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Executive Leadership Podcast #194: 5 Leader Lessons from the Craziest Kentucky Derby Ever

June 30, 2022
Executive Leadership Podcast #194: 5 Leader Lessons from the Craziest Kentucky Derby Ever

The 2022 Kentucky Derby was won by a horse named Rich Strike. Rich Strike wasn’t invited to be in the race until the day before the race, after another horse had to drop out. And to add to the craziness, Rich Strike was at 80:1 odds.

When asked if he thought his horse could win, owner Rick Dawson looked right into the camera and said, “I would NEVER, EVER put a horse in a race I didn’t think it could win.”

What a GREAT truth that all leaders should be measuring themselves against. Are you putting your people into a race they have no chance of winning, or are they properly prepared to “run for the roses?”

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Perry Holley:    Welcome to the Maxwell Leadership Executive podcast, where our goal is to help you increase your reputation as a leader, increase your ability to influence others, and increase your ability to fully engage your team to deliver remarkable results. Hi, I’m Perry Holley, a Maxwell Leadership facilitator and coach.

Chris Goede:     And I’m Chris Goede. Welcome, and thank you for joining. I have the privilege of serving as an executive vice president for Maxwell Leadership. And this is probably one of the things that I love doing most, is where we get in a room, Perry and I.

Perry Holley:    Down here with the little people.

Chris Goede:     It’s just us down here talking about real life, talking about things that you experience on coaching calls or when you’re in the room consulting. You were with a client this morning dealing with trust and other things. And so this is just real talk, and I love doing this. And so I want to encourage you as you’re joining us maybe by video today on YouTube or listening to us to visit There you can learn more about the five levels of leadership, really the methodology that we use as the foundation for a lot of our culture training and coaching inside organizations.

Maybe you want to download the learner guide. You can go there and be able to do that. Well, today’s topic, and I haven’t said this in a while, but Perry always likes to throw me a curve ball and change the topics up a little bit. This one got me, and a matter of fact, our producer, Jake, we were running a little late today and he said, “Hey, I’m ready to talk about the Kentucky Derby. Where are you guys at?” So today’s topic is five leader lessons from the craziest Kentucky Derby ever. What are you thinking here?

Perry Holley:    I outdid myself.

Chris Goede:     Yes, you did. I think I know where you’re going, and I like this.

Perry Holley:    Yeah. Well, I know you probably think it was the lessons from the horse, but it’s not. I was thinking more about the horse’s leader, the owner of the horse, and his philosophy of high performance outcomes. Now, doesn’t that just leave you wanting more?

Chris Goede:     Yeah. Yeah. Now, so let me set the stage, because some of you are like, “Okay, what is the Kentucky Derby?” Or don’t know a bunch of details about it.

Perry Holley:    This probably goes down better than the Ryder Cup.

Chris Goede:     It probably goes down better than the Ryder Cup, yeah. So if we did one about the Ryder Cup, we should be able to pull one off with the Kentucky Derby. So Kentucky Derby is the first horse race that starts the quest for a Triple Crown, the three races that a horse and the horse’s team and the owner, they try to win. And it’s an affair, a swanky affair.

Perry Holley:    Very swanky.

Chris Goede:     People dress up, ladies have hats on, all kinds of drinks. And it’s hosted at Churchill Downs, a race track in Louisville, Kentucky. So this year the race was won by a horse named Rich Strike.

Perry Holley:    That’s right.

Chris Goede:     And what made this race a little crazy was that Rich Strike wasn’t even invited into this race until the day before when one of the other horses had to drop out. And so he got the invite. And what’s even crazier about this is that the odds for this horse to win was 80 to one.

Perry Holley:    80 to one.

Chris Goede:     80 to one. What that means is that’s a long shot?

Perry Holley:    Yes.

Chris Goede:     Yeah, that is a long shot. And that means if you bet $10 on this horse at 80 to one, that then you would win $818 on that $10 if this horse was to win. So it was since 1913 when it was the last time where a horse had these type of odds actually won the race. Now, that was a lot of information.

Perry Holley:    Yeah.

Chris Goede:     You gave me a lot of notes, a lot of data there. Did I get all that right?

Perry Holley:    You did, you did. So you might be questioning, so why would I bring this to a leader lessons conversation?

Chris Goede:     Yeah, yeah.

