A Bit of Optimism - The Leadership Advice Nobody Follows (But Everyone Should) with Top Leadership Expert Don Yaeger

Episode Date: April 21, 2026

The most successful leaders, coaches, and teams in history share one counterintuitive secret: their main focus wasn’t winning. And yet… they won more than everyone else.  My guest, Don Yaeger, learned this lesson from his mentor: legendary college basketball coach John Wooden. Don is one of my favorite master storytellers, a top business leadership coach, author of 44 books, 13 of them New York Times bestsellers, and a former Associate Editor at Sports Illustrated. Don has worked alongside the greatest athletes of our generation: Michael Jordan, Serena Williams, Michael Phelps. But no relationship shaped him more than the 12 years he spent as Coach Wooden's mentee. Whether or not you're a sports fan, I promise you: the lessons Don shares are as universal as it gets. We explore what it really means to win in business and in life. The greatest leaders in history already figured this out. The question is why the rest of us aren't following their lead. In this episode you'll learn:  ➡️ Why the winningest coach in college basketball history never talked about winning (and what he focused on instead) ➡️ The Bill Walton story that reveals how great leaders hold standards without exceptions (even for their best people)  ➡️ How one conversation with John Wooden transformed Don's marriage & the weekly habit he's kept for 16+ years  ➡️ What Delta CEO Ed Bastian's "virtuous cycle" can teach any leader about putting people before results  ➡️ What a great mentor actually look like and how to know when you’ve found one If you've ever chased the short-term win at the cost of the long game… this episode is the reset you didn't know you needed.  This… is A Bit of Optimism. + + + Join Don for a live Q&A on Leaderful on April 27th at 12pm ET: https://leaderful.simonsinek.com/browse/events/OMNjQIJ19cDDjjYRFbIge  Join the Leaderful app! Listeners can use promo code: STORY30 when you download the app or sign up at simonsinek.com. If you want more of Don, check out his Corporate Competitor Podcast: https://www.donyaeger.com/category/corporate-competitor-podcast  + + + Chapters 00:00:00 The Power of Appreciation: What You Look For, You Find 00:02:02 From Delivering Newspapers to Sports Illustrated: Don's Journey to Journalism 00:04:21 Don’s 12-Year Mentorship with Coach John Wooden 00:06:50 Coach Wooden's Philosophy: Pyramid of Success 00:09:00 The Bill Walton Haircut Story: How Wooden Managed Ego and Held Everyone to the Same Standards 00:10:33 Building Better Humans, Not Just Better Players 00:14:36 The Love Letters That Changed Don's Marriage 00:19:35 Looking for Things to Love: The Mindset That Changes Everything 00:22:23 Leading with Employee Care Over Customer-First Mentality 00:33:55 What True Mentorship Really Means: It's Not Transactional 00:47:07 Why Aren't More Leaders Following Coach Wooden's Example? 00:53:17 The Best Storytelling Advice: Know Your Audience + + + Simon is an unshakable optimist. He believes in a bright future and our ability to build it together. Described as “a visionary thinker with a rare intellect,” Simon has devoted his professional life to help advance a vision of the world that does not yet exist; a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are and end the day fulfilled by the work that they do. Simon is the author of multiple best-selling books including Start With Why, Leaders Eat Last, Together is Better, and The Infinite Game. + + + Website: http://simonsinek.com/ Live Online Classes: https://simonsinek.com/classes/ Podcast: http://apple.co/simonsinek Instagram: https://instagram.com/simonsinek/ Linkedin: https://linkedin.com/in/simonsinek/ Twitter: https://twitter.com/simonsinek Facebook: https://www.facebook.com/simonsinek + + + Photo/Video credits for this episode: https://tinyurl.com/ycxdw52s

Simon here, interrupting Simon. Before we start this episode, apparently there's this new thing called apps, and they're very popular right now. So I made one. Mom, I made an app. It's called Leaderful, and it's for leaders who choose to live the leadership lifestyle. It's chalk full of content to help anyone be the confident, connected leader they want to be. And we host live events. So if at the end of this episode, you have a question for Don, join. him live on April 27th at 12 p.m. Eastern for a live Q&A. Download the app or visit simonsenic.com and use the code story 30 when you become a member of leaderful. I'm constantly looking for things I appreciate, things I love. And if you're looking for things you love in your friendships, in your relationships, if you're looking for things you love, you see more of them. Oh, this is a great lesson. Your job becomes fine things I like. You make it your job to where people are actually going the extra mile, doing a little more, you know, doing good work. Even if it's a small thing, sort of say thank you, and you'll find you get more of it.

