10 lessons on leadership and Success from Michael Jordan’s ‘Last Dance’

His unique brand of greatness goes far beyond basketball

Sherif Shafi
The Startup
11 min readMay 20, 2020

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credit: michaeljordanart

Lincoln, Mandela, Churchill, Thatcher, Jobs, or Gates tend to be the names we gravitate to when thinking of the purest expression of a Leader. They are so universally renowned that a first name is hardly necessary. But we seldom include iconic sports figures in their company.

Then comes an undeniable force of nature named Michael Jordan, and he forces us to reevaluate our traditional definition of the quintessential leader.

Sure ‘The Last Dance’ is a sports documentary. But once you look past the title theme, you find it shining a light on all the essential qualities we strive for in our personal and professional lives. It’s a story about insatiable ambition, steely determination, boundless belief, unwavering commitment, tactical excellence, and inspiring leadership.

MJ is widely considered the best basketball player of all time, and one of history’s most elite athletes. He singularly transformed the Chicago Bulls, leading them to 6 NBA Champions in eight years. Individually, he won the title of “Most Valuable Player” 5 times. In 2009, he was inducted into the Basketball Hall of Fame, and in 2016, he was awarded the Medal of Freedom by President Barack Obama.

Leader profiles tend to focus on their decision-making skills, charisma, ability to manage with a fist of steel and bend events to their will. But perhaps the emphasis should be on how they galvanized and inspired the team that led them to greatness. It’s true in sports, as it’s true in organizations. What’s a world-class maestro without the masterful orchestra behind them?

Over 14 years, Jordan transformed The Bulls into one of sport’s most dominant dynasties of all time. And by the time the transformation was complete, when Michael Jordan stepped back and looked at The Bulls, he saw his reflection in them. The drive, the ruthlessness, the decisiveness, and the insatiable competitiveness led them to many records still unbroken.

What’s instructive about ‘The Last Dance’ is the artful way it showcases the full arc of a leader’s journey, from the lone warrior who believes he can single-handedly take on the world, to an older, wiser leader, relying more on mental toughness than pure athleticism, trusting his teammates, and championing the team spirit.

Throughout ten riveting episodes, some of Jordan’s most distinct qualities shined through. While they were first perceived as individual skills, the further we sailed into the series, the more these skills washed over each player on the Bull’s team. It’s the contagious effect a unique leader like Jordan could have on a team.

1. DETERMINATION

Jordan played some of his most memorable games under impossibly painful conditions. He played through a violet flu; he played through food poisoning, and he battled past defenders who blatantly tried to injure him. He played through the heartache of his dad’s tragic murder.

But somehow, he always dug deeper within him to find that extra gear to get him and his team to the finish line.

“I’ve missed more than 9000 shots in my career. I’ve lost almost 300 games. 26 times, I’ve been trusted to take the game-winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.” — Michael Jordan, Last Dance

The ultimate crowning moment came in game 6 of the 1998 finals when he had nothing left in the tank, and missing his pillar, Scottie Pippen, with 40 seconds left. What followed, as Bob Costa aptly put it, “was one of the best sequences in sports history “ with Jordan first scoring, then running back to steal the ball from Karl Malone, and leading his team back down the court to deliver one last dagger shot to win the game and the sixth championship.

Takeaway: There will be many moments in our lives and careers where it feels like infinite odds are stacked against us. Layoffs, feeling stuck professionally, losing a huge pitch. It’s those moments that force us to tap into our hidden reserves of resilience and determination.

2. EMOTIONAL INTELLIGENCE

Emotional intelligence is largely an elusive and intangible thing. It’s defined as the ability to understand and manage your emotions, as well as recognize and influence the emotions of those around you. According to the Harvard Business Journal, Emotional intelligence accounts for nearly 90% of what sets high performers apart.

At the core of Emotional intelligence is Self-awareness, which is the ability to be aware of your situational surroundings and emotions in real-time. It leads to social-awareness, which is your ability to pick up on people’s emotions and act accordingly to get the best results.

To bring out the best in others, you must first bring out the best in you. And that’s where Emotional Intelligence becomes an essential ingredient.

For Jordan, it was a long journey to acute self-awareness and a higher level of emotional intelligence. The turning point was the moment he punched Steve Kerr in practice during the 1996 season. It seems like a moment that was long in the making, given his harsh treatment of teammates on and off practice court.

It clearly shook Jordan, according to Phil Jackson’s book “Eleven Rings: The Soul Of Success.” He started working with a sports psychologist who taught him to meet people where they are at their skill and motivation level, rather than expecting them to meet him at where he is.

