Leadership And Life Lessons Learned From Coaching

I recently had one of those great “teacher moments” a few days before Christmas break.  I received a text from a Basketball Coach, who is also  a Teacher. The text showed a clip from his basketball game that night.  It turned out to be the winning play that the coach had drawn up after calling a timeout.   

The text under the video clip said “Coach, I drew this up after calling a timeout and it kept our undefeated streak alive! I thought I would share and knew you would be proud.”  

This came from a player I had last coached in 1998 and had last seen at his mother’s funeral in the mid 2000’s. We had managed to stay in touch through the magic of social media and exchanged a few random texts over the years.  We keep promising each other that we will get together eventually–we may or may not– but the fact that after a big win he thought to share his success with me still gives me goosebumps.  You see, you develop a bond with players, with teammates, that  is really second to none and lasts a lifetime.  

My views on competition and athletics have evolved over the years.  My disgust with the pressure that some parents put on their children playing sports and their unrealistic expectation that their child will get a scholarship has left a bad taste in my mouth.  Yet, when I reflect on my time coaching varsity basketball I always smile. I smile because I have great memories and it taught me so many lessons about leadership and life.

The championships were great,  the lessons learned invaluable, the funny stories worth treasuring, but nothing was more important than the relationships developed. What I value most about that time is the connections I made with my student-athletes.  When I refer to these “kids” I always refer to them as “my players.”  

“Hey Rebecca, Did you see the text I got from my player, Mariah?”

“I ran into one of my players today and you won’t believe it, Mike is coaching now.”  

“Who did you go to the Knicks game with last night?”  “A couple of my players.”  

It doesn’t matter that they are now grown men, that we may not have seen each other in 15 years, I always refer to them as my players and they always refer to me as coach.  They know I will be there for them and I know them for me.

One of the many things I miss about coaching is being affectionately referred to as Coach.  I still turn my head when someone calls out Coach and I am still shocked when I find out they weren’t talking to me.  Not sure  I will ever get used to being called Doctor, but Coach was an easy moniker to adapt to and a hard one to give up.  

The bond you develop spending hours together, months out of a year trying to accomplish the same goal, is a bond that is not easily broken.  I am proud of all of my players.  Some are coaches, some are teachers, some administrators, one is a grammy winning music producer, one works for ESPN,  one is even an extreme right wing political writer whose political  views are a bit out there, but I am proud nonetheless. He is becoming the 2018 version of Rush Limbaugh, but this version has red hair and is still chiseled, full of muscle like he was when we won league MVP in High School. I may not be proud of his politics, but I am proud of his passion, dedication, and desire.  These were characteristics and life lessons that we learned together on the hardwood in Boiceville, NY.

I have had players who have hit rough patches too.  One of my favorites was recently released from prison after a 10 year stint.  We caught up for a few lunches and, after speaking to him, I am just as proud of him as any of “my players.” Despite mistakes he made, horrors he faced, and challenges he still has ahead of him, he never makes excuses, never lays blames, has never let the flame flicker out of his eye.  He has dusted himself off, chosen to accept responsibility and to move on with, and to enjoy, his life. I have little doubt he will find success, peace, and happiness.  Am I proud of him?  You bet!

Another one of my players lost both legs in a horrific car accident.  This player didn’t actually suit up for one of my teams, but he was around the team so much that I still see him as one of mine.  How did he react to losing his legs, to seeing them sprawled across on Route 17 as he lay on the cold ground waiting to die?  He picked himself up, figured out his new normal, and decided to enjoy life rather than worry about what could have been.  Today, I see him talking sports on his live Facebook channel or yucking it up with celebrities on broadway, athletic events, and movie premiers.  He is one of the most positive people I know. He remains passionate about a sport he can no longer play, he enjoys life to the fullest and in the words of Carly Simon he is “where he should be all the time.”  

I like to think I have helped my players to be better people, make better decisions, and taught them what they needed to know, but the truth is they have and continue to teach me more than I have or could ever teach them.   

