Start With A Win - The Blueprint for Building an Unstoppable Team / Mike Erwin

Episode Date: June 4, 2025

⚡️FREE RESOURCE: 𝘞𝘩𝘢𝘵'𝘴 𝘞𝘳𝘰𝘯𝘨 𝘸𝘪𝘵𝘩 𝘠𝘰𝘶𝘳 𝘓𝘦𝘢𝘥𝘦𝘳𝘴𝘩𝘪𝘱?  ➡︎ https://adamcontos.com/myleadershipWant weekly leadership content? Go here ➡︎ https://adamcontos.comIn this episode of Start With a Win, host Adam Contos welcomes leadership expert and combat veteran Mike Erwin for a compelling conversation on what truly separates great leaders from failing ones—often without them even realizing it. With a rich background spanning military service, Fortune 500 consulting, and in-depth research on leadership psychology, Mike dives into the game-changing power of relationships in leadership. He challenges the transactional mindset, emphasizing the need for connection, the a word no one wants to talk about, and setting the bar high to unlock untapped potential. Packed with real-world stories and powerful insights, this episode is a must-listen for anyone looking to elevate their leadership game and build stronger, more resilient teams.Mike Erwin is a dedicated leader and founder of The Character & Leadership Center, working with organizations like Amazon, the Boston Celtics, and the U.S. military. He co-authored Lead Yourself First and Leadership is a Relationship, emphasizing solitude and relational leadership. A West Point graduate and former Army Intelligence Officer, Mike served in three combat tours, earning two Bronze Star Medals. He also founded Team Red, White & Blue, supporting veterans’ health, and co-founded the Positivity Project, which reaches over 500,000 children daily. Mike continues to serve as a Lieutenant Colonel in the Army Reserves.00:00 Intro02:15 Four intense years of leadership!03:59 Leadership, is it a relationship?06:35 Leadership is not this, management can be.08:15 The big A word!11:19 Can you get over the high bar? 13:40 The T word and being consistent with it!18:25 Dueling Pianos?22:32 Massive leadership impact…27:01 I thank this person and straight into this… https://characterleadership.center/===========================Subscribe and Listen to the Start With a Win Podcast HERE:📱 ===========================YT ➡︎ https://www.youtube.com/@AdamContosCEOApple ➡︎ https://podcasts.apple.com/us/podcast/start-with-a-win/id1438598347Spotify ➡︎ https://open.spotify.com/show/4w1qmb90KZOKoisbwj6cqT===========================Connect with Adam:===========================Website ➡︎ https://adamcontos.com/Facebook  ➡︎ https://facebook.com/AdamContosCEOTwitter  ➡︎ https://twitter.com/AdamContosCEOInstagram  ➡︎ https://instagram.com/adamcontosceo/#adamcontos #startwithawin #leadershipfactory

And this is where great teams and great senior leadership teams are built, where everyone or most of the people on that team, you know, really trust each other and they consistently show up for one another. When you don't know the people who are working for you or with you, then it becomes very transactional. And my argument on this is that leadership is not transactional. Management can be transactional at times, but leadership is not, it's relational. This word just jumps out to me

when you talk about full contact leadership and how we can and can't have it based upon those relationships. That word's accountability. What does that mean to you and relationships and leadership? Welcome to Start With a Win, where we unpack leadership, personal growth and development,

and how to build a better business. Let's go. What's causing leaders to fail and they don't even know it? Today, we talk about that on Start With a Win. Coming to you from Area 15 Ventures and Start With a Win headquarters, it's Adam Contos with Start With a Win. We're diving deep into that topic with a special guest

who not only studies leadership, but lives it every single day. We've got Mike Erwin, the founder and CEO of the Character Leadership Center and co-author of Leadership is a Relationship. Mike is a West Point graduate, a decorated combat veteran with three tours and holds a master's degree in positive psychology. He's not just talking about leadership theory, he's been on the battlefield and in the boardroom applying these principles. He's worked with everyone from Fortune 500 companies like Amazon and PWC, to the Boston Celtics and Special Forces units.