He started trusting his teammates more at crucial moments, and he was rewarded many times thanks to unsung heroes like John Paxson, Tony Kukoc, and no none other than the recipient of the punch, Steve Kerr, who scored the championship-winning shot in 1997.

Takeaway: Leadership is about so much more than your business and technical skills. Those who excel in life are born with intangible qualities ingrained in them at an early age. Empathy, self-awareness, compassion are increasingly becoming essential attributes in an optimum performer, whether it’s on the court or in the boardroom.

3. DECISIVENESS

Michael Jordan will go down as one of the most ruthless and devastating split-second shooters in NBA history. Over his career, his winning shots decided dozens of crucial games, including two NBA Finals! He demanded the ball when stakes were high, his instincts impeccably guided where the ball should go, and he delivered. It’s what leaders do.

His assassin instincts helped define him and shape the Bull’s destiny, starting at the age of 19 when he scored the game-winner with 17 seconds left, winning UNC the NCAA championship, to 1989 playoffs sinking another last-second shot to beat a far superior Cleveland Cavaliers, to his ‘last shot’ in 1998 finals beating Utah for the Bull’s sixth championship.

“Once I made a decision, I never thought about it again.”
Michael Jordan

Another remarkably decisive moment is deciding to retire at the height of his career to play baseball. MJ was only 31 and just coming off winning three consecutive NBA championships. He had everything to lose but had the courage and decisiveness to go through with it regardless of the consequences.

Takeaway: Over one’s life and career, there will come those critical moments requiring swift decisions that could sink us or propel us to new heights. Decisiveness takes heart, courage, instinct, and belief to move us forward in an upward direction.

4. ACCOUNTABILITY

Accountability is a direct bi-product of decisiveness. Those bold decisions have consequences to you and those who follow your lead.

While MJ holds a record for most crucial game-winning shots, he also had his share of heartbreaking misses that cost his team dearly. Like every great leader, he took full accountability and came back the next game more determined to lead the team to victory.

There have been critical games where he was missing key teammates like Scottie pippen, and Dennis Rodman. It was never an excuse to lose a game or give his team a pass. He demanded accountability of himself and those around him.

Takeaway: The buck always stops with the leader, and you live and die with the team you have, not the team you want.

5. TAKE THE LONG WAY

There are beauty and wisdom in taking the long way. It teaches you patience, dedication, focus, and, most of all, expansive knowledge about the passion you’re looking to master. All of which are essential ingredients to success and steady leadership.

“Be true to the game, because the game will be true to you. If you try to shortcut the game, then the game will shortcut you. If you put forth the effort, good things will be bestowed upon you. That’s truly about the game, and in some ways that’s about life too” — Michael Jordan

MJ arrived inthe NBA in 1984 as a star, given all his heroics playing at UNC. He could’ve felt entitled to the fast-track to bigger fame and instant championships. But given the gift of emotional Intelligence and humility, he knew that UNC was then, and Bulls is now “Whatever people said about me, I still had to earn my stripes.”

There are no short cuts to earning your stripes. It only comes by way of a long journey going through high climbs, dizzying descents, many stumbles, and priceless lessons. And yes, you will arrive with more battle scars than you care to see, but every scar taught you a lesson and made you stronger.

It took MJ seven years to win his first championship with The Bulls. It was the long journey that prepared him to finally get past the Detroit Pistons and move on to beat the Lakers for his first championship in 1991.

“ He knew how to steer momentum; he knew how to get guys going, and not only was he that good on the offensive end, he was just as good as the defensive end” — Chicago Bull’s B.J. Armstrong.

Despite being an offensive force, and one of the all-time top scorers in NBA history, Jordan was also one of the best defensive players in the league. This is a rare quality for a top sniper to have such a well-rounded game on both ends of the court. This only comes with time, patience, and numerous hours of practice. It’s taking the long way.

Takeaway: There are no short cuts to success. But neither do you want it. You should relish and enjoy the long way there — the lessons, the late hours, the losses, the blood, the sweat, and the tears. Makes it all that much sweeter

6. POPULARITY IS NEVER THE GOAL, BUT THE LEGACY

It’s no secret Jordan was not the most popular player on the team. In various episodes of The Last Dance, he was called everything from bully to tyrant. But all those who were on record criticizing his leadership, also admitted to coming around years later and understanding the bigger meaning and purpose of his hard-driving nature.

