Ever heard of the Prisoner’s Dilemma?

It’s this classic scenario where two people have to decide: do they trust each other and cooperate, or betray each other to try to come out on top?

Most of the time, they choose to betray out of fear, and guess what happens? They both end up worse off than if they had just worked together.

Sound familiar?

In real estate deal-making, it plays out the same way. We’re often so focused on getting the best terms, the biggest cut, or the perfect piece of property that we don’t realize we’re trapped in our own version of the Prisoner’s Dilemma. We think, “If I don’t push for this advantage, the other party will, and I’ll lose.”

I’ve seen it firsthand. Negotiations where both sides are trying to “win” end up stalled, relationships are strained, and deals fall through. But when both parties trust each other and focus on collaboration, you can unlock opportunities that wouldn’t have existed in a win-lose approach.

That’s the real lesson of the Prisoner’s Dilemma. You can either play the short-term game and focus on squeezing every last drop from the deal, or you can think long-term, build trust, and end up with something bigger than you could have on your own.

Have you ever been part of a deal where collaboration led to a win-win outcome?