Get ready to hear some amazing stories and insights on why putting people first is not just a nice idea, but a game changing strategy. Mike, welcome to start with a win. Hey, thanks so much, Adam. Fired up for the conversation. Right. First of all, I want to say thank you for your military service and all you've done for our veterans.

I know you do a lot of work both with West Point as well as different people in the United States to help grow leadership and ensure our veterans are in a good place. So why don't you take us back to how you started in leadership? Because you have a really interesting background graduating from West Point and even teaching there, things like that.

Give us a flyover of your leadership experience and how you got to where you are today. Yeah, so for me, it started when I was young. I had a former Marine who was my little league baseball coach, Tom Nylons. And the seeds were planted young between my parents and then playing sports and having mentors in my community on my paper route.

I used to deliver papers every day for five years. So you meet lots of interesting people. And I think that's where the seeds were planted young. And yeah, it really manifested at West Point when I applied. And I went to the US Military Academy at West Point and I joined the Corps of Cadets. That was four intense years of leadership development. Then really since then, in many ways it's been a bit of a blur, but the major turning point for me was when after my third

combat deployment, the Army selected me to go back to grad school and I studied leadership, resilience and positive psychology at the University of Michigan. And then I went back and taught leadership and psychology at West Point. So that was really some of the major stops along the journey, but from a younger age and then in the military and then really getting a chance to study it for two years as a grad student and then go teach it. That's awesome. I'll tell you, I had a paper route too. There's nothing like the discipline of getting up early in the morning and folding these papers and putting rubber bands on them or in bags

and delivering those bad boys every single day. That'll build some resilience and grit in you. Yes, it does. Let's get into, you authored a book called Leadership as a Relationship. And it's not often you see those two words together, but they mean so much together. And I think this is really important.

It's going to be the foundation for so much that we talk about today. Why did you write that book? And what does the title mean? Yeah, so it actually started from my time in grad school that I just referenced. So 2009 to 11, so for two years I was a grad stool. And in positive psychology, what we learned

was that the number one driver, the number one predictor of life satisfaction is the quality of your social relationships in life. So family, friends, teammates, co-workers, neighbors, roommates, the people that you do life with. And so I actually wrote a paper in 2010 as a grad student called Leadership as a Relationship. And that was really an exploration of the relationship

often that people feel between themselves and like their political leaders or like leaders in their country. And that was like where the beginning of the process started for me. And then I went out and co-authored my first book called Lead Yourself First. And so I went out and co-authored my first book called Lead Yourself First. And so that came out in 2017. And I thought for sure, hey, one book, that's it. Then during

COVID, you know, there was a lot of time, not traveling and a lot of time to sort of reflect and think. And I realized, you know, a lot of people have been asking that question, hey, you're gonna write a second book. My answer was always no, no, I contributed to one book and that's good. And then I realized that there was an opportunity, especially during COVID when we saw all the physical distancing and the separation of people and the realization that, hey, as life starts to resume and to look like normal again, whenever that was going to be, that there was going to be a real need to help leaders think through the role that relationships play in a post-COVID world.

Because a lot of people had been conditioned over a two-year period, you know, to kind of be afraid of people and to be separate from people and to work remotely all the time. And to me, it became a really interesting question to explore during COVID of, hey, as a leader, how do I need to ensure that I am continuing to prioritize the relationships I have with the people on my team, the people that I am continuing to prioritize the relationships I have with the people on my team, the people that I lead, so that I can be the best leader and the best teammate that I can possibly be.

Do you think, and I mean, you mentioned a few things there that actually kind of crash into each other. Obviously COVID and relationships immensely crashed into each other, especially with this, you know, this remote work environment. And I know we're going through this discussion, like with the federal government of remote work. And a lot of people are like, I don't want to go return to office. But all the leaders are going, you need to be face to face with people

in order to be able to lead them and have those relationships with them. What do you think one of the biggest implications to that conflict were during COVID? I mean, did you see any tangible declines or anything like that when it came to leadership and relationships because we weren't face to face? For sure.

