Zen and the Art of Winning: Phil Jackson’s Team Leadership

Phil Jackson won 11 NBA Championship rings as a coach—6 with the Chicago Bulls and 5 with the LA Lakers. He’s the most winningest, successful coach not only in NBA history, but in the history of professional sports the world over.

A maestro of managing egos, Jackson got people like Kobe Bryant, Shaq, Scottie Pippen, Michael Jordan and other alpha maniacs to subordinate their talents to the goal of a better team.

His Zen leadership style was wildly successful on the court. It provides no shortage of food for thought when it comes to work and real life too.

Leading by Zen: the no-ego team

If you’re someone who makes a living in tech, in one way or another, you may well have some, ahem, triggering memories of gym coaches.

Long story short, the psychology of sports leadership is often not geared towards respectfully influencing team members, building up character, and teaching tolerance and mindfulness. It’s more often about intimidation and coercion, getting people to fall in line and perform for fear of failure, ridicule, termination, or “atomic wedgies.”

Other times, it’s all about putting the pressure on, to “win one for The Gipper.”

In all fairness, the ‘gym coach’ nightmare is a pretty extreme manifestation of the “alpha leadership” archetype. Sports, particularly as they ascend the ladder to the highest professional levels, are some of the most hyper-competitive areas of human civilization.  

But it’s incontrovertible fact that the alpha leadership model—so favored by the vast majority of sports coaches—is also the predominant one across Western culture, from business to education. It just varies in intensity.

Phil Jackson is a different sort of animal

“After years of experimenting, I discovered that the more I tried to exert power directly, the less powerful I became. I learned to dial back my ego and distribute power as widely as possible without surrendering final authority.”

He leads, and succeeds, with a leadership philosophy built on a foundation of meditation, mindfulness, and Buddhist ideas. His real-world application of Zen is one of the most fascinating going.

Born in 1945 in Deer Lodge, Montana, Jackson was raised in a very, very Christian household. His Pentecostal parents gave him a sparse, reserved midwest childhood, with no TV and no movies. He was well on the way to being a minister, just like everyone figured he’d be.

Then fate took him down a completely different path.

Turned out he was pretty good at basketball. He won two state titles with his high school varsity basketball team, which got him scouted to the University of North Dakota’s team. In 1967, he got drafted into the NBA by the New York Knicks, who won two championship titles with him on board (in 1970 and 1973).

While he was never a powerhouse player, Jackson was intelligent and determined. Fans liked him; teammates respected him. The qualities of character and strategy that animated his coaching philosophy were already apparent.

Jackson retired from play in 1980 and floated around as a coach in lower-tier professional leagues until 1988 when he was hired as the Assistant Coach for the Chicago Bulls. In 1989 he moved up to become Head Coach and quickly whipped them into a championship team.

He won, a lot. He clinched the NBA Championship Title a whopping 11 times over 20 seasons, as indicated in the title of his 2013 book, Eleven Rings: The Soul of Success. 

With the Bulls, he won six times in two seperate 'three-peat' runs (the first such feat since the Boston Celtics won 8 championships in a row with legendary head coach Red Auerbach from 1959-1966). In the 1995-1996 regular season, the Bulls posted a record-breaking 72 wins and 9 losses (Golden State squeaked past this milestone with a 73-8 record in 2015-2016).

Moving to the Los Angeles Lakers in 1999, Jackson immediately did another three-peat champsionship run, followed by two more wins in 2009 and 2010 towards the end of his career.

He left his NBA coaching career with a jaw-dropping .704 winning percentage, the highest ever. And he did it all... with Zen!

Well, to be fair, it was Zen in the main, with a dash of humanistic philosophy and Native American cosmology as support.

In any case, his material world success further dismantles the idea that Zen is an inscrutable Eastern philosophy—or a trend reserved only for new-age types and academics.

The Jackson model sees power withheld and delegated. Team members are encouraged to grow, coaxed to find their own answers to the problems that beguile them. The goal is to bring everyone into harmony and oneness.

“[Leadership is] a mysterious juggling act that requires not only the thorough knowledge of the time-honored laws of the game but also an open heart, a clear mind, and a deep curiosity about the ways of the human spirit.”

Jackson’s leadership provokes a lot of soul-searching about the alpha leadership we’re familiar with as Westerners. His style is a lot different than that of the energetic, assertive figure leading by example, giving orders and whipping the troops into shape with good old fashioned discipline.

Lending Siddhartha to Shaq: team leadership riding on winds from the East

One of the most amusing examples you can find of Jackson’s idiosyncrasies is his practice of giving personalized books to players to read. Particularly when said book-giving involves handing a copy of Herman Hesse’s Siddhartha to Shaq and asking him to turn in a book report.

Hesse’s fictionalized account of the life of the Buddha tells the story of how young Siddhartha gave up his gilded princely life for a selfless, spiritual quest for enlightenment. Jackson assigned the book because he felt Shaq was being too materialistic.

Shaq didn’t give up his high-powered lifestyle and run off to a Tibetan monastery, but he did get the book’s angle on compassion. He became more generous with teammates, and more empathetic in general, according to Jackson.

Fun fact: apparently Jackson had earlier lent Shaq Ecce Homo, the final book by Nietzsche, everyone’s favorite German philosopher. Shaq didn’t actually read it but looked at Cliffnotes.com to get the gist (the gist being, tone down the self-doubt and wackiness, Shaq, or risk Nietzschean insanity).

Jackson drew quite a bit of ribbing from the NBA world at large for incorporating mindfulness meditation into his pre-game ritual. His strategy for dealing with teamwork intangibles—all those minute issues that seem impossible to articulate in words—came off to many as silly and eccentric.

But, of course, it worked.

