IT Leaders

One of the biggest misconceptions that leaders have is that if their team just wanted it more, they would do better. Coming from a motivational speaker. It's not a motivation gap that we have it's a skills gap and I'm not here to talk to you about IT skills. Would be way out of my depths here. What I'm talking about is frustration tolerance, flexibility, and problem solving.

Resilience skills. No matter what level you are at as IT leaders, everyone in here is a high performer, but every level has a new devil. Every level of the people that you're leaving has their own problems and everybody needs resilience. And if you had resilience, you had the mindset that no matter how hard it gets, I can deal with it, I can be flexible and I can solve this problem, that's when you get to the results you want. Because your mindset multiplies, especially as a leader.

The studies show that as a leader, your mindset affects the outlook of the people that report to you and the people that report to them. So as a leader, people that you might not even know, even interact with are affected by how you choose to show up. What your mindset is. As a baseball player, I'd say I'm an expert on mindset at this point. In my career, I hit 165 home runs and I struck out nine seventy seven times.

As you'll hear later, I also was fired from my dream job 26 times. I've moved across the country chasing my dream 56 times. Anybody move where they live? One of the most stressful points of your life. Thank God my wife is a saint.

What I have for you today are three short stories from my career with three lessons each on how to bulletproof your mindset and how to bulletproof the people that report to you's mindset as a leader. Is that alright with you guys? Awesome. My first story is from high school. I had decided when I was five years old that I was going to play in the major leagues.

This big goal. Anybody have a dream when they're five? Maybe fireman, police, astronaut, something crazy? Well, nobody ever told me I was crazy. First time I realized it was when I got to high school and I was five foot four.

Hundred and thirty five pounds. You might not know it by looking at me now but I was not a large person or a confident person. As I tried out for the high school team my running speed was so slow that the coach would taunt me by running backwards like come on come on let's go. My throwing arm was so weak that I looked like I was throwing with the wrong hand And my defense was so bad that as a catcher I was more like a dropper and a chase the baller. And let me tell you about my coach at my high school.

This was coach Matt Lacour. He was the LA Times coach of the year in California two out of my four years there. But he wasn't exactly a nice man. So when I'm desperate for this man to notice me and I'm living in my realistic limitations, I'm stuck in feeling like I'm not good enough. I feel like I'm I feel like I'm this big.

And going into my senior year he asked, who's going to hit fourth for us this year? Anybody know enough about baseball know who hits fourth? Best hitter. Not me. He asked who's gonna hit fourth this year, I'm so desperate for his attention to raise my hand.

This feels crazy because we have nine returning starters. Eight of them have scholarships to college already. I had never played on the varsity team. You heard Michael Jordan didn't make the varsity team his freshman year? I didn't make it until my senior year.

I'm not Michael Jordan either. I raise my hand and he looks at me, he crosses his arms, tilts his head to the side. And as I expect him to tell me all my insecurities, confirm them, he just says, why not you? And those three words changed my life. Because instead of worrying about him taunting me, right, running backwards, I took control back.

What can I control? Well, why not me? Even though I was the slowest guy in the field, now when we ran suicides, running back and forth, I'm sprinting. I'm sprinting. I'm hitting the line.

Even though I'm slow, I'm going fast. I'm gonna finish first. I don't look that slow inside, but outside, I'm really slow. I promise. Right?

You're doing push ups on the ground. Everybody does 10. I do 12. I do more than everybody else because that's what I can control. And by that time the season came around, I was batting fourth.

I never played on the varsity team until my senior year, and now I made all conference. What I needed was a pattern interrupt. You may have heard Tony Robbins talk about this. A guy said, hey Tony, I'm thinking about suicide. Tony says, it's probably because of your red shoes.

What? He changed the conversation. That's what my coach did for me when he said, well why not you? My conversation was all about my limitations. Now it's all about possibility.

Those three little words changed everything for me and all it took was a pattern interrupt. Right now, your team may be worried about AI, about the tariffs, the global macro economy. Right? There's something going on that they're stressing about. As a leader, how do you change that pattern?

How do you interrupt the pattern and change the conversation? Reframe it. Every negative situation has a positive opportunity. And 75% of success across all industries is determined by your ability to see that opportunity. Let me get a little nerdy with your brain science right here.

