The Chess Master and The Gardener

I love listening to podcasts to entertain my commute. I’ll at least learn something if I’m going to be stuck in traffic 200 hours a year. One of my subscriptions is the Tony Robbins Podcast, featuring the motivational guru interviewing a myriad of successful individuals. A recent episode that really resonated with me is a chat with General Stanley McChrystal and Chris Fussell, titled “Becoming an extraordinary leader“. The interviewees served in the U.S. military for decades and have gained some insights into great leadership. An analogy the General used to describe leadership was the chess master and the gardener.

I’ve always had the impression of military leaders as tough, disciplined warriors who would snap your neck if you even harboured a sense of disagreement. General McChrystal’s early career hinted at that power structure. Note: numbers in [square brackets] indicate the minutes and seconds into the podcast that the transcript begins.

[08:45] I thought that leaders were a command-and-control function. You got information from across your organisation, you use your experience and what intellect you had and aided maybe by (unclear). You made decisions and then you directed those decisions down into the organisation to comply. And if you were a better strategist than your opponent, you would win.

That’s certainly my assumption about the military. I’ve met similar leaders in my IT career. The General understands the temptation.

[14:15] There’s also a human side to it as well. When someone’s put in charge of an organisation, as a leader they think that they’re the best qualified person to make decisions. They’re going to be held responsible for the outcomes so there’s a tendency to want to make the decisions that determine it.

This is where the analogy of the chess master and the gardener comes in. It was mentioned in his book and he summarises it in the podcast:

[47:00] For years I thought that chess master was the best analogy to a successful leader because a chess master controls 16 chess pieces and moves them. And if he or she is a good strategist, they win. And they’re micro-managing each of those chess pieces.

When I got into Iraq I started that way, and then I found that out my opposition Al-Qaeda in Iraq was not a chess master controlling pieces - it was a set of chess pieces that all connected and had relative autonomy. So as a consequence there’s no way one person can defeat a multiple group like that that’s constantly adapting.

So slowly … I realised that gardener is a better analogy for it. Because if you think what a gardener does, a gardener doesn’t grow anything. Only plants can grow things. But the gardener is critical, because the gardener creates the environment. The gardener prepares the ground, the gardener plants, waters, feeds, weeds, protects, and at the appropriate time, harvests. If the gardener does it right, all those plants can do that concurrently, and so suddenly you can scale.

The gardener is completely busy. It’s not a case of empower your subordinates, go home, and let me know how it works. You’re constantly protecting the garden so the garden’s plants are able to do it. And so I believe it’s a less ego-centric way of leading. It takes a little bit of courage to do it because you are allowing your entities to execute. There’s always a chance it’s not going to come out and you’re going to be held responsible. But it’s in my view the only way that will operate in an environment that is changing fast. And it also has the added benefit that people who are doing it with you feel like they are part of us. They don’t feel like they’re employees of the leader.

The gardener analogy really struck me as something profoundly straightforward but also difficult to practice. I definitely didn’t expect that leadership style from a four-star general! One example that illustrates his ‘gardener' approach was:

[23:00] My requirement was to be a connector. My requirement was to move around the organisation, orchestrate conversations, [and] create connections. Much like Steve Wynn did, we did a daily teleconference across the entire command and I was sort of the ringleader for it. I didn’t make a lot of decisions or give guidance but I would make sure that people across the organisation who didn’t know each other and think they had shared equities were connecting because we’re trying to defeat a networked enemy.

The almost 90-minute long interview goes into a lot more detail and I would recommend listening to it in chunks. That is because the interviewing style gets a bit dry without fancy sound editing to avoid audio monotony. It has lots of great content that becomes food for thought.

So: are you a chess master or a gardener?