As my career has progressed what I learned from coaching about relationships has just been reinforced. If you want to motivate students, if you want to motivate teachers, if you want the best schools, if you want to optimize learning, and if you want to be just plain happier–it all starts with people and it’s all about relationships.  

My relationship with my Father was at its best when I coached.  He taught me a lot about coaching and a lot about life, but it wasn’t all sunshine and lollipops because with Frank nothing is.  He had an obsession with being “preeeepared”, which he would often say over and over again in his deep Italian, all-knowing growl.  

I remember one scouting trip that was a bit over the top.  We had to travel over an hour to see a dreadful team that we ended up beating by over 30 points.  This was towards the end of my coaching career.  I was already serving as a Principal and Athletic Director, I was newly married and had arrived at work at 7:00 AM, worked all day, and then ran practice until 6:00 when he showed up at the gym insisting we went scouting.  

God forbid we weren’t “preeparrred.”   

We went to the game, brought our video camera, and strategically placed ourselves directly across from the opposing coach.   Frank made sure to make plenty of grunts and groans as he lumbered his large frame up the bleachers.  He insisted on making a scene because it “pissed the hell” out of the other coaches.  It didn’t matter how embarrassed I was,  Frank was going to do what Frank was going to do.

Finally, the game was over and I was ready to return to my new wife.  It was after nine, and I had to get up and do it all over again tomorrow so you can imagine why I said no, when he wanted to stop for dinner.  

I received a slight curl of the lip with a look of death in his eye and despite my best efforts, I recoiled a bit, remembering the backhands that I used to receive as a kid that often bloodied my lip.  After traveling another 15 minutes, he started with his usual plea to fill his belly.  

“Kris, I’m thirsty, are you?’’  

“No Dad, I just want to go home”

To which he replied, “Well, I need a soda” and started to pull into a local pizza shop.  

He tried to get me to go in with him, but I refused. He ate his meal while I stewed in the car.  It didn’t matter how hungry I was, there was no way I was going to give him the satisfaction of having a slice.  I know I was being a bit spiteful and childish and like to think I would react differently today.  After 20 minutes or so he came out with a grin on his face, sauce on his chin, and his large belly full.  

I couldn’t help seeing the steam coming off the piping hot slice of deliciousness.  He handed me a slice as he got into the car and I shot him the death glare back and said I didn’t want it.  He shrugged as my anger continue to grow, but then it hit me! I knew how I would invoke my revenge.   We continued the ride home in silence, the only thing filling the car and our noses was the amazing smell of sauce, cheese, and bread!  I could barely refrain from taking a bite, but I knew I couldn’t because it would ruin my plan.

Finally we arrived back to the school where my car was parked. At that point Frank, always predictable when it comes to food, said exactly what I knew he would.  “If you aren’t going to have that slice, give it me. I don’t want to see it go to waste”


“Sure,” I said with a sly grin and I reached down for the slice and handed it to him.  It took Frank a second to realize what happen as he raised the slice to his watering mouth.  

That’s when he saw it, the large perfectly formed indent of my size 11 boot.  I had stepped on the hot pizza so carefully that you could see the perfectly formed Timberland logo.  

At first, he looked like he was going to cry, but that cry quickly turned to rage.  Luckily, I had made it to my car before the metamorphosis occurred.  I looked back at Frank, just in time to see the slice fly through the air and land with a splat on my windshield. Frank was barking expletives that can not be repeated here with rage that you wouldn’t understand unless you have seen Frank lose it.

I learned a few things that night, but probably the most important was revenge feels good at first, but afterwards you are still hungry.

It is a challenge not to be vindictive as a leader.  It is challenge not to want our pound of flesh, but the best leaders do not take things personally, they accept what they cannot control, embrace and cultivate strengths, and demonstrate empathy for others’ weaknesses.  I have learned over the years that the best leaders forgive. You see, forgiveness takes greater strength than vengeance.  

I still remember that first year of coaching like it was yesterday. The courage I had to build to bark orders at a bunch of 16 and 17 year olds when I was a mere 22 myself.  The looks of pity and sarcasm as I led my team on the court to coach against actual men.  I also remember breaking my foot by kicking the bench.   I thought that was how you were supposed to act: to yell to scream at the refs, to agonize over every play,  yell after every miss.  