If you get go into fight or flight because you're stressed, cuts off the front of your brain. Front of your brain is where you're rational, you problem solve. If you're stressed, you can't come to a better solution. So reframe it as an opportunity. Lean into possibility.

Why not you? Maybe maybe recycle that. Use it for your team. Well, why not you? Why can't you solve this problem?

Only seven percent of high school baseball players get to play in college and because of the why not you mindset, I went from a guy that never played on the varsity team till his senior year to getting the chance to play at Yale. My mom was pumped. Pattern interrupt. Look at the other side, reframe it, and lean into possibility. If you guys have millennials that work for you, pattern interrupt.

How else can we look at this? Look at possibility. Right? I don't know how old your employees are. The next year, that 7% of high school baseball players gets to play in college.

Why not me? Got to play at Yale University. Anybody heard of Yale? Anybody heard of the Yale baseball team? No.

That's because the Yale baseball team has produced more US presidents than baseball players. That's true. My high school team ended up being ranked third in the country. Yale baseball was ranked two hundred and seventieth in division one. There are 271 division one baseball teams.

So I went from the best high school team in the country to the worst college team and that's okay because I got to play. I wasn't good enough to play anywhere else at the time. And I had another coach that changed my life with one conversation. This is coach Glenn. He went by his first name.

You'll see why. He was a little bit more positive than coach Lacour. After my freshman year, I'm thinking I'm feeling pretty good about myself. Right? Why not you?

Why not me? I saw our first baseman get awarded all Ivy League. I'm like, uh-uh. All Ivy League. Right?

I start doing the running, man. I'm like, yeah. All Ivy League. I'm gonna win it. I tell coach Glenn.

He's like, uh-uh. Why not more? If you set a goal and it's about this high of a goal, you accomplish it. Who cares? Nobody else in this room was pounding their chest when I said all Ivy League.

Coach Glenn said, why don't you win all American? There's something to be proud of. There hadn't been an all American baseball player at Yale in twenty five years, Basically, since other schools got baseball programs. But coach Glenn believed in me. And unlike my high school coach, when I felt small and he opened me up to possibility, I was feeling pretty big, feeling pretty good until coach Glenn said that and I'm like, oh no.

Anybody ever believed in you so much that it makes your stomach drop with the weight of that responsibility? He changed the way I saw the world. Right? I I was going to do something that felt so great and so impossible to me. Right?

Talk about doing the impossible. This felt impossible to me, but I decided it was going be my goal. So now I'm staying in the weight room longer. Now I'm I'm staying in class to make sure that I'm academically eligible. Right?

I started doing things that I never would have done before. Like like I I saw a weight vest in the gym. I was like, if I just wore that weight vest all the time? Every second I was awake. Would that maybe an all American might do that.

I don't know. What's it like to be an all American? So I bought a new weight vest. Wore it every second I was awake for months. What does a weight vest have to do with baseball?

I don't know. Maybe nothing. Maybe everything. Because when I took that weight vest off two months later, I couldn't just run. I felt like I could fly.

When our first game happened, I stepped in the box confident knowing that I had worked harder than everyone else that I was playing against because those idiots wouldn't wear a weight vest. Or maybe I was the idiot. Right? Every time I bent over to touch my shoe, weight vest. Tie my shoe.

Every time I got up from my desk in class, weight vest. Every time I was dancing with the coeds at the bar, right, weight vest. Sometimes it even got me some extra points because they're like, oh, abs of steel. If you want to go towards a bigger goal, need to remove the obstacles in your way. Anybody ever here gone on ever gone on a diet kick or workout kick?

You need to get the Halloween candy off the counter. Right? Or I guess get the Easter counter candy out of the pantry right now. Right? If you're going to work out at five in the morning, lay out your clothes the day before.

Right? For me, I needed to get all of the distractions out of my way because I had a goal that was so big it helped change the way I saw the world. Value tag. This is maybe my favorite one. Assign importance to the things that matter.

Only 5.9% of companies are talking about their their goals on a daily basis. But 97% of employees and executives believe it affects the outcome of everyday tasks. Where's the disconnect? If you have personal goals, how often are you talking about them? How often are you thinking about them?

How often are you journaling about them? Right? If you're not focused on your goals, it's not affecting the things you do on a daily basis. I wanted to be an all american so bad I had a weight vest on so that I could focus on it every single day. Anybody ever heard of the red car theory?

