Great CEOs are Really Coaches, So Let’s Learn from Phil Jackson

“I don’t care if it’s 82-and-0 this year, you’re f***ing gone.”[5]

– Jerry Krause, Owner of Chicago Bulls to Phil Jackson, The Greatest Coach Ever, After Phil Jackson Won His 5th NBA Championship, and just Before He Went On to Win His 6th NBA Championship and Thereafter Retire.

That’s quite a quote.

In light of the Lakers’ stunning decision to not bring Phil Jackson back (which apparently stunned not only Kobe Bryant, Magic Johnson, but even Phil Jackson himself), I wanted to learn more and what made him such a great coach.  The Greatest.  Coach.  Ever.   11 World Championships as a Coach.  The Winningest Record Ever.

And why the owner of the Bulls would say such a thing in between winning two world championships.

And how it applies to being a SaaS CEO.

Because being a CEO is in large part like being a coach.  Especially once you get out of the very early stages (> even just $1m ARR) and need to/should stop doing everything yourself.  In fact, being a CEO is being a coach.  Period.   You recruit.  You manage.  You put a team on the court.   And you empower, trust and manage them to do the best they can.

So let’s try to analyze some of the things Phil Jackson did so well, because Managing Up clearly was not one of them:

>> First, how did he get there?

  • He Did It, and The Hard Way, as a Player.  Phil Jackson spent five years on the bench for the Knicks before he started.  He won two NBA championships, but as a reserve, not a starter.  He missed the ’70 championship for the Knicks entirely due to back surgery, and had to cheer from the bench.  Great SaaS CEOs learn how to build software companies the hard way, in the trenches as individual contributors and then team leads.  It’s really hard to fake it in SaaS.
  • He Was Tenacious, Always, and Stayed Focused on Getting There.  And He Paid His Dues.  Phil Jackson started as a coach with the Albany Patroons.  Heard of them?  Probably not, but he lead them to their first CBA title.  He sought an NBA job again, and again, and was turned down again and again.  Did he quit?  No.
  • He was Ready to Step Up.  When he finally was hired as an assistant coach by the Bulls in ’87, he was ready when Doug Collins left, and was the default choice for head coach in ’89.
  • He Sought Out Great Mentors to Learn From.  His switch to his famed triangle offense was due, apparently, to methodically reaching out to every winning coach in basketball, and then becoming a devotee of Tex Winter’s triangle offense.
  • He Knew The Difference Between Good and Great.  Phil Jackson took advantage of the fact he was a good, but not a great NBA player.  It’s liberating in fact, to not be the best and to be comfortable with that, but to play with the best, if you are a student of the best.  “Here’s the thing. If I were Bill Russell, and there were eleven championships and I’d been the MVP five times, I might have a vaulted opinion of my own self-worth.”  Most CEOs are not the best at any individual function.  You need to be pretty good at several though, to know how to hire the great ones.

>> Then, How Did He Win So Often, and So Well?  And Why Was He Basically Fired Twice, Almost Thrice?

  • Once He Earned It, He Was Supremely Confident.  Tensions grew with the senior management staff of the Bulls, even as the World Championships came in.  An unprecedented three-peat.  But the Bulls’ GM and ownership thought they deserved more of the credit.  Maybe this characteristic isn’t really all 100% great, but it comes with the territory.
  • He Couldn’t Stay Away.  Winning was His DNA.  Phil Jackson retired after the ’88 Bulls championship, vowing never to coach again.  But he couldn’t stay away from the Lakers.  And then when the Lakers imploded, they lured him back agan.  He Couldn’t Stay Away.  Winning was his DNA.
  • He Found a Way to Manage Multiple Superstars.  The bottom line is Phil Jackson had great players, the best — but Chicago only won championships once Phil Jackson was coach.  And the Lakers only won once Phil Jackson was the coach.  Great Coaches and CEOs have to learn to manage multiple egos, not sublimate them or avoid them.
  • He Learned from the Status Quo, But Had No Problem Challenging It and Improving It.  “Jackson was such a maverick that in 1975 he wrote a book called Maverick, rather a guide on how not to have a future in basketball, which included his pronouncement that he would never be an NBA coach because he couldn’t deal with the egos.”

>> What Were His Management Strategies?

  • He Empowered His Team To Figure It Out On Their Own.  “‘His philosophy was always, ‘You guys need to figure it out on your own,’ and that’s what made him a phenomenal coach, is that he was able to sit back and trust the process, trust the players to communicate with each other.”
  • He Was Zen About What He Could Not Control.  CEOs have way too many decisions to make as it is.  Fretting about what you can’t control depletes you and destroys you.  “[Jackson] taught me how to deal with these types of situations,” Bryant said. “I wouldn’t be disappointed. I’d just be, which is what he taught me”.
  • He Found a Way to Shake it Off, Eventually.  When Jackson was fired/left the Lakers after 3 world championships, he blamed Kobe.  And it was Kobe that wanted him back in 18 months, and in 2012.  “I didn’t know Phil was going to be an option … they said, ‘Well, it is, and I want to know how you feel about it.’ I said ‘I love it,’ and that was it.”
  • He Taught.  Orders have their time and place.  Teaching moments though last a lifetime.  “He teaches us the little nuances, the details, the intricacies of the game that just a lot of people just don’t know.”
  • He Genuinely Admired His Team.  As CEO, your team needs to look up to you.  But you need to strive to have a team you are simply utterly impressed by.  The two-way respect of 100% commitment on the part of everyone, on a great team.  “I must confess to being spoiled by Michael’s leadership and by his ability to rise to every competitive occasion.”
  • He Loved It.  It’s a dirty secret, but a lot of SaaS CEO don’t love their job.  They may be very good at it, but SaaS is hard.  It’s a grind.  It burns you out, as the years go on.  But the great ones love it.
  • Trust.  Mutual trust.  Earned.

Understood that this is only a partial list, but I picked the pieces I felt most applicable to SaaS CEOs.  I think it’s a good list ;)

Pic from here, table below from Wikipedia.

2 comments

  1. Brendon Cassidy

    If you haven’t read it, read the Jordan Rules. Great book. And it shows Phil’s process before Phil was famous for it, and before Phil could show his rings for credibility.

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