Phil Jackson

Supported by Greenhaven Road Capital, finding value off the beaten path.

I don’t know what to do about Phil Jackson and his book Eleven Rings. Jackson won 11 NBA championships – hence the title – and that’s excellent. He also coached Michael Jordan and Kobe Bryant, two of the best players in the game. In an alternative universe, how many championships would Jackson have won had he coached the 1996 Knicks rather than the Bulls (and Whoopi Goldberg coached the Bulls)? How much of Jackson’s success was luck and how much was skill?

We don’t know.

Mark Suster wrote that he invests “in lines, not dots.” Suster wants to see patterns. How do founders act in meetings? How timely do they ship versions? How well do they adapt? Each action is a dot, many dots form a line.

That’s our spirit too. We look for patterns. If someone says decentralized command works, do we see it work in different domains like the military, education, and sports? What about arguing well? Bias busting?

It’s with this attitude I’ll make the case for Phil Jackson as a great coach because he does things other great leaders do too. Ready?

1/ Lead from the outside in. Don’t run with the lemmings, Jackson writes, you need to act like you. Warren Buffett said that Berkshire wasn’t going to try to out Bezos (Jeff) Bezos. You’ll never imitate your competitor better than they can be themselves. So, you may as well be you. (This is good!)

You are your competitive advantage. Harry’s didn’t try to become DSC. Why? Because Dollar Shave Club is better at being Dollar Shave Club.

Do you know why sharks still exist? Becuase nothing is better at being a shark than a shark. – Douglas Adams

Seth Rogen and Evan Goldberg say they are best at writing, so they write. Tren Griffin asks if you are a moat builder or identifier. David Chang started Momofuku because that what his advantage.

Jackson opens the book with this quote from Rumi, “When you do things from your soul, you feel a river moving in you, a joy.” Part of the reason people succeed is because they don’t imitate something that works for someone else. Jackson coached in a way only Jackson could coach.

2/  Constraints help. “What attracted me to the triangle (offense) was the way it empowers the players, offering each one a vital role to play as well as a high level of creativity within a clear, well-defined structure.”

Constraints help for two reasons.

  1. The paradox of choice. People tend to not do well with too many choices. Supermarkets that display more sample sell less. More choice means more work (and System 2, points out Daniel Kahneman, is comfortable on the couch).
  2. Necessity is the mother of invention. Constraints beget more creative movies. Constraints beget better art (Sistine chapel). Constraints beget better countries (and avoid the resource curse).

Jackson thought the triangle offense could offer this on the basketball floor. It was the hardwood version of Jocko Willink‘s mantra that “discipline equals freedom.”

3/ Chaos monkeys.  Jackson used a light touch on his team, but sometimes, “I like to shake things up and keep the players guessing.”

That meant practicing in the dark or in silence. It meant games of five on four where the team of five was allowed to grab, push, hold, and cheat. It meant odd detours on road trips. It meant occasionally getting in someone’s face. It meant randomness.

Netflix has the chaos monkey. Nassim Taleb has randomness. Jeremiah Lowin drops data. Anson Dorrance scheduled long road trips and showed up at the last minute for a game. Rorke Denver suggested “random acts of violence.”

“There is also a lot of value in a certain kind of distration which can lead to accidental discoveries.” – Sanjay Bakshi

All these leaders built resilience. The system crashed? So what. My pregame rituals got disrupted? Happens all the time. I don’t feel like it? I never feel like it.

Crazy stuff happens, chaos monkeys prepare you for it.

4 / When in doubt, do nothing. “Basketball is an action sport, and most people involved in it are high-energy individuals who love to do something – anything – to solve problems. However, there are occasions when the best solution is to do absolutely nothing.”

Most of Jackson’s media interactions and player interventions were this hands-off approach. We (and by we, I mostly mean me) are so tempted to act because we think in linear terms. A causes B because B follows A!

This isn’t always the case (“In fact, it’s rarely the case”).

In the early days of NASA, the default was to do nothing. Gene Kranz wrote, “the first rule of flight control is if you don’t know what to do, don’t do anything.” Don Keough warned that doing something just because you can do it isn’t a good enough reason.