How many, how many red cars did you see on the road on the way here today? No idea. No idea. If I gave you a hundred dollars for every red car you pointed out, you think you'd notice more? Yeah.

Right? You're assigning an importance to it. You've heard of the reticular activation system in your head? Basically when you say something is important you notice it more. Right?

Like people that want to have babies or pregnant women notice more babies on the street. The same amount of babies are there for everyone. They notice it more. If you're looking to buy a red car, you're going notice more red cars on the road. The problem is that there's 5,000,000,000 pieces of information coming at our brains every day between what you see, smell, taste, hear, and touch.

5,000,000,000. Our brains are not in the IT world. Right? They're not designed for anywhere close to that kind of input. So we have to sort through what's important.

And when your goals are front of your mind, you notice more opportunities to get there. There had always been weight vests at the gym. I never noticed them before. Now that I had a goal, I started noticing new opportunities. Look around the room.

See how many things you see that are blue. How many things do you see that are blue? Alright. Indulge me for a second. Close your eyes.

How many things did you see that are green? You can open them. The cup in front of you is green. Did anyone notice it? Right?

If you're not looking for it, you're not gonna see it. If you're not focused on your goals, you're gonna miss opportunities to get there. So what will you value tag and what will you ask your team to value tag? Right? This isn't about me and baseball stories.

I'm not interested in a memoir. I'm here to help you help your team. What do they need to value tag on a daily basis to get to your goals? I'm sure you already know what it is. Last thing with this why not more story.

You need to embody the person that does the thing you want to do. Right? It's not good enough to try to get straight to the end. You have to do the work to get there. With that in mind, was telling this this story so often and I felt like I wasn't walking the walk anymore.

So I've started I've started doing this speech with the weight vest on because I believe that this weight vest has the same to do with speaking as it does to do with baseball. Maybe nothing. Maybe everything. Because you're gonna remember the guy that talked with a weight vest on the whole time. Right?

It may not look like much, but it's that little extra effort that gets you hired, that gets to the product, that does the impossible. That little extra that you can do that makes you special, that makes you stand out. How do you get your team to find their version of the weight vest? And it doesn't have to be a weight vest. Only nine percent of college baseball players get to play professionally.

We had seven percent of high schoolers. You guys are probably way better at math than me. 7% of high school players, nine percent of college players. After my junior year, after winning All American, which was my goal, winning the national battle batting title and slugging title and breaking 14 records in the Yale record book, I got drafted by the Boston Red Sox. The thing I didn't notice about that is that only 16% of players that get drafted to go pro play one day in the big leagues.

Seven percent, nine percent, sixteen. The average minor league career is only two seasons and an off season, so twenty one months. Over the course of that time, players take 33,000 swings, 19,000 throws as a catcher, catch 12,000 pitches. You throw your body in front of 5,000 balls. Think about if you focus on your goals 1% more for 33,000 swings.

Think about if you did it better 1% better 33,000 times Because you've got to climb up all these letters. Right? You played little league. You played in high school. You made the varsity.

You got to play in college. This is where you start when you get drafted. There's still a long way to go. So I decided why not me? Why not more?

In the minor leagues, I saw somebody my first year get awarded minor league player of the year. That's my goal. And I won minor league player of year three years in a row to get myself called up to the Boston Red Sox. And if this TV was bigger, Doug, my arm looks real big on a big screen. We talked about the need for resilience.

When I got to the big leagues and my dreams came true and my family flew out and I'm on SportsCenter and I'm so excited and my first paycheck was pretty nice, eight days later, I got sent down to the minor leagues. Eight days later hitting three zero five. I don't know who knows baseball. It's pretty good. Minor League Player of the Year three years in a row.

It's my turn to shine. No. David Ortiz was healthy. Anybody know David? Big Poppy?

He just made the hall of fame last year. I didn't make the hall of fame. Not that one. I told you I got fired 26 times. I lived in 33 cities in this country.

I wore 28 different my, uniforms, Major League and Minor League. Sometimes I was on a team for such a short amount of time, I didn't even get a headshot. This was before AI could do it. Once my dreams had come true, I learned that you can only go so far on your own and then you need a good team around you. You guys can only go so far on your own.

You need your team. You need your staff. At the risk of violating SAT protocol, I'm going to define this with the word in the definition your emotions are contagious. You've experienced this before. If I walked up here and I was speaking and I was like, Hey guys, I'm Ryan.