I mean, I heard this a lot from and had the chance to work with leaders from lots of different companies, larger companies, down the small ones here locally. And people would say often things like, hey, you know what? I'll be honest with you. I just can't really be empathetic for this person on my team, who is not doing that great of a job. Because I've never met him. I don't even really know him. So you heard this over and over again about when you don't know the people who are working for you or with you, then it becomes very transactional. And my argument on this is that leadership is not transactional. Management can be transactional at times,

but leadership is not. It's relational. And that's a big part of what separates leadership from management is that leaders get into, and maybe not as much from your time in the Marines, mine in the Army, where we call it full contact leadership, where you're expected as the officer of the senior NCO to go check on your soldiers' barracks and see how they're living.

That's full contact leadership. So that might be a little bit too much for the civilian world, but geez, to not know anything other than maybe where someone went to school or where they're from and what their job title is. And hey, here your goals are, like when there isn't that understanding of them as a person, it's really hard to get the best out of them. And it's hard for them to feel any sort of desire to do more than kind of the bare minimum for you. Right. That's that's fascinating. And you talk about full contact leadership, this word, and I know it's really, I

think it's chapter one in your book, this word just jumps out to me when you talk about full contact leadership and how we can and can't have it based upon those relationships, that word's accountability. What does that mean to you and relationships and leadership? So this is a big one that a lot of people are talking about this right now

because this is the thing that I think not a lot of people want to address. And that is the reality, especially in a largely remote work environment, I think not a lot of people want to address. And that is the reality, especially in a largely remote work environment, where there's a lot of people who kind of do the bare minimum. And so they're questioning like, Hey, how do I hold somebody accountable? We don't want to lose them. I want to invest in them and help them to grow and help them to contribute more

to the team, but boy, is it tough. So for me, accountability really is about the capacity and the ability for a leader or a person, because this can be, again, for parents or a whole bunch of different walks of life. But how do you, as a teammate, but especially as a leader, let people know that you have high expectations for them and that when they're not meeting those expectations

or they fall short of them, that number one, it's okay, you're not perfect. But number two, it's also not okay because I want to help you get better and I want our team and our organization to get better. And so to me, it's those tensions there of acknowledging that unless someone keeps making a mistake after mistake after mistake, or they cut corner after corner, then maybe that's a character flaw. But people are going to make mistakes.

And increasingly, again, it's a human skill to be able to hold somebody else accountable in an effective way. I mentioned this before, but the idea of I'm going to hold your feet to the fire. Well, that's not a really good image of holding somebody accountable. That's not what it's about. It's about elevating their expectations for themselves, letting them know that high standards and high expectations are a product of what we do here. And you're going to not hit those standards sometimes. But when you don't, I'm not going to turn a blind eye. We're going to have a conversation about it. We got to figure out, okay, next time, what can we do differently? How can I be better for you? How can you do things differently or better so that we meet those high standards, not just for one another, but for the team.

I love that. And you're talking about high standards here. A lot of people come in with minimum standards in their different businesses. And I think we kind of fell into that during COVID where, you know, it was, here's the minimum expectation of you was I heard that a lot, unfortunately, where I come from the world of, and as do you, hey, let's set the bar high and see if we can get over it. Even if we don't get over it, we're going to get darn close, so we're going to be way above this minimum necessary.

And it takes me back to a statement that a friend of mine who was a senior enlisted in the Air Force, retired as a senior enlisted in the Air Force, and he said, if you set the bar high, people will do everything they can to get over it. And a lot of times they will. If you set the bar low, they will do everything they can to get under it. Yeah. And I mean, yeah, it's nuts. And I'm thinking to myself, I don't want people trying to get under the low bar in my business. Give me your perspective on how do we set the bar and how do we through these relationships, help people understand that they can try really hard and get over that high standard versus just being mediocre or less. So I'm a huge believer that people, most people are not really aware

of their full potential. This has been something that I've learned myself often through ultra running and endurance running. I just ran the JFK 50 mile or a few months ago. Now I've done it five times in my life, but when I was much younger, so I'm 45 years old now. It was different, a lot different as you might expect running it as a 44 year old versus a 31 year old.

But it's just this idea that our brain will do a whole lot to put us in and tell us that we can't do something or this is going to be too hard or that's too high of an expectation. Like our brain is really good at trying to do that. And I'm not exactly why, sure why it might be, you know, just some of the self-talk and the way that our brains work trying to lower the expectation so that we don't do something. But bottom line is, yeah, we know it.