One Team, One Breath 

Jackson started doing his famous "One Team, One Breath" policy when he wanted to bring consciousness and mindfulness to the LA Lakers. He brought in a person that taught meditation through the University of Massachusetts’ medical system, as recommended by famous American spiritualist Jon Kabbat Zinn, author of the 1994 mindfulness popularizing text Wherever You Go There You Are.

In pre-game sessions led by the UMass mindfulness teacher, he would have his team practice deep breathing in unison, getting them to sync all of their breaths as one.

Of course, such oneness was not always achieved, given the incredible egos involved.

Following a game when Michael Jordan single-handedly ran up the score and clinched the win for Jackson’s Bulls, assistant coach Tex Winters quipped to the star player that “there’s no ‘I’ in team,” to which Jordan replied: “but there is in ‘win.’”

If mindfulness exercises occasionally fell short of their ideal outcome, Jackson still saw them as incredibly useful. They were, if nothing else, a very accessible means of calming the everywhere-at-once chatter in his players’ heads, putting attention on the present moment. Since mental exercises were not part of the NBA curriculum at all, he gained a distinctive psychological advantage by increasing his team’s ability to focus single-mindedly.

In the NBA, mindfulness is important because the game is chaotically fast and the pressures on players are extreme. In real life, it’s important because the practice can help us get a handle on ourselves, and stop going into a tailspin or endless series of tangents.

Of course, lest we think Jackson’s strategy is all about holding hands and feeling terrific, Zen Masters like him also know how to use “the stick.” In old-school temples, falling asleep during meditation will result in a whack of the “compassionate stick”, also known as a keisaku.  Jackson was not above using such methods, even if the vagaries of the American legal system prevented him from literally whacking his players into submission.

Some of the more bizarre disciplinary things he’s pulled on teams include: forcing them to scrimmage with the lights turned off and making them practice in complete silence.

Perhaps most cruel of all, he also used to sometimes divide his teams by weak and strong, then call no fouls on the weaker team. When the weaker team invariably started to win by a huge margin, he would stand by and watch the stronger team’s pained, incredulous reactions.

I can only imagine Jackson’s enormous schadenfreude at watching egomaniacs Kobe et al. being taken apart by foul-playing and—I like to imagine—foul-mouthed benchwarmers.

Mr. Jackson, you can be quite the devil.

Incorporating Jackson’s lessons on a team that doesn’t include Kobe

“Sometimes I sits and thinks, and sometimes I just sits.”

      — Satchel Paige, quoted in Jackson’s Eleven Rings of Success

When it comes to applying Jackson’s lessons in your own organization, there are a bevy of takeaways. More than you can shake a “compassionate stick” at.

To begin with, there’s one of his main, very simple yet powerful lessons: leading a team is a fluid process, and “you have to follow your intuitive nature.”

True leadership is about learning to lead “from the inside out,” and being authentic with your inner voice. That takes time, and self-examination. Bitter truths will need to be borne, dirty laundry will need to be aired, and criticisms of the self-administered and external variety alike will need to be accepted.  

The issue of “being authentic” extends to trusting your gut when it comes to assembling your team. Jackson feels that you have to look at someone’s attributes for what they are. Even if someone has many desirable characteristics, if there’s something “off”—if they just don’t fit into the framework you’re building—you’ll have to say no to them.

In job world parlance, that may mean that it’s better to hire a go-getter upstart lacking experience, rather than a demanding veteran with a bad ‘tude.

On the other hand, as Jackson’s positive results with Jordan, Shaq, Bryant, and other “difficult” personalities show, true leadership can iron out a lot of kinks.

By guiding people in a non-patronizing way, nurturing them to be their best self at work, it’s possible to put some problematic types on a better path. When one person improves, it strengthens the entire team.

Elsewhere in Jackson’s Eleven Rings, he speaks of mindfulness as an antidote to spiritual malaise.

In his book, he’s referring specifically to the “soul-deadening” NBA experience of a new game and a new city every other night. But this feeling of placelessness is perhaps just as valid when it comes to those of us working in a screen environment all day, particularly if you work remotely.

We’re all over the map, in one sense, but we’re not really anywhere. To overcome the cognitive overload of short attention span multi-tasking, and the potential loss of purpose that can afflict us, it makes sense to turn to mindfulness and meditation exercises.

Another great takeaway is Jackson’s nonchalant attitude to winning and losing. He was once asked by a reporter, after a game he had lost, what he would do after leaving the arena. Then he was asked what he’d do if he had won instead. His answer was the same for both scenarios: go home, have a drink, and eat the dinner his wife had prepared for him.

This is sage wisdom for endurance in working life. We’re going to lose, a lot, even if we win a lot. Big entrepreneurial success stories like Jeff Bezos and Elon Musk know and accept this, and we should too.

Being able to stay on an even keel prepares you to deal with the highs and lows of life, either of which can blow you out of sync and cause intractable problems long-term.

Authentic leadership, authentic success

Leadership is tough stuff.

Most of us have experiences of being led by managers who, although well meaning, ultimately don’t have any visionary strategy. They didn’t know how to read people on the team individually and be authentic with them. Or worse, they weren’t curious and they didn’t really care.

Jackson’s lessons show that the best team is one where everyone, including leadership, does care and enjoys the experience, win or lose. It’s a tribal way of looking at team building, where responsibility, empathy, and compassion are seen as deeply important.

Life’s bigger than a few egos, after all.

Mindfulness is one great tool for reaching this state of unity on an individual level, allowing us to find time for quiet contemplation. Mindful leadership can allow us to find success in a way that’s meaningful, authentic, and sustainable.

By leading in a way that animates a near-spiritual sense of team unity, you distinctly increase your chances for success without forcing it.

Because sure, success is great, but succeeding authentically is one of the sweetest things out there.