“Winning has a price, and leadership has a price. So I pulled people on when they didn’t want to be pulled. I challenged people when they didn’t want to be challenged. And I earned that right because my teammates came after me. They didn’t endure all the things that I endured” — Michael Jordan, The Last Dance

One thing is for sure, Michael led by example. He was the first one at the gym and last one out. He shot on the practice more than anyone else. He played every game like it’s his last. “You ask all my teammates, one thing about Michael Jordan was he never asked me to do something he wouldn’t do.”

Takeaway: Tough love is hardly ever an instant hit with family or team members. But it has a way of aging over time like fine wine. Many of history’s most consequential decisions were deeply unpopular at the time, yet celebrated decades later.

7. FIND YOUR TRIGGER

If you plan on insulting Michael Jordan’s game, be fully prepared to pay a heavy price on the court. It was a lesson painfully learned by coaches and players who thought it might be smart to play mind games by undermining him in the press or to his face. Michael took any perceived slight and used it as additional napalm to feed his fire.

Some lesser people might choose to lob insults back verbally. But MJ always chose to do the talking on the court. With a memory of an elephant and the drive of a beast, Jordan came out swinging every time like a man possessed and never left the court till he made sure the opponent fully paid the price.

Takeaway: Find the triggers that ignite your fire. This could come in the shape of a less than favorable job performance review, a dream promotion you got passed upon, or a situation where you felt your good work is underappreciated. Take those negative moments and turn them into drivers to propel you forward.

8. SUCCESS IS A LIVING, BREATHING THING

“You’re only a success at the moment you perform that successful act” — Phil Jackson when talking about their quest for consecutive championships after the first one in 1991

Success for the Bulls didn’t stop with beating the Lakers in 1991. Once you get a taste of success, it becomes an addiction driven by the forward momentum you foster along the way.

Takeaway: Everyone uses a different set of criteria to define what success means. But we should all agree that success is better appreciated over the full arc of someone’s life and career.

9. FAILURE IS YOUR FOUNDATION:

Leaders view failure through a unique lens. They see it purely as the fire that propels them forward, as learning moments accompanied by a promise to oneself to do whatever is necessary to ensure the same mistake will never be repeated.

“I’ve never lost a game I just ran out of time.”Michael Jordan, For the Love of the Game

Takeaway: There will be many crushing defeats along the way. The resilience in dealing with failure is what sets apart successful people from those who get left behind. Churchill “Success is going from failure to failure without loss of enthusiasm.”

10. IT’S THOSE AROUND YOU WHO DEFINE YOU

Aside from the inspiring team of coaches and teammates over the years, MJ was blessed to have such an incredible support system over the course of his life and career.

Starting with parents who pushed and positively challenged him at an early age, and brothers who challenged him on the neighborhood basketball court where he first discovered first glimpses of his fiery competitive spirit.

When Michael looked back at his childhood’s one-on-one basketball games with brother Larry and often coming to blows at the end of it, he wistfully says “When you come to blows with someone you absolutely love, that’s igniting every fire within you” and he carried this fire forward for the rest of his career.

From a personal branding standpoint, Michael Jordan wouldn’t have been the $1.7 billion-generating powerhouse had it not been for master dealmaker David Falk, Jordan’s agent for his entire playing career and the one who dreamed up the Air Jordan concept for Nike as well as many other blockbuster endorsement deals.

Takeaway: Success is never a solitary journey. It takes a constellation of inspiring role models, mentors, and supporters to get to your final destination. Each and every one of them is deeply embedded in the mosaic that is your life and legacy.

There are those rare leaders whose accomplishments and influence rippled out far wider beyond their fields. Not only has Jordan transformed the Chicago Bulls into one of history’s best dynasties, but he undoubtedly elevated the NBA to a widely loved global brand.

In episode 10, David Stern waxed poetically about what MJ meant to the sport “In 1992 NBA was in 80 countries, and now NBA is in 215 countries. Anybody who understands the phenomenon of that historical arc will understand that Michael Jordan and his era played an important part in it”

Beyond the sport, Jordan indeed became a global Ambassador that embodies the best in sportsmanship, success, and entrepreneurship. He continues to be a marketing machine with his Air Jordan brand still thriving 17 years after his final retirement. And it feels like he’s just begun.

“There are great players who don’t have an impact beyond their sport. And then there are sports figures who become a larger cultural force. Michael Jordan became an extraordinary ambassador not just for basketball, but for the United States overseas” — President Barack Obama, The Last Dance

Couldn't have said it better.

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Sherif Shafi
The Startup

Life mysteries solver by night, Marketing tactician by day