We see this in sports all the time where teams will play to the level of their competition frequently and we are products of our expectations. And so for me as a leader and going back to relationships, this is where I think it's so big. When you have a relationship and you build a relationship with somebody, you can elevate the expectations, you can raise the bar on them. One, first of all, hopefully in the relationship, you're kind of wanting, both of you are wanting to raise it together. But if you don't have that situation and you have to be the one to raise that

bar and raise the expectation, then that person hopefully is going to say, okay, you know what? That feels like it might be out of reach, but I'm still going to pursue it because I don't want to let this person down. Why? Because I have a relationship there. And it goes back to that whole conversation around transactional versus relational leadership is relational. And when you have that relationship, people are much more likely to strive to clear that high bar because they want to make you proud. They don't want to let you down. Awesome.

I love that. There's a big currency in leadership that I think is absolutely necessary, and I think you would agree with this. And that is trust. It's one of the mid chapters in your book. Take us through your perspective on trust and how it plays into the relationships

and in how leaders with and without trust vary. I mean, what does that do for us to get more out of the people that we're leading? So trust is another big one these days. I think that a lot of people are talking about and largely because, well, I think there's a couple of things to say about trust. First and foremost, I think that every time we drive down the road, we trust that the people on a two way road, right,

are paying attention and they're staying in their lane. Right. So there's this there's this trust that we have implicitly with people as we go out and live life. And that's that's not really the kind of trust that we're talking about here. When we talk about leadership, we're talking about a kind of personal trust or interpersonal trust. And so when I look at how long does it take to build trust with somebody? I mean, often you've probably heard this phrase before, but trust,

you know, is built in drops and lost in buckets. It often takes a lot of interactions, a lot of conversations for someone to really get to know you and to know your heart and to know your motivations and why are you pushing in this direction or why are you doing something? And so I think that's the struggle. We live in an instant gratification world

and we want to accelerate trust. And hey, how can I build trust as fast as I possibly can? I hear that question a lot, especially with the high turnover rate in the job market and people coming in and coming out so frequently. People are like, hey, what can we do to accelerate trust? It's hard. It's really hard. Just like relationships, they take time, they take energy. And yes, they can be broken or lost by the bucket full when you do one thing to violate that trust. So for me, I keep coming back to this idea that the foundation of trust is relationships. It's also of course, yes, consistently seeing somebody do what they say they're going to

do. So when someone says, I'm going to get this done in a certain period of time, they get it done in a certain period of time, they get it done in a certain period of time consistently. But ultimately, I do think that, you know to wonder, which obviously degrades trust. And we all know that leadership is not a sometimes thing. It's an all the time thing. Tell me about consistency. Why should we be thinking about that in building our leadership and relationships?

Yeah, consistency is so huge. We know this from people who study finance. And you know about the compounding effect of money when you study Warren Buffett and how he has made all this money. It's in the consistency. I'm trying to pull up here. I saw a great piece on this just the other day. If I can find it, it's just so good. Consistency compounds while occasional brilliance fades. Oh's just so good. Consistency compounds while occasional brilliance fades. Oh, I love that. Right? Great outcomes are not built on great days, but they're built on consistent ones. You can't just count the days when it's easy. Each day moves you closer to the

goal. No day is a hero. No day is a villain. Right? That's Shane Parrish, phenomenal author and podcaster. That's to me is the bread and butter of it right there. This idea, Jim Collins, my mentor talks about the 20 mile march. Hey, the sun is shining and the wind is at your back and it's beautiful out. You march 20 miles. The wind is in your face. It's raining and sleeting and the footing is terrible. You march 20 miles. It's the idea that you can't just like, oh, well, like, oh, it's great weather. I'm gonna go 30 miles today. Or, you know, the weather's terrible. So I'm gonna sit today out, right? Like the idea of sitting those days out, it adds up, it compounds. And so again, with our relationships and our interaction, there's a consistency there.