“Action is easy, thought is hard.” – Goethe

5 / Be a learner. Jackson tried to nudge his players (the indirect approach) into new approaches to the game by giving them books. Jackson has always been a learner (see #1). “Playing for New York during the championship years was like going to grad school in leadership,” Jackson writes. Later on when he was hired as a scout for the Bulls, “this job was a chance for me to go to graduate school in basketball.”

Systems atrophy without attention. We are all part of systems. It could be your ecosystem, your team, your organization, your Slack group, or your industry. Uninfluenced, each system will disintegrate. What keeps our system, team, group, family, organization running is us keeping it running!  We must fight against atrophy. Learning is one way to do that.

6/ Argue well. “What impressed me about Bill (Bradley) and Cazzie (Russell) was how intensely they were able to compete with each other without getting caught in a battle of egos.”

Micahel Jordan said about some early disagreements with Jackson, “It took me a while to calm down…(but) but our mutual respect grew.” There were some larger blow-ups, some that included blows, but Jackson’s teams mostly argued well.

When his teams didn’t argue well and manage situations well they were defeated. This is easy to see in business. Andy Grove titled his book, Only the Paranoid Survive. Peter Lynch warns investor to do the work or don’t enter the game. If an organization – like a basketball team – fails to argue well they will be passed by competitors who do.

To argue well you need the right culture. It’s why Marc Andreessen takes the opposite side of Ben Horowitz in arguments. That creates an environment (read: culture) where employees aren’t pressured to align with the boss. Bill Belichick does the same thing. Patriot staffers were rewarded for coming up with good and different ideas.

7/ Deep understanding.  “Johnny would often show up at my desk with dog-eared books by coaching geniuses I’d never heard of and videotapes of current NBA teams using moves invented years ago.”

Despite Jackson’s real-life experience (#5) with the Knicks and Bulls, he still had to rely on others. One of those was an encyclopedia-like assistant. This was true for Bill Belichick, who has Earnie Adams. Both Jackson and Belichick have someone else who understands history. This is how and why it’s been done and what the first answer might be.

Mohnish Pabrai said that Buffett is excellent at learning from others. That’s what Jackson and Belichick try to do. Sam Hinkie addressed this in his resignation letter. How do you balance being different with doing what works? You have to have a deep understanding. Hinkie wrote:

“While contrarian views are absolutely necessary to truly deliver, conventional wisdom is still wise. It is generally accepted as the conventional view because it is considered the best we have. Get back on defense. Share the ball. Box out. Run the lanes. Contest a shot. These things are real and have been measured, precisely or not, by thousands of men over decades of trial and error. Hank Iba. Dean Smith. Red Auerbach. Gregg Popovich. The single best place to start is often wherever they left off.”

Understand deeply.

8/ Two-jar model.  “I believe if you’ve taken care of the details, the laws of cause and effect – not luck – will usually determine the result.”

That quote addresses the two-jar model so well. Let’s summarize what Michael Mauboussin and Jackson write.

  • There are two jars we draw from for any outcome.
  • One jar includes our range of skill scores.
  • One jar includes a range of luck scores.
  • We can raise our skill scores through deliberate practice.
  • We cannot change the luck scores.
  • With enough work, we can raise the skills scores so high, they offset any luck score we draw.

The skill jar for Jackson’s teams included; footwork, spacing, passing, leadership, and even a chaos monkeys (#3).  “We focused most of our time on things we could control,” Jackson writes about practices.

Thanks for reading. If you liked this post, you’ll probably like the series on Bill Belichick.




12 thoughts on “Phil Jackson”

  1. […] Despite these two drawbacks – mistakes of omission and commission – filters remain helpful because they create detachment. This is a key leadership trait says Jocko Willink. Detaching from your position means a decision maker can be more empathetic, an important part of negotiations and coaching. […]


  2. […] Phil Jackson wrote, “One thing I’ve learned as a coach is that you can’t force your will on people. If you want them to act differently, you need to inspire them to change themselves.” At CAA this wasn’t infrequent and led to some interesting what-ifs, like if it wasn’t Cruise and Hoffman in Rain Man. Another was that Bad Boys was written for Jon Lovitz and Dana Carvey. […]


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