Ditto. Empathy is important...I imagine that boss, if he's relatively young, has to deal with the pressure of seeming like an effective boss, and that includes setting some hard lines...because let's face it, the boss and employee can see eye-to-eye, but that understanding doesn't always communicate across all the other employees, leaving some resentful. It's not dysfunction, necessarily, it's just the nature and friction of having an understanding and an implicit agreement. And so having a hard-no-compromise rule is sometimes easier. And younger bosses do worry about not wanting to seem like a slacker millennial (to their bosses)