And there's a compounding effect. The more I interact with you, the more we have a conversation about topics, the more you get to know me, the more I get to know you, right? The compounding effect of that is powerful. And this is where great teams and great, you know, senior leadership teams are built, uh, where everyone or most of the people on that team, you know, really trust each other and they consistently show up for one another. That's awesome. And for those of you looking for some good reads, uh, you know, the compound effect by Darren

Hardy, an incredible book, he's a great friend of mine. And I'll tell you what that is, that's timeless when it comes to understanding how to create great impacts in your life. Also, Jim Collins, good, good to great and great by choice, some incredible books. I love the 20 mile march that you reference referenced the race across Antarctica. And I'll tell you what, inconsistency got that team killed.

So there's life and death at stake here. Some great information, Mike. I love it. Let's talk a little bit about this whole idea of coalition building. You talk about coalition building in your book. I think that's really important from pie in the sky to history, the idea behind that.

What does that mean? A lot of people think leadership is them leading their group, but it seems like, no, you're gathering resources to leverage leadership here. So how does that all play together, and what can we learn from that chapter? This is a fascinating topic to me, because I've seen it in my own life, my own journey, and I've sort of thought through it.

So you kind of have dueling pianos. One is this idea that we need buy-in. And as a leader, your job is not to tell people what to do, right? It's to kind of point them in a vision and then watch them, you know, kind of with creativity and all these skills, these human skills come together to do something amazing. And then there's on the other pole, there's this idea that leadership is not likeorship and that, you know, sometimes as a leader, you got to be willing to be unpopular. You got to be willing to be hated even.

Right. Um, cause at times that's, that's what the situation calls for and demands. And so for me, like the story that we profiled Mike Sullivan, um, this was in 2009 in Afghanistan and we were deployed with the Brits and the Romanians and the Canadians and the Dutch, and we had all these different, you know, elements of NATO that were deployed and we worked with them and specifically in the Helmand province, it was one of these situations where we knew that we did not have authority to go in there and to execute this big mission, which ended up be calling Operation Siege Engine in May of 2009. And so he had to build a coalition.

He had to talk to the Brits and the Brits were skeptical at first. So why do you want to do this? And he had to talk to different leaders and different people and different folks within the DEA and the Afghan special forces. And you had to kind of align and get everybody behind the idea. And so again, coalition building in that regard is more on the buy-in side. And it is saying, and this is my belief, Adam, on this is that most of leadership is earning buy-in. There are moments in times when you need to know that I don't have time for,

and I don't need the buy-in right now. I need to make a decision whether people understand why I make that decision or not. I need to be decisive right now. But where you have the time to be able to build consensus and to be able to get other people's opinion and their feedback makes a lot of sense. And so that's the idea. And the argument is that through relationships, you're able to then build consensus more because people will realize that,

oh, you're asking for my opinion. I know you're not always gonna take exactly what I say, but you're asking for my feedback. I feel more bought into what we're doing here. And again, the argument is that when we have relationships, when we invest in relationships, we get to know people beyond just their job title and their decision-making authority that positions us to then be able

to get them to understand where we're coming from and to trust us that we're coming at this for the right reason. Wow. That's powerful and I think incredibly impactful. For everybody listening, look around your organization and look around your industry, the associations you have, and how can you rally those associations in order to build those coalitions.

So this is really fascinating, Mike. I encourage everybody to check out Mike online. Mike's website is characterleadership.center. And you have a whole bunch of different websites, which what's the best one to find you at? Is that it? Yeah, that's that's a good one. And Mike Erwin dotnet. Oh, there we see like from a standpoint of like seeing and engaging and you know, and seeing more about this is on my LinkedIn. That's where I sort of update the most. Awesome. You've got some very current and very pertinent leadership

information. I have an interesting question for you. We all have this memory as we progress in our leadership lives, I guess. And we end up having a conversation at some point with a key mentor, a key leader, somebody who makes a massive leadership impact on us. Do you have a story about a massive leadership

impact that was made on you that you could share? Oh, yeah, so many. This is the thing. We are often the product. This idea of we stand on the shoulder of giants, we are the product. If we ever go on to accomplish anything significant or great in leadership, it's because of the people that we've learned from, the mistakes that we've made along the way. I remember when Colin Powell came and spoke at West Point in 1998, he talked

about how he lost his pistol on his first week as a platoon leader in Vietnam. And it could have been a fireball offense. And his commander basically was like, look, you can't do this. I should, you know, I have the authority to basically just send you back and you would be discharged. And he said, but I'm not going to do that. Like, I know you made a mistake and now it's up for you to be focused and make sure you don't make that mistake again and lead your men well, right?