Perry Holley:    And so I tuned in, as I always do, to the Kentucky Derby, to the very last two minutes right before the race starts. And people have been there apparently all day. I actually have two guys I coach, they went. I said, “Tell me, what’s it really like?” They go, “Oh, well, you get there at 10:30, 11:00 in the morning, the race is going to be after 6:00 PM, and they drink bourbon all day.” I thought, “Okay, that can’t be good.” So I don’t know what they’re doing for the whole time.

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Chris Goede:     They stay awake.

Perry Holley:    The race was really amazing because this no-name horse who, he actually started at 99 to one because he wasn’t even in the field the day before. But he moved up. When the race started he was in the back, but he moved up very fast and he was coming up through the crowd. And it was just amazing to watch this horse make its way. But then they went to the obligatory interviews afterwards where they’re interviewing the jockey who’s on the horse, and then they interviewed the horse’s trainer. And the trainer was so just emotional he couldn’t even talk, but right next to him was standing the horse’s owner. And the network announcer just looked at the owner and said, “When you were thrown in at the last minute, did you think this was going to be a fun day at the Derby or did you genuinely believe you could win?” And I thought, “Well, that’s a fair question.”

Chris Goede:     Yeah.

Perry Holley:    You weren’t even supposed to be here and we’ll just take it for what it’s worth. We’ll have a great day at the race. And the owner, whose name is Rick Dawson, he didn’t miss a beat. He looked straight into the camera, right at that reporter, and said, “I would never ever enter a horse in a race I didn’t think the horse could win.” And I just, I had it on DVR, I ran it back, I go, “I wonder if we do that as leaders?” And so what a great truth that we could all be thinking about measuring ourselves against. Are we, are you putting people, your people, into places where they have no chance of winning, or are they properly prepared to run for the roses, is what this race is called?

Chris Goede:     Yeah.

Perry Holley:    Are you setting people up? Are you putting them even at the last minute into something you know they actually have a chance to win?

Chris Goede:     Yeah.

Perry Holley:    That’s what I wanted to talk about, was, what do leaders do? What are the leader lessons? I picked out five things that I took away from what he said. But I wonder what your take on was that.

Chris Goede:     Yeah, I love that. I had not seen that interview. And I hear often from leaders and people where they say, “Hey, I’m not jumping in unless I actually think I can, we can, they can win.” And for him in that moment to be able to say that, those are powerful words. And I love where we’re going with this. So lesson number one of the five, which by the way, thank you for using number five, is always be preparing.

Perry Holley:    Oh, man.

Chris Goede:     Okay, always be preparing. Man, they didn’t even know they were going to be in the race until Friday and the race was Saturday. But they had prepared as if they were going to be in the race, which allowed him, we’re going to talk about it a little bit later in today’s lesson, to hit some of these metrics that they were going after and that they had been working towards. And as Coach John Wooden likes to say, if you wait for your opportunity to present itself, it’s too late to prepare.

Perry Holley:    Yeah.

Chris Goede:     What this made me think about was, we have a client of ours we’ve worked for worked with for seven or eight years. And one of the things that really grabbed me about this partner of ours, that they said, “Hey, I want to create a culture where I want my team and my people preparing before the moment so that they’re ready in the moment.” And I thought, “Wow, that’s a powerful phrase. What are they doing on a daily basis so that when that turn, that opportunity comes, when that race, when somebody backs out and they call on you in a meeting or they call on you to show up and present, whatever it might be, that you’re prepared in the moment?” The other thing is, I’ve heard this statement that you are compensated now, in whatever that might be, in your career, field, your track, whatever, you’re compensated now for the work that you’ve done in the past that’s prepared you for this moment. And just like this race right here, the winnings of this came from the preparation that they had done before. So always be preparing.

Perry Holley:    Yeah, they had managed their calendar so that Rich Strike, the owner said that, “Yeah, we looked at, Kentucky Derby’s on a certain day. If we were to qualify and be in the race,” they counted back, every five weeks they ran a race. And started with, they went back 30 weeks or so. And they said, “Every five weeks we’re going to run a race to prepare to do that. And that if we did that, then if we do get the opportunity, we’ll be ready to do that.” I thought, “Wow, even looking at the calendar to say, ‘What would it take? If it were to be possible, what would we have to have done?'” And so obviously they did the right things.

Lesson two is that he said he knew what it took to win. And during the interview it was actually interesting because, it’s like if I’m looking at this camera right now, past that was the scoreboard from the Derby. And he said that during the interview he kind of got choked up when he looked past the camera that he was being interviewed with and saw the scoreboard, and he saw the winning time, 2:02. And he told the announcer, the interviewer, that he’d always told the team, “We’ve got to be focused on what it’s going to take to win this, is 2:03.”

