This week I listened to a friend describe a proposal they’d been presented with. I recognized it as a classic “heads I win, tails you lose” scenario: the party on the other side from my friend would win regardless of the outcome. To be fair, these situations don’t always end badly: if the other party wins, you could win also. But if you lose, they still win.
I’m not a fan of this type of situation because of the misalignment of incentives. The other party is fine regardless of the outcome, so they usually have minimal incentive to push for an outcome that benefits you. This is different than a situation where your incentives are aligned and you win or lose together—in that case, the other party is much more likely to push for the outcome where you both win.
These situations are much more prevalent that people realize, but I do my best to identify and avoid being part of them.