It was only after I learned how to actually coach that I realized how counterproductive this was.  

I yelled and screamed because I didn’t know any better or how to actually coach.   

As I became a better coach I learned to remain calm during a pressure packed moment, pick my spots with refs, yell at kids for selfish play or lack of hustle, but never, ever for a missed shot.  

That didn’t mean that I wasn’t a passionate coach. I was; I kicked my leg with every foul shot, bounced up and down the sideline in an effort to motivate my players, the fans, or because I was just so into the damn game!  

Yet, I learned that it is often better to think, to remain calm, to be the voice of reason.  These are characteristics that have helped me as a leader.  When I see a teacher screaming at kids I now understand they do not know better, so I try to help them.  I now know that during a crisis (they happen more they you would think) the leader needs to remain calm, to be the voice of reason, to let the school know it’s ok and that someone is in charge. My time on the court helped me understand this lesson much quicker then I would have learned otherwise.  

As leader it is important to remain humble, to give credit, not take it, and never throw your success in the face of others.  I learned this the hard way one night in a tiny gym in upstate New York.

We were playing the four time defending league champions, a team that had two future division one players on the squad, a team whose coach enjoyed blowing teams out, often by 40 or 50 points.  We were playing in their tiny gym, with their maniac fans screaming.  They hadn’t lost a league game in over three years.   

The fact that we were still in the game going into the 4th quarter and only ended up losing by 11 points was a small victory.  I knew my young squad had promise and had a good chance to meet them again in the league championship game.  

I was excited, really the only time in my coaching career that a loss seemed like a small victory.  That’s when the reporter approached me.  He seemed just as excited and shocked as I was that a team lost by less than 30 to the mighty Red Hook team.   When he asked me how I felt about the game and our opponent, that’s when it came out of my mouth…I felt like Ralphie when he changes the tire in A Christmas Story.  I knew as soon as it started to come out of my mouth that it was a mistake, but I couldn’t stop myself.  

“ I am very proud of how my boys played tonight, I think we were able to dispel some of the Red Hook mystique!”

What the? Did I actually say that?  Would he even print it? Was it as bad as I thought?  

He did and it was.

Flash forward several weeks…We had done it; the upstart Indians made it to the finals.  We would be playing at the local community college.  The game was sold out– 2,000 plus in attendance, people sneaking in to see the underdogs led by this 23 old Marlboro grad vs. the league’s most successful coach, a veteran who also graduated from Marlboro and happened to have been friend of my parents. He had taught me how to swim, our families had been on vacation together; he and my Father spent many nights on the phone talking sports and life.  This was the type of story that High School Sports fans love.  

Everyone I knew was at the game and we were ready.  That was until the opening jump ball.  They proceeded to put an [email protected]# whipping on us like no other.  The coach never removed his starters or took off the press; the only positive from the night was we kept them under 100 points.  When what seemed like days of torture and embarrassment was over I looked up at the scoreboard and saw it 98-38.  Yikes! I left what was supposed to be my coming out party in shame.  

Would we have won if I had not made those comments?  Probably not, but my stupidity sure didn’t help.  This was confirmed when the paper came out with the all star team. Several Red Hook players obviously made the team.  When asked about their least favorite part of the season in the standard question template, all of the Red Hook players said the same thing “When people think the Red Hook mystique is gone”  How about the question about their favorite part of the season?  You guessed it “proving to everyone that the Red Hook mystique is still intact.”   

Did I learn from that?  I sure did; I learned to be careful what you say to the press, but also never boast about your successes or perceived success. And, sometimes it’s  just better to keep your big mouth shut!

Over the years I have learned how important it is for leaders and people for that matter to demonstrate perseverance.  It is easy to be positive, happy, productive when things are going well.  The true test of character is how you cope when life doesn’t go according to plan.  

You didn’t get the promotion you want?  Do you pout or hold your head high and look for ways to improve so you get it next time?  