And they kept, “Our battle cry is 2:03.” And when he went to see the jockey right before the race, he says, “Go get me a 2:03.” And I thought, “How many times do we put our team into place, do we really know what it takes to win?”

Chris Goede:     Yeah.

Perry Holley:    So that I’m preparing to that. The five weeks they knew, “We’ve got to get to a 2:03.” And kind of funny, he got choked up. “I’m looking at the time. I’m thinking, ‘Wow, we did it.'”

Chris Goede:     Yeah, man, I absolutely love that. That gives me goosebumps when I think about that and knowing that they were going after that mark and that they had this clear goal in mind, and it set up the team for success. And then for them to be able to hit that on a very important day. I think for us when our team knows what we’re aiming for and what they’re working towards, even when they’re not in the limelight, it’s not Saturday, but they’re out there running those races and they know every five weeks what they’re aiming for, that they encourage them to keep going after it, not back off, not slow down. And so as leaders we have to challenge them to do that. We’ve got to set clear goals. What is that number? 2:03, go get me a 2:03. And I love it because that’s what they were focused on. And that was the expectations of the team, to do that 2:03. So I love that.

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Perry Holley:    And lesson number three stems off of that. It was that they had this incredible belief in, you have to believe in yourself. And I thought the owner, the trainer, the jockey all had this massive positiveness about themselves and about the horse, about the conditions. They appeared to be the only ones at the track that were not surprised by their win. They were like, “Yeah, we won.”

Chris Goede:     Meanwhile, the entire world …

Perry Holley:    Yeah, the entire world was going, “Whoa, 80 to one. No way.” But they weren’t running around, “Can you believe we won? Can you believe …” They weren’t doing that.

Chris Goede:     Yeah.

Perry Holley:    They were very calm and collected, actually emotional about how their plan came to work and that they did exactly what they thought they could do. The question I have, and it’s a hard one, is how does a leader build self-belief into a team? Is that something a leader can do?

Chris Goede:     I think you absolutely can do that. And I think now more than ever that’s a skill set that as a leader you need to be continuing to work on and to practice. One of the ways that I like to do it is I like to bring up examples that I see in them that they probably don’t see in themselves where they have added value to a client, maybe a team member, maybe someone else on the leadership team. And again, I just don’t like to make general comments or general statements. “Hey, Perry, man, when you did this the other day, man, that was awesome. I had never seen anybody …” So what does that do for Perry? That’s like, “Oh man, I do belong in this room. I do have a little bit more belief because of that.”

Now, you can do it generically and make those comments, but I would be watching and I do watch for ways to where I see a team member stepping up, maybe doing some things outside of what their current job role is, and then talking specifically about what it was. It makes me think about a conversation I had a couple weeks ago with one of my team members, where I’ve seen a couple of things where they have added a ton of value to the team. And I just wanted them to know that I saw that so that then they have that belief in themselves to keep doing that.

Now, again, proper motive. I’m not just doing it so that they’ll do more of it. I’m doing it so that they have that belief in themselves hopefully not only to continue to do it inside their organization and their world here to increase their influence, but even outside of our work, at home with their family or in their community. And so I think that’s one way that I do that to help them bring up their self-belief, is to as their leader communicate what I see in them.

Perry Holley:    Yeah. I’m thinking while you’re talking about being a parent, and you can either notice everything your kid does wrong and remind him, definitely there’s coaching him there, but I can also let you know, I do this with my son a lot, that, “You have what it takes. And I just want you to know, I’m impressed by what you’re doing. I’ve seen you really … Now, a couple of areas you could work on, but wow, you really have what it takes.” And just building that, “I can do this. I can compete. It’s going to be ups and down, but I can compete.” I just love the way they talked about their belief in coming to this race.

The next one, number four, was that the leader believes in the team. So not only do they believe in themselves, but the leader expresses belief in the team. And how do I let them know what you were just saying, that it’s not only getting them to believe in themselves. That’s big, you’re really not going to go anywhere past what your own self-concept is.

Chris Goede:     Yeah.

Perry Holley:    It’s going to be self-limiting beliefs we call that, if you don’t believe you can do it. So I’m always trying to get you to believe you can do it. But as a leader, I have to believe in this team. This team, this owner, this trainer, and this horse and this jockey were a cohesive team. How do you let them know that you’re really in their corner? “I’m for you,” if we use some of our terminology.

