10)
Learning from Mentors
“People are the key to all success… people count. People are the be all and end all of success.” — Tom Wilson (05:34)
Brutality with Time
“I have to use it as if it really, really matters... I don’t make my time a free good.” — Tom Wilson (16:08)
Problem Solving Evolves into Facilitation
“I’ve become less of a problem solver and more of a facilitator, with a little nudge every once in a while.” — Tom Wilson (09:24)
From Vision to Middleware to Action
“How do you build a series of middleware that takes that vision and brings it down to day-to-day activity?” — Tom Wilson (14:10)
Transparency and Trust
“Allstate believes in being a good corporate citizen and that includes having transparent leaders who respect us and always tell us the truth.” — Tom Wilson (15:32)
Mascot Metaphor
Transformative Growth at Allstate
“We set off to do that…[consultants said] you’re taking on too much. But I'm like, what would you not do? ...It’s working.” — Tom Wilson (12:00)
Personal Purpose and Organizational Purpose
"If you want to be a purpose-driven company, you have to be powered by purpose-driven people." — Tom Wilson (23:49)
"Helping 75,000 people figure out what they want to do with their life…that’s really powerful." (24:23)
Courageous Empowerment
The Mayhem Commercial Story
Listening for the Silence
“Listen for the silence…if you hear nothing, you should assume you didn’t do a good job.” — Tom Wilson (20:05)
Bouncing Back from Mistakes
Clarity as Empowerment
Letting Go & Delegating
Misunderstandings About Insurance
Competitive Edges
AI, Jobs, and Employability
“You can’t promise AI won’t change jobs, but you can promise people will be employable.” (41:43)
Energy Management
Lightning Round Insights
On Leadership Style:
“Somebody once described me as somebody that wore velvet gloves but had steel hands underneath.” — Tom Wilson (01:41)
On Transforming Allstate:
“Do the hard things, do the big things. Whenever anything happens, you’ll be ready.” — Tom Wilson (13:01)
On Empowerment:
“The best kind of empowerment is when I’m really clear with what I expect you to do... and then trust them.” — Tom Wilson (51:18)
On Reinvention:
“The best CEOs reinvent themselves every four years... don’t let go of what made you successful, but don’t hold on so tight you don’t do anything.” — Tom Wilson (54:32)
For Aspiring and Seasoned Leaders:
“Just keep changing. Keep changing, and life will be beautiful.” — Tom Wilson (54:58)
For more actionable leadership wisdom, subscribe to How Leaders Lead or visit howleaderslead.com.