#15 Playing the Game

First, indulge me in a visualization:

Imagine you’ve woken up somewhere, but you can’t figure out where. 

As you come to, you get the sense you’re on a hard surface, but it’s a flat one, almost manicured. Green, but not grass.

There’s fences around you, some tall, and a short one in the green area.  White lines extend into borders as you stand to your feet. The wind blows. You hear sneakers and suddenly know what this is. You’ve seen this pace before. A light strung racquet is in your hand.  

Did you figure it out, Serena? You’re on a tennis court. 

Now, you’ve got three options, and only three. And this tennis court is a metaphor for everything: your life, your Wednesday, capitalism, the air you breathe. Everything. 

What are your three options? You can:

1. Leave. 

2. Complain.

3. Play. 

Note that only two of these options change your situation. 

The middle one is useless, and probably bad for your stress levels. (Plus, no one likes a complainer). So play some tennis, or go on and git! 

Earlier this week, a good friend reminded me how pernicious and subtle tennis (aka politics) can be.

Her VP and her exec have both shared a clear interest in one specific thing (to keep it anonymous, let's just say “scaling the org to keep up with a competitor”). It's what they recruited her on, interviewed her about, and repeatedly discuss in 1:1's with her. 

Per her style, she's consistently showed them how to do it. Yet, 6 months into the role, she's pitched plan after plan for what they want, only to get zero budget, no traction, and negative interest from the exec and VP. What gives?

What gives is what my friend Andrew calls, "wanting to want." 

A lot of what people talk about at work is NOT about what they want to happen, but rather, what they wish they wanted to happen. In reality, they want something else, and it’s either ego-hurting or inappropriate to admit.

Also, have you ever noticed how much talking about work can feel like work That’s wanting to want. That’s what everyone is doing on your tennis court.

Or, to put it another way, that’s politics, Baby!

Wanting to want is double-speak, and it’s hard to see through. To see what people really want. Whatever it is, you need to remember that people who double-speak also double-hear. Guess what that means for you.

They speak French in France don’t they?

In my experience, about 90% of the people on your court want only one thing: the status quo. The other 10% are hungry, for something. But it’s all the same game, just different prizes.

And that’s what’s so annoying about the tennis court of politics. Everyone is playing tennis, and tennis is insufferable!!

But hear me out. The word “politics” comes from the word “policy.”

“Politics” is just a contest to set the policy. The vision or processes that the people you lead will adopt. Set the culture, set the rules. Or keep the status quo.

Whichever, it’s YOUR policy. Or, it’s someone else’s, and that’s WHY we have politics. The word just has a bad comms team.

In reality, the practice of working with and through people to shape things is as old as humanity. Politics is fundamentally human.

And while everyone seems to agree it’s a bad game, we somehow all want good people to win it.

Which I’ll assume you are, and which leads me to section 2: how to win.

First of all, my advice is win. Play to win, and win.

Do you think Billie Jean King, or Muhammad Ali, or Bianca Valenti went out there just to make a point? Yeah, the point was they win. It still is.

They’re also proof that the ENTIRE goal of the game is to win the right to shape the game.

That’s an objective truth (suck it up), but this next part is 100% pure opinion:

I happen to believe, and metaphorically speaking, let’s say you’re a devoted pickleballer who wants to get playing times on an elite local tennis court—the absolute most expedient way to do it is to become the best tennis player.

Then you can have all the pickleballs you want.

(Also, before I try to think of a clever joke for this week’s share link at the bottom, the ONLY people you should send this week’s issue to are your friends who fight for pickleball.)

As many young founders in Silicon Valley learn, no one cares what you made. What we care about is how well you get everyone from the status quo to the thing you made. From, to.

That’s the game.

And remember, 90% of the players are on Team Status Quo. It’s not that they’re not playing. Some of them will kill to keep it.

So how do you win? Bob Iger says you should have a personal version of a political campaign manager. He’s right-ish, because this game has 10X complexity of chess everyone compares it to.