Don Yeager is the preeminent expert on John Wooden. John Wooden is the greatest coach in college basketball history. Whether you care about basketball or not, if you're interested in leadership like I am, you have to study John Wooden, which means you have to talk to Don Yeager. This is why I was so excited to have Don on the podcast, to talk to him about love letters. With the release of his newest book, Mastering the Art of Storytelling, Don has written 44 books, including 13 New York Times bestsellers. A former associate editor at Sports Illustrated, he's interviewed the great athletes of our generation,

Michael Jordan, Serena Williams, Michael Phelps, and, of course, Coach John Wooden. And it was Coach Wooden, who taught Don the power of a good, love letter. After Coach Wooden's wife passed away, he wrote her a love letter. She had passed away on the 21st day of the month. And every month for 25 years, on the 21st day, he wrote a love letter to his wife. When Dunn asked if there was anything in those letters, he wished he would have said while she was alive, wouldn't reply all of it. Coach Wooden taught Dunn something simple, but easy to forget. We assume there will always be time. but the best time to tell someone how much they mean to us is now.

This is a bit of optimism. Don, it's such a treat to sit down with you. Your ability to tell a story, quite frankly, is captivating. And I know you've written a million books and had bazillions of New York trans bestsellers, but to sit down with you is something completely different. I could just sit back and listen to you the whole time. In fact, why don't I do I sit back and let you just tell stories and I'll be very, very happy? You started as a journalist.

Yes. What did you do as a little kid? What did you want to be when you grew up kind of thing? How did you come to journalism? So it's funny, you could argue that I was meant for it. My father was a preacher. We lived in Hawaii, which is where I was born and raised. We ended up in Japan.

Military? No, he was a Methodist preacher. But we were in Japan. and my job was to deliver the newspaper, the stars and stripes. So I would get up every morning, 5 a.m., go to the place, pick up the papers, deliver them to every place. Then I would come home, and I would put recording session in progress on the outside of my door, and I would read parts of the newspaper into a recorder,

and then I would opine about what was happening at that time. And I'm 11, right? And so I loved the news. I loved what was happening in the world. I loved curiosity. And journalism really just kind of satiated all those things for me. So you were in the school newspaper in high school. I mean, one of the very few people on the planet that literally was on a path from a young age and actually brought that path to life.

That's correct. And you studied journalism. And then where did you go? You went to Hard News? It's in Allstate University. It's in Indiana, isn't it? In Indiana. I went to the San Antonio newspaper.

Antonio Light. It was the large paper in San Antonio. From there, after a couple of years, I went to Dallas Morning News. And then I wanted to do politics. So I moved to Florida to be the political editor of a large newspaper. After a few years of that, I got an opportunity to go to Sports Illustrated, which was quite the departure. They only have, you know, about 30 writers for Sports Illustrated at any given time. And I got an opportunity to be wrapped around these people that I thought were so fantastic at every given moment and learn every day about the great skill that it took to tell stories as they did. So what Sports Illustrated did is it opened up an opportunity for you to meet John Wooden. And you, I think it's fair to say, are the preeminent expert. Is that the

word to use on John Wooden? You spent more time than anybody else other than probably his family and maybe his teammates. John Wooden's great basketball coach. who's considered one of the greatest coaches of all time. His philosophies are sort of counter to what a lot of people think. One of the reasons I wanted to sit down with you, I wanted you to sort of share some of the things you learned from getting to spend so much time with Wooden about leadership and human behavior.

He would have been, by the way, he would have been a great Simon Sinek fan because you and he think so much alike. He believed that performance was fully driven by relationship. In fact, there were times he would run practices without basketballs, right? I mean, think about it. You're a basketball team practicing shooting,

but there's no ball in your hand. You had to visualize seeing it, going it through the net. Because the truth is, if you actually shoot it, there are times it won't go through the net. Right. So he actually understood the power of the mind

and how the mind could influence behavior. And for people who don't know who John Wooden was, can you just sort of very quickly say why he's renowned and famous as a coach? He won 10 national championships while being the head coach at UCLA. Is that a lot? That is twice as many as anybody else in history. And that statistics remains today.