And like you see, and then he goes on and had this just prolific, incredible career. So, there's so many of them in my life from my time, as I mentioned, playing baseball growing up with Coach Nyland, Coach Dodder, my high school baseball coach, just passed away this year, I think at the age of 89, was phenomenal, deep, deep philosopher. He would ask questions of us when trying out that had nothing to do with baseball. Like how much does airway? He just wanted to use like a psychologist. He just wanted to see how you thought about things. My time in the military had some incredible commanders and leaders that I saw lead. I studied them and I paid attention to them.

So I'd say my military career, my battalion commander, you know, in third special forces group, Lieutenant Colonel Don Bolduc was big. He really talked about the, you know, the window in the mirror. When things go right, you look out the window, who can you point to? Who can you give credit to? And when things go wrong, before you start looking at other people, look in the mirror. But from an intellectual side and an inspiration side, Jim Collins was it in 2012 and 13. I worked with him eight times when he came to West Point when I was a major. And I was basically his general officer type planner,

for lack of a better term. And the conversations we had were just unbelievable. And for me, one of the big things that I took away from it, there was a pivotal moment for me was he said for people who pursue greatness over their lifespan, the greatness starting line is age 50. Because I was 34 at the time and I was like, geez, I feel this sense of pressure and like, hey, if I want to run for political

office or if I want to do this or do that, I've like, I've got to go, go, go, go. And it was just this this this message of consistency. No, be consistent for, you know, your whole life. And it's amazing the opportunities that will open up before you to transform and to do something really great. And to think of your starting line at age 50 versus age 32, which I had in my head at the time was a life-changing thing for me.

I still have a sense of pressure and urgency to act now, to lead well now, but I'm still making mistakes. I'm still learning as I go. And as I look at it now, I've still got five years to the start line for my greatest contributions to the world. And to me, that was just transformational. That's amazing. Great stories there. I appreciate you sharing them, Mike.

And Mike referenced Standing on the Shoulders of Giants, which is an incredible way to look at life. It was actually a quote attributed to Isaac Newton in 1675. It said, if I have seen further, it is by standing on the shoulders of giants. And it references the buildup of the talent and the experiment and the scientific principles and whatever

have you that people before you have laid on the ground that you're climbing on top of. And it's their thoughts and their leadership that you're standing on top of. And it's their thoughts and their leadership that you're standing on top of. So really a great way of looking at, how do I become a better leader? Find those giants and learn from them. It's just a great way of looking at it.

Mike Irwin, you're a huge contributor to the leadership space. We really appreciate you. I have a question that I ask all the great leaders on Start with a win. And I know you have, I'm sure a fantastic answer. A lot of military guys have something, you know, relatively similar, but just amazing when it comes to this. But my question for you is how do you start your day with a win? So practically, I talk about this a lot. I start my day with a win. So first thing up is I get out of bed, right? And I'm like cradle Catholic. So I thank God for a good

night's sleep and for the day before me, starting the day with gratitude right off the bat. And then I parlay that into 15 pushups. And then I immediately go downstairs and I've got a series of chores that I do, kind of like Adam McRaven talking about why it's important to make your bed in the morning. I'm at the dishwasher, I make the coffee, I start cooking breakfast and I'm just knocking out tasks. Right? So after gratitude to God and a little bit of physical activity to get my blood going, it's about knocking down those little wins because it builds motivation and it makes

you feel like, all right, I'm in control this day versus it's in control of me. I love that. Everybody make sure you check out Mike online. Also pick up his book, Leadership as a Relationship. And also Mike does a great deal of consulting for different businesses and speaking of leadership. So check him out if you're looking for really a great person to deliver some actual boots on the ground experience

when it comes to leadership and, you know, growing people and businesses. Mike's a great guy for that. Mike, I appreciate all you do. Thanks for your service to our awesome country. And thank you for starting your day with a win. Thanks so much, Adam. Love the conversation, man. Appreciate it.