But here are a few broad rules for winning, humbly submitted from a couple decades of campaign management:

1. Study the rules.

This approach works best in large orgs, where the rules are less fluid. Charlie Munger says, “show me your incentives, and I’ll tell you your outcomes.” Look everywhere, but an easy place to start is the details of your perf process. Don’t search for loopholes you might use, look for what anyone else might use. 

For instance, you might notice it’s technically better to have a Level 7 salary with the bonus multiplier for top performance, than to have a Level 8 salary with a “meets expectations” bonus. That doesn’t mean you should just sandbag yourself to over-perform at a lower level. What it means is there are some people around you who have too much to lose to NOT do that. 

2. Be right, or better yet, not wrong.

This is for cofounder disputes. Situations where attorneys will be involved eventually, maybe years from now. The strategy here is always make extremely reasonable arguments. Good ones. Like a calm, smart lawyer. (And don’t lose your cool, or make any mistakes, ever.) The compounding this does to your leverage when the fight gets real is remarkable—you’ve won the war the minute your adversary’s attorneys start discovery. Because they are now telling your opponent—as his trusted advisors—to worry. You’re tempering their counsel. Also: keep records. Someone else’s sour grapes can be a fine wine to have in your cellar.

3. Pass back.

This is really helpful in middle management, but it works anywhere. It comes from my Dad’s friend Philip Baker who gave me advice as a (very) scrawny 13-year-old basketball player. “Anytime someone passes you the ball, get it back to them. They’ll only want to pass to you more.”

It is profound how widely this trick works. You’ll have to figure out what it means on your particular tennis court, but you should.

4. The choke chain.

This is for managing extreme high-performers. It is what it sounds like. Build people up as much as you possibly can, constantly. Support your directs and give them freedom on big decisions. And then, every once in a while, jerk that choke chain and remind them who’s boss. I won’t mention names, but this style is common to some of the most effective and successful CEO’s I’ve ever worked with—and incidentally some of the most pleasant. So please don’t assume this strategy is for A-holes. It actually seems the nicest C-somethings need to use it most.

5. Literally just change your clothes.

This is best for startups and small teams. It’s a funny thing about humans: we like people like ourselves, but too similar and they’re likable while not remarkable. Yet, too different from us and it’s hard to make sense of them. One fact all great sales people know is we really want someone who’s the same as us, except for only a few differences we really admire.

So all you need to do is dress the exact same as the other players. Then, you have this one remarkable differentiator from everyone else, which is how good you are at whatever it is you do. 

It’s that simple and as dumb as it sounds. But have you ever been to a tennis club? The best player is wearing the same stupid outfit as all the people whispering how great she is.

6. Quit.

This was always an option, but is never what you think. People who quit in protest are—oh shoot, I fell asleep thinking about the right word—forgettable. If you’re tired of the game, or tennis isn’t your thing, my only advice is to leave for something better. Find the company whose game you’re good at, or start your own.

But no matter what you do in life, eventually and inevitably, it will be a game.

And it’s all fun and games until someone loses an eye. Then, it’s just a game again, called Find The Eye.

Why? Because FINDERS KEEPERS.

Keep both of yours open for me,
Jesse

PS: Speaking of politics, here’s an interesting 2009 email thread between Marisa Mayer and Udi Manber, and their comms director Gabriel Stricker—all then at Google. Watch how Mayer and Manber communicate what they “want to want.” It’s subtle, with a wild epilogue.

PSS: I spent the weekend wiping noses (none mine) in a house of 4 with a cumulative body temp over 400°F. I also chatted with some AI models trained on real people, just fiddling around with Delphi.ai

For anyone curious, AI Keith Rabois might be even wiser than Real Keith Rabois, because he’s willing to talk to you about stuff Real Keith knows is stupid.

And AI Marcus Aurelius was surprisingly more helpful than conversations with AI Lenny Rachitsky, even if the socratic method is a terrible way to cook chicken.

PSSS: Due to the nature of this week's issue you may not actually want to share this one with your team. Winning is a secret sometimes better kept. But if you do share, here's a link. Pickleball!