What I Learned About Leadership From The Last Dance

How one of the greatest sports documentaries of all time forced me to confront what’s required to be a great leader.

Allow me to (re) introduce myself my name is Geoff.

I live in Brooklyn, but i’m from the Bay Area

I’m a Strategy Director at an esteemed advertising agency in New York.

And I have an unhealthy obsession with sports and hip-hop culture.

It’s been a while since I’ve written anything for myself. So for my first foray back into writing I wanted to take something that I love and know very well (basketball) and apply it to something that i’m actively trying to learn more about (leadership.)

If you’re like me or over 50M people across the United States, you’ve probably seen The Last Dance by now. Outside of it being one of the greatest sports documentaries of all time, I found that some of the subjects explored in the doc had some interesting parallels to the worlds of business and leadership.

We discussed some of this during a podcast I’m on called Marketing Misfits, but I was so intrigued by the conversation I wanted to investigate the topic further.

So in this article, I’ll cover lessons I learned from The Last Dance, and give my own personal take on how these lessons can help make us all better and more effective leaders.

I know you’re asking yourself, if I literally just said I’m learning more about leadership, then why the hell am I qualified to write on this topic?

I don’t have a great answer for that. But it just felt like a perfect storm of information was hitting my brain around the same time the Last Dance was taking place in my living room.

  1. While the Last Dance was on-air, I was in the middle of reading a book about how my favorite sports dynasty fell apart. Some of the lessons you’ll read in this article, but if you want to go deeper into the topic you should read this book.

With that being said, let’s get into some of the leadership lessons from The Last Dance and learn us somethin’ right quick.

Lesson 1: Tough Love Don’t Work For Everyone

Mike’s “tough love” leadership style was well documented in The Last Dance. He was in many ways considered a tyrant to his teammates, often berating them, chastising them, (or even sometimes punching them in the face.) But no matter what you think of the approach, you can’t argue with the results. Mike won championship after championship, winning two threepeats, and collecting six rings in the process.

This “tough love” approach is not only unique to Michael, but it’s an approach that has been celebrated in the world of sports and has become ingrained in the culture of business. Leaders delivering harsh criticism (without providing guidance) has been masked as “putting a fire underneath people” or inspiring people to elevate their game to a “championship level.”

Although this approach may work for some people who need an extra push to reach their full potential, it frankly does not work for everyone.

This is because people are people. People are unique. People have different lived experiences. People have different motivations. People have different things that inspire them. If I were to break this down through the context of sports I would say there are three types of athletes. (Maybe there are three types of employees too but I haven’t thought about it that deeply yet.)

  1. The Gifted. These are the people who were born with athletic gifts and playing a professional sport at some level is part of their manifest destiny. Because they have gotten by for so long with their natural talent, many times they can become complacent and still achieve some level of success. These are the type of athletes who could probably use a little tough love or an additional push to take it to the next level. Example: Ben Simmons

When leading a team it’s not just about you, you have to start with your personnel. What motivates them? What are they good at? What do they struggle with? What gets them going? Are they complacent and need a little push? Or are they on edge and need to know it’s ok to take the chip off of their shoulder?

Taking all of these factors into account will make you more of an effective leader. Because this isn’t about looking at yourself and using a leadership style that motivates you, it’s about understanding your staff to uncover the things that get them going.

Lesson 2: Dealing with Talented Assholes

Michael Jordan may be the most gifted athlete we’ve ever seen grace this planet, but he was also extremely difficult to work with. In the world of business Jordan would likely be referred to as a “toxic worker” — someone who’s immensely talented and brilliant at what they do, yet their mean spirited nature and overall attitude create a horrible workplace culture.

In today’s world it’s easy to say that there’s no room for a toxic workplace culture. But what makes this matter complicated is when the “toxic worker” is instrumental to an organization’s success. After Jordan departed in 1994 the Bulls won 2 less games than they did the previous season, but they fell short of a championship. Steve Jobs was notoriously difficult to work with, but Apple hasn’t seen nearly the same level of innovation since his death.

So this brings up a great question. What’s more important? Hiring talented assholes who make the company successful (even if they drive everyone crazy) or maintaining a positive workplace culture (even if you never win anything.)

The answer depends on what your ultimate goal for your organization is.

Short term success or long term value?

Or to put it in sports terminology …are you chasing rings or building a dynasty?

If you’re chasing rings. You can sign a bunch of talented players with difficult personalities to 1–2 year deals. You can make a run at a championship and if you win, the investment and the drama was well worth it. If you lose, no harm no foul the contracts are over and done with. Any damage to the organization can be dealt with during the rebuild years. In a world of freelance workers and contractors some organizations might decide these type of deals are worth it to win a couple rings.