Right. He won a double-in-out of the highest winning team. Mike Shoshchevsky has five, right? Adolf Ruppet, Kentucky has five. But those two are the next in line after John Wooden's 10, right? And so, and he did that in a 12-year window. Right. He won seven championships in a row at one day.

age. Wow. I mean, you're playing with different players all the time because kids graduate. So you can't simply, people can't brush it off and say, oh, you were lucky you had the best players for 10 straight years, right, or 12 years. Because that's impossible in college. Right. They're rotating off. They're moving. And back then, college players could only play for three years. So he had, they constantly be developing. And the thing that made him so special was that he didn't have a way of winning. He adapted to the players that he brought onto his team. So if he wins the national championship with a 6-5 center, that's awesome. But the next year he has Kareem Abdul-Jabbar, who's 7-1. And so, you know, now it's a whole different game for him. He changed based upon

the assets, the talent that he was graced with. The thing that I have found amazing about Wooden is the winning most coach in college basketball history was not obsessed with winning. No. And I think for a lot of leaders who are obsessed with performance and obsessed with outcome and steps with hitting numbers to learn that somebody who had greater success than all the others was not obsessed with winning reconcile that for me yeah when he was a high school basketball coach high school coach he built a pyramid of success right of here are the blocks of what it meant to be successful and its industriousness and its willingness to be team first it was all these elements and you get to the very top and the top block was greatness and he believed that you build

yourself toward greatness you don't take greatness on and he's he never in any of these conversations talked about what it meant to be a champion. What he talked about was what it meant to be great in our universe. If we're good together, good things will happen. So I understand it wasn't about being a champion, but being a great teammate. Correct. And being a team of great teammates. It's one thing to have. So many teams have good superstars and good teammates. And often the teammates are the people that are just lucky to be here. This was your best player also was committed to being a servant leader. How did he manage ego?

So let's take someone who truly is gifted in the sport and maybe even has a remarkable work ethic. And so they carry themselves like, I'm the champ, you couldn't win without me. How did he manage ego? How did he teach, you know, teamwork to somebody who truly is a superstar? Because he understood. Now, he used to say, I believe in patting everyone on the back, some of them a little lower than others, but I've had everybody on the back. But his whole model of leadership was this concept that you need to have a series of standards that you will hold everyone to, your best

player, your worst player, everyone abides by these standards. And sometimes your best players will push that envelope and try to see, do you really mean that for me? I'm the best player. He had Bill Walton, right? One of the greatest centers of all time. Bill Walton liked to have hair that was a little longer than everybody else it was the 70s when he was there and so one day it's for bill's senior year he was the two-time national player of the year senior year he shows up for the team photo with long hair coach wooden had a rule we don't have long hair here because he believed that you would shower after a game most people don't dry their hair well you go out into the cold winter of some of the places they played you catch a cold if you catch a cold you're not available if you're not available we don't

win, you're disappointing the rest of your team by not being available. So he had a rule about hair, but he had a reason for it. Right, right? And Bill Walt decided, you know what, I'm best player in the world, best player in America, I'm just going to show up with long hair for senior photo day. And John Wooden said, Bill, what's the story with your hair? And he says, well, coach, you always encourage me to think independently and independently, I think long hair is good. And he says, you know what, Bill, I'm so glad you think that way. and we'll miss you. And Bill Walton went out, found a kid who was riding by on a bicycle,

asked the kid if he could borrow the bike, rode the bike down to a haircut place, came back 30 minutes later with his haircut because he realized Coach Wooden had a standard and will miss you was his answer. And suddenly Bill Walton didn't want a test to find out is being the best player on the team going to give me a little more grace than anybody else?

So when you say standards, you don't mean performance standards. Oh, no. These are standards of being. This is what it means to be part of our team. This is how you're going to cheer for each other. He required that if you hit a basket but somebody had passed you the ball, that as you ran down the court, you need to look at him and point and say, thank you.

Thanks for passing me the ball, right? Because there was joy in recognition, right? And often the person's scoring gets all the recognition. The person who passes it doesn't. He required that on the way down the court you look for any point. It's an ego check too, right? Yeah. Like you didn't get that basket by yourself.

We do this together. Yeah, one of his players actually said to him, but coach, what if I go to run down the court and the guy's not looking at me when I want to point at him? Coach said, if the guy knows you're going to point, he'll look at you.

And so these are the kinds of things he was doing to try to establish not basketball standards, human standards. And if they were better together as a group of humans, they could win and they won a lot. And now name some of the players who came out of those teams that went on to the NBA.

Oh, my gosh. Well, at one stage, he had 26 All-Americans who played for him over the course of several years. Walton, Carleton, Crimin O'Dibar, Sydney Wicks, Henry Vivi, Marcus Johnson. I mean, you know, some of the biggest names in college and then ultimately the NBA all came from that window of time when they were best in class. And I mean, I'm not a huge basketball fan. I do know Krem of Bill Jabbar. Yeah. And one of the things I know about him is he was known for his humility and being a great teammate.