Chris Goede:     Yeah, definitely.

Perry Holley:    What are your thoughts on that?

Chris Goede:     So for me, it’s very similar to what I do on an individual basis, but I like to do it in a team environment, to where the team hears specific examples of what the team is doing and how the team is contributing and where they’re at. And I think when you do that in a collective environment it rubs off on each other a little bit, to where even maybe some of that encouragement and that belief comes from other team members outside of those meetings. And so if you do it that way. The other thing I would say is that, make sure that when you’re in that team environment and you’re building that belief in them, you’re using specific examples like I just talked about. But also, tying back to, we’ve talked about this before, the values inside the organization, right?

So, “Hey, man, I absolutely love what this team is doing. One of our values is exceeding expectations. You guys are exceeding expectations. And man, I just want to let you know, man, I believe in what you guys have accomplished the past quarter. You guys have shown up, you exceeded expectations. I believe we can do it again.” And then that starts with whatever, the top of the funnel all the way down to the people that are delivering. And so very similar model to what I do on a one-on-one basis, but I do it in a collective environment. So that if there is something that one team member is maybe sensing from another team member, to where there’s a little bit of a downturn on their business or a little bit of lack of belief, they come alongside and they’ll be like, “Man, Perry, man, come on, we believe in you, let’s go, this team.” So just a little bit more of a collective conversation than a one-on-one, but very similar traits.

Perry Holley:    I’ll tell you one thing you do really well. You do praise results, but you also praise effort. You recognize the result for sure, but then you recognize the effort that went into the result.

Chris Goede:     That’s good.

Perry Holley:    And I’m thinking about Dr. Carol Dweck and the mindset that if we just praise results and the results aren’t there, I may pull back.

Chris Goede:     Yeah.

Perry Holley:    I may not even want to share that with you, but if I praise effort, and that leads to number five, which is always, I thought that they exhibited, and this comes from Carol Dweck in the mindset research she did, but about, they were always about improving, not proving. They didn’t come into the race for something to prove. They were in a steady stream of improving to do that. And fixed mindset, if you know about Carol Dweck and mindset, there’s fixed mindset people and growth mindset people. But fixed mindset people or teams are focused on proving to themselves and proving to others that they have what it takes. They’re proving to themselves that they’re in it.

And if they fail or if they come up short, then they stop trying. They don’t even want to risk putting it out there. But a growth mindset person really is all about trying. And even if they fail, to try again, to continue that effort. They’re not trying to prove anything to you. They’re about improving. And I think the race every five weeks that we talked about earlier, the owner was looking for small, steady improvements that were going to lead up to a big day. And that constant improving was what led to that. I thought, “Am I setting my team up or am I asking them to prove stuff, or am I challenging them to improve when they do that?” It’s interesting how they did it for this team.

Chris Goede:     I hadn’t really thought about it until you brought this lesson to us today.

Perry Holley:    That’s why you have me here.

Chris Goede:     That’s why I’ve got you here, man. That’s right. That’s why I pay you the big bucks.

Perry Holley:    That’s right.

Chris Goede:     He’s like, “I’m pretty sure I’m donating my time.” And I think there’s a bigger lesson. You’re going to hear this from us, from one of us futuristically. And I’m even thinking about even just some keynotes with clients about using this as an illustration. I love using sports examples as leadership launching pads. And so as I wrap up today, what a great leadership lesson this was. And I love the fact that if we continue to work on what we need to before the moment, we’ll be ready in the moment. And then I also think John talks a lot about preparing and repairing.

Perry Holley:    Yes.

Chris Goede:     Right? And it’s the same thing here. I think as leaders, if you’re preparing the individual team members, if you’re preparing the team as a collective, if you’re preparing processes and systems, you won’t have to be repairing them or repairing whatever, missed opportunities. Well, you have to make some deviations from the plan and some staff and some team. Yeah, all that’s going to happen. That’s part of it every day. But I think if you have that focus on before the moment versus in the moment, you’re going to do a lot more preparing than repairing.

Perry Holley:    Yeah. Yeah. Fantastic. Well, thank you, Chris. And just a reminder, if you’d like the learner guide for this lesson and see those five leader lessons, you can see that, you can also learn about the five levels of leadership or 360 Leader, other offerings that we have. You can do all that at You can also leave a comment or a question from us there. We love hearing from you, and we’re very grateful you would spend your time with us each week doing this. That’s all today for the Maxwell Leadership Executive podcast.

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