Right? It would set a different tone right? Even with the weight vest. I'm here. I'm energetic.

I see smiles out there. I'm getting smiles back. I appreciate it. Right? If you show up for your staff in a good energy, good mood, it's going to spread.

Same with resilience. It only takes thirty three milliseconds to read, understand, and begin to take on the emotional state of someone else. The human brain is amazing. The best teams that I was on knew this. This is team chemistry.

I'm only going to talk about one of them because I have a short time The Boston Red Sox. Two thousand twelve, we were called an unmitigated disaster. We had three managers in three years because we were so bad they kept firing our manager. That next year we won the World Series. It's Ryan right there.

Best beer I can grow. What was different about this team? We leaned into the why not us mindset. Right? We had another player that held a team meeting, Ryan Dempster.

He told us we were going to win the World Series because of the three F's. First F fundamentals. Don't be too good to do the small things. If you do the things that matter every day, you will win. Foul tips.

This is a baseball term. Pitcher pitches it. Hit or swings, they just barely touch the ball. Ball's still going backwards. Okay?

You with me? Sometimes the catcher catches it. Sometimes the batter's out. Only sometimes. It's a very weird rule.

The point is that how do you take advantage of your opposition's near miss? Right? Everybody has competition. Everybody has competition. How do you do it a little bit better?

How do you take advantage of every tiny opportunity you get? Third f, four run homers. Who knows what a four run homer is? Everybody knows. This is a great group here.

Why do you call it a four run homer? It starts with an f and fits the motif. Right? Why else did he call it a four run homer? Right?

He gave us words that meant something to us, an idea that meant something to us even if it means nothing to anybody else. What do you guys call that? You guys call it mission, vision, and values. Right? I compared the other stories to a fictional character.

He was like Bugs Bunny. He really wants to be Michael, but he was like Bugs Bunny because he shared the secret sauce, the secret stuff. We had those three f's and when we were down one nothing in the American League Championship Series we were down we were down one game to nothing we were down by four runs this happened. Remember big poppy from when I got sent down the first time? Lord giveth, Lord taketh away.

You see when he touched on plate? Four on homers. Four fingers. He's not thanking gracias adios right now. Four on homers.

Right? And in the dugout, do you think we're saying? He just tied the game. Didn't give us a lead. Tied it.

In a series we're still losing. Guess what? We're like four on homers four on homers four on homers four on homers four on homers. We're gonna win. We know we're gonna win.

What's the language that you use with your team that you know you're going to win even before you get there? What happens where you know you're going to win? It matters to you even if it matters to no one else. As a leader, what energy do you want to bring to your team? What do you want your superpower to be?

Because even the drill sergeant changed my life. You don't have to be positive. There's more than one way to lead. Your disposition is more important than your position and you should lean into your authentic style. I've partnered with a woman here in Denver to do leadership training.

It's an amazing program and the people that we work with, the first thing that we do is we lean into figuring out what is your unique superpower. How are you going to lead before we get into any other concepts? Pattern interrupt, reframe, possibility. You're gonna see that that pattern every time. It's very consistent.

The x, the turnaround, the lean into possibility. If you want to get bigger goals, remove obstacles, value tag, and embody the person that does those things. And as a team, do the fundamentals. Catch your foul tips. Hit your four run homers.

As you're gonna leave here today, remember that information without action is stagnation. If you don't do anything about it, it doesn't matter. Information is great. You need to do something. Information with application is transformation.

Hopefully, you took a lot away from this. If there's if you only took one thing, hopefully it's action. Right? You don't need to change everything about your leadership style. You only need to figure out what the first next step is.

Every time that I was working towards my goal of getting to the big leagues, felt like I was taking a little step. Right? I made the eight year old All team, made the 10 year old All Star team, made the 12 year old All Star team, made the freshman team, then I made the sophomore team. Junior varsity. Right?

Got to play in college. Got called up. Oh, I got sent down. Right? There's a step backwards.

Got called up again. Get sent down. Anytime you get pushed back and you're way towards your goal, just take that next step. I could have been brokenhearted. I could have crumbled.

Anytime that you get pushed back, you have the opportunity to take control back. What's the one thing that you can take control back and keep moving forward? Why not you? Why not more? Why not us?

And why not now? Thank you guys.