You great idea doesn’t work according to plan, do you blame others or look for reasons why?  

Your boss is unhappy with your performance?  

You get the idea; it’s during the hardest times, the biggest disappointments when we show who we truly are and we also have the opportunity for the greatest growth.   

Coaching basketball was instrumental in me learning this very important life lesson.  After our big loss in championship game, we were all a bit down. We knew we had a strong core returning but we were losing three starters including our leading scorer and moral compass, Cory.

Cory, more than any person I have ever known, demonstrated perseverance. Cory had lost his sister the year before I arrived to the school due to a undetected heart defect.  She passed tragically while the family was on vacation. If that wasn’t enough, his Mother passed after a long, courageous battle with cancer during his junior year. Despite all of this heartache and tragedy, I never once heard Cory complain, give up, or stop believing that as a team we could accomplish anything.  I pushed Cory harder than any player, had the highest expectations for him, and never once did he fail to rise to the occasion.  

I was most upset for Cory after the big loss because I knew he wouldn’t get another shot, yet Cory had one more sacrifice to offer the program.   He asked if I could open the gym and the team could get together for one last time. Cory then gave one of the best and most selfless speeches I have ever heard a player–or coach for that matter–give.  

He talked about how much we had accomplished as a team, how important it was for us to build upon this success, and, most importantly, if we stuck together, worked hard, and did all of the little things right we would be able to accomplish even more.  

I often think back on that speech when I want to motivate, but I never seem to do it as well as he did that day.  I know if Jon Gordon was present he would be able to write another amazing motivational book based on Cory’s words.  I learned a lot form Cory that day. I learned that sometimes the greatest lessons are taught to us by kids, and that when the going gets tough it is the true champions who rise and persevere.

I once studied coaching as much as I study education and leadership now.  John Wooden was my go to.  He was the most successful college coach of all time and he did it the right way: with class, dignity, and integrity.  He was the model I tried to strive for, but, honestly, always fell short.  

One thing that did resonate with me was how he talked about the process.  He didn’t measure success by wins and losses, but rather on doing things the right way day in and day out.  That’s exactly what our team set out to do each and everyday in practice and games.  We stopped worrying about the score and started worrying about doing it right.  The results were amazing!

We ended the regular season ranked in the state, division champs, and once again finding ourselves facing Red Hook in the league championship game. The “following the process” helped us get to this point.  That and the fact that we had a point guard who rarely missed 3 pointers, a 6’5 dunking machine for a center,  and a uber athletic swingman who had a motor that was only matched by his desire to win.

The day before the game we talked about playing hard, doing things the right way and putting team first.  When I read Jon Gordon’s The Hard Hat it brought me back to that time and that team.  I find Jon Gordon’s books so motivational while at the same time being so very practical. I never thought the time would come, but Jon Gordon has replaced John Wooden as my go to for coaching motivation.  

The game finally arrived, the scene similar and very few in the gym gave us a shot to break Red Hook’s 68 league winning streak.  We did, and it still goes down of one of my proudest moments.  I can still see the joy on my players faces as they poured the water jug over my head, much to the shagrin of league officials. I can still see my Father deftly charging the court looking for someone to hug Jimmy V style.  He didn’t let his large frame or the water boy that he nearly killed slow him down.  I can still see the tears of relief in my mother’s eyes knowing that the pain of the previous year’s debacle would be avoided.  

What I remember most though is Cory pumping his fist, eyes a glow with joy.  He showed only happiness and no regret that it wasn’t him in uniform that night.  He may not have played a minute that night, but we could never have won the championship without him.  I often see him as the backbone of our program. Our success that night and in the future could not have happened without him.  

I have tried to remember over the years not to let the “score” get in the way of the process.  In our schools, grades and test scores often get in the way and hinder true learning.  If we can get to the process of learning and stop worrying about the grades and test scores, our schools will be so much better off.  

Yeah, I miss coaching, I miss being called coach, but I would never give up the memories and the lessons learned.  When I think about the best educational leaders, I realize they are, in fact, coaches who happen to be coaching a different and more important game.