How game theory applies to leadership, negotiations, and competition.

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Good Morning. You ever been in a situation where you had to choose between looking out for yourself and doing what’s best for the whole? That moment where trust and self-interest pull you in opposite directions, whispering in your ear like a devil on one shoulder, an angel on the other.

Welcome to the Prisoner’s Dilemma—a little game theory lesson wrapped in real-world consequences.

In today’s newsletter:

• We’ll explore the Prisoner’s Dilemma in business and leadership, expanding exactly how trust, competition, and strategic cooperation shape success, and why playing the long game beats chasing short-term wins.

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THE PRISONER’S DILEMMA

The setup is simple: two people commit a crime, they get caught, and they’re thrown in separate rooms. They can do one of two things:

1. Keep their mouth shut (cooperate with each other).

2. Snitch (betray the other).

What happens next?

• If both keep quiet, they get a slap on the wrist.

• If one snitches and the other doesn’t, the snitch walks free, and the silent one takes the fall.

• If both snitch, well, they both go down, just not as hard.

The logical choice? Snitch. The smart choice? Keep quiet. But trust ain’t easy when there’s a lot on the line.

Now, this little thought experiment isn’t just about crime and punishment. This is about business, leadership, and the way we play the game of life.

THE CORPORATE STREET FIGHT

Companies live in a constant Prisoner’s Dilemma. You got two options:

1. Play nice.

2. Go for the jugular.

Think of price wars. Two brands selling the same product. One drops their price. The other has a choice—match it or hold the line. If both keep lowering, profits nosedive. If one holds, they risk losing customers. If neither budges, they both win.

Or innovation. Do we share industry secrets to create something bigger than ourselves (hello, Tesla open-sourcing patents) or lock everything down to protect our turf (Apple’s walled garden)?

Play cutthroat, and you might win today. Play for the long haul, and you win tomorrow, too.

TRUST: THE GLUE OF GOOD LEADERSHIP

This isn’t just about companies. It’s about leadership, too.

A boss can choose to trust their team, empower them, give them space. Or they can micromanage, hoard information, and play dictator. One of those leads to long-term loyalty. The other? A revolving door of burnt-out employees looking for the nearest exit.

A team can collaborate or compete internally. Ever been in a meeting where people are more interested in looking smart than actually solving the problem? That’s the dilemma at work.

Great leaders trust first. And yeah, sometimes that trust gets broken. Sometimes you get burned. But the alternative? A world where no one bets on each other. And that’s a losing game every time.

BUSINESS PARTNERSHIPS: PLAY IT RIGHT OR PLAY YOURSELF

Nike and their suppliers. Tesla and Panasonic. Companies that make each other better when they work together.

A bad partnership is like playing poker with a cheat, sure, they might win this round, but nobody’s coming back to the table. A great partnership? That’s a long game. One where both sides leave a little on the table, knowing it’ll come back around.

Because winning once isn’t the goal. Winning again and again? That’s the move.

THE TAKEAWAY: PLAY THE LONG GAME

So what do we do?

• Trust first, but verify. Don’t be naive, but don’t be cynical either.

• Think past the next quarter. A quick win that burns a bridge isn’t a win at all.

• Build a culture of collaboration. Because when the whole team wins, everybody eats.

• Know when to be competitive. Sometimes, the right move is to go for the throat. Just make sure it’s worth it.

CONCLUSION

The best leaders, the best companies, the best people—they see the game for what it is.

Some folks are out here playing checkers. The real winners? They’re playing chess.

Checkmate.

Please share this newsletter with anyone interested in building foundational work cultures 😊😊

_{Written by Bailey Hepler}

ASK BAILEY

Yep, I’m now taking questions! Respond to this email with an office dilemma and I will include it in next week’s newsletter with my thoughts 🙂

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