And even though he was a remarkable talent and a remarkable player unto himself, there was a, and to this day, a humility that he embodies. And so much of that came from the environment. You know, this is why I think it's important whether somebody likes, you know, I'm not a basketball fan, but I do love the stories about Wooden because they're so universally applicable. Correct. And, you know, even the stuff I talk about it's so funny in this modern day and age, you know, I'll talk about. about Navy SEALs and I talk about these high performing teams or wouldn't. And in all those cases, we're talking about high performing teams and people take those ideas and those lessons and they try to apply them to individuals. And I always get a kick out of that. Right. You know, we forget that

all of the stuff only works because there's a group of us. A company is literally a group of people. That's what a company means. Right. And if we can pull that group of people together, if they can believe that when they've given you an assist, you'll notice them, right? It's amazing how many you'll get. What kind of person was wooden? Sometimes what they're known for and who they are, sometimes align. You hope they align. You know, they always say don't meet your heroes. Yeah. And I will tell you over the course of my career, I've had some of those experiences where you don't want to meet your heroes. John Wooden does not apply. He was the greatest coach of all time and a better man. He taught me in our conversations, and I had the honor over 12 years, the last 12 years of his life

to have him as a mentor. And we ended up in a relationship that allowed me every, other month for 12 years to fly to California to spend a day with John Wooden. And the responsibility was mine to lead the conversation. I had to come with a series of things I wanted to learn. When I was out of questions, the session ended. He was no BS. Oh no. And every day had to open in a mentorship relationship with him. I had to say, coach, here's what you taught me two months ago when we were here together. Here's how I've used it in the interim and here's how I'm better as a result. He needed to hear that it wasn't just me soaking up time with him. He needed to know that he was changing me. Because otherwise it's his time wasted, right? Right. Exactly. It was my job

to come prepared, to let him know how I used what he taught me to be better. Better as a father, better as a husband, better as an employer, better as a, you know, a speaker or whatever it is that I was outdoing. He wanted me to come back to him with, was something I took and show how I became better as a result. How did he help you be better a husband? Coach Wooden, he's a great husband. He married the only woman he ever kissed. And sadly, she had passed away 25 years before he did, ultimately.

And in that 25-year window, she had passed away on the 21st day of the month. And every month, for 25 years, on the 21st day, if you were there to meet John Wooden, if you had an appointment with Coach Wooden, he didn't meet with you in person until he wrote a love letter to his wife. And he wrote these beautiful love letters. His penmanship was fantastic. And they would often be a page,

maybe a page and a half long. And then he would seal the envelope, lick it, seal the envelope, and he would walk into her side of the bedroom where her bed was still made up, where she would have slept, and he would take last month's letter and put it in a box,

and he would take this month's letter and lay it on the pillow. And, you know, one year, and I could probably tell you exactly when it was. It was November-ish of that year. I happened to be there on the 21st day. And so I had to sit at the dining room table as coach sat there at the table and wrote this letter to his wife. And when he came back after putting it at her bed, he looked at me and I said, coach is, You write these letters every month. You've been doing it for years.

They're boxes of them. Is there anything there you wish you had said to her while she was alive? And he said, all of it. I said, excuse me? He goes, oh, yeah. He said it's one of the great weaknesses for most of us as people, our friends and our love ones, the people that we are so engaged with. We're so busy telling everybody else how great they are.

We forget to tell them how much we love them. And he said, I wished I had said these things when she was alive. He said more to his players than to his wife. Yeah. Yeah. And he said, so these letters are my opportunity to get that, get that chance. Well, I was so taken by it that that year I went home. And for Christmas, I gave my wife a box with 52 letters in it. 52 letters where I expressed to her something I loved about her in each and every one of them.

I made a list and I knew what I wanted to write in each letter. And that Christmas, I mean, like, it didn't matter what I gave her, that was the gift, right? And it meant so much to her that the next Christmas, I did it again. And I did it again. And just last Friday, she opened letter number 848. So however many years that is, is how many years it's been since I started doing it. And they're all different. So she takes the box and opens one a week.

She opens one a week. And then she keeps all the letters. She loves to point them out to my daughter and say, by the way, I hope, one day you marry somebody that will love you enough to write you a letter. Wow. And, yeah, Coach Wood made me a better husband. I mean, there have been times when in our relationship where I'm pretty sure the letter saved me, you know, because I may have done something that really made her mad and whatever

it might be. And then ultimately she'd go, yeah, but this guy's written me 500 letters, right? You know? And so, I mean, there's a little grace that I get, a little extra grace that probably plays into our marriage. It's been without question. It's John Wood to change my life.