Comment by SpicyLemonZest

> This seems tautological to the point where it's meaningless. It's like saying that if you try to hire an employee that's going to challenge you, they're going to always be a sycophant by definition. Either they won't challenge you (explicit sycophancy), or they will challenge you, but that's what you wanted them to do so it's just another form of sycophancy.

I think this insight is meaningful and true. If you hire a people-pleaser employee, and convince them that you want to be challenged, they're going to come up with either minor challenges on things that don't matter or clever challenges that prove you're pretty much right in the end. They won't question deep assumptions that would require you to throw out a bunch of work, or start hard conversations that might reveal you're not as smart as you think; that's just not who they are.