If you’re building a dynasty. The culture of your organization is always what’s most important. You’re trying to build something to last, and that means creating a culture that is bigger than one person.

One of the great things about sports is when people buy into something that is bigger than themselves. And although the Bulls found ways to win despite having a “toxic worker” on their team, they were able to become a dynasty because that same “toxic worker” decided to buy into something bigger than himself.

Lesson 3: You Can’t Win Without The “Buy In”

One of the main lessons we should take away from The Last Dance is how difficult it is to sustain greatness. The Bulls won 6 championships but were mentally and physically exhausted on the other side of both of their three-peats.

There are many factors necessary to sustain greatness, but more often than not, winning time and time again requires people to buy into something bigger than themselves.

Historically, some of the winningest coaches have not only set a clear vision, but they found a way to get their whole organization to buy into what they were selling.

Here are a few examples of this done well:

Phil Jackson and “The Triangle”: Lost in the story of Mike’s greatness is how instrumental Phil Jackson was to the Bulls success. There’s a reason that Phil has won 11 rings. During the doc we see how Phil had to get Mike to buy into Tex Winter’s Triangle offense. It was an unconventional offensive scheme and required Mike to pass the ball a bit more than he frankly wanted to. It wasn’t easy, but Mike eventually heard Phil out. He adjusted his game, bought into the triangle and started to understand Phil’s point about the value in trusting his teammates. The combination of the triangle offense and Phil’s zen/buddhist approach was unconventional at the time, but once the greatest basketball player to ever walk planet earth bought in, the Bulls became unstoppable.

Bill Belichick and “Do Your Job”: I’ll save my personal opinions on Belichick, but there’s no denying that he’s one of the greatest coaches of all time. His philosophy of “Do Your Job” was a simple philosophy based on the interdependency that is at the heart of a football team. If everyone does their job we’ll win the game. If the lineman blocks, the running back runs, the quarterback throws, the receiver catches, success is imminent. As long as everyone commits to executing their specific role then the team will be successful. Tom Brady bought into this concept so much that he took pay cuts throughout his entire career to ensure the Patriots remained a well rounded organization. Because if the success of the team is based on everyone doing their job, then you want to make sure you always have the best personnel to do the task at hand.

Now for an example of this not done so well:

Steve Kerr and “Playing With Joy”: (Yes, I am a Warriors fan. Yes, this is incredibly hard for me to type. No, I won’t be ok after this.) Looking back at the most recent dynasty of the Golden State Warriors, their run was one for the record books. 5 straight trips to the NBA finals, three championships, and a 73 win season. When Steve Kerr took over the team in 2014 the first thing he wanted to do was develop his own leadership style and coaching philosophy. Having come from the Phil and Popovich school of coaching, he understood how important it was going to be for him to develop a coaching style that was unique to his own personality and values. After visiting Pete Carroll at USC, Kerr decided that he wanted to lead with the concept of playing with “joy.” Creating a free flowing system that combined four core values of joy, mindfulness, compassion, and competition. Kerr created a system where players competed and gave it their all but also never took themselves too seriously. A strong sense of humor was encouraged, and loud hip-hop music was a staple of the Warriors team practices. In its simplest terms, the Warriors were winning and having fun doing it. This was most evident during the 2014–2015 run, but it changed once Kevin Durant came to town. Did the Warriors win back to back championships with KD? Yes. But they looked miserable doing it. The Warriors had lost their joy and lost their way. That was extremely evident during this infamous interview after a 128–95 loss to the Celtics. Kerr said the Warriors had to play with more “anger” and KD sarcastically responded that he thought the Warriors were supposed to play with more “joy.” The Warriors had walked away from the philosophy that made them successful, while arguably the best player on the team made it clear that he never bought into the philosophy in the first place.

The death of the Warriors dynasty should be a warning to any company looking to sustain long term success. If everyone doesn’t buy into the system, then the system will eventually die.

In Summary

There are many lessons we can learn from this doc, but one main takeaway we can all agree on is that there is not a one size fits all approach to leadership. At the end of the day people are people. All with different motivations, triggers, things that get them going, and things that hold them back.

As a leader it is our job to give people the space to become who they were meant to be, but that’s not done by forcing our own agendas down their throats. It is accomplished by being clear with our expectations, by being adaptable with our approach, by better understanding the people we’ve been tasked to lead, and by using our personal values to create a system that everyone wants to buy into for the greater good.



Strategist. Thought Leader. DJ. Public Speaker. Increasingly curious about the world, in constant pursuit of the truth.

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Geoff McHenry

Strategist. Thought Leader. DJ. Public Speaker. Increasingly curious about the world, in constant pursuit of the truth.