Why is it that everyone wants to be manipulated.

"Shooting the messenger" may looks like it hurts the other guy more but I've seen it screw up entire reporting hierarchies. By the time things go off the rails nobody higher than a level 1 manager has any damn clue what really happened, although they think they do based on the misinformation they've been fed.

Keynesian beauty contest? A VC may personally appreciate a member of his portfolio showing weakness, but also assume that his peers won't.

I've had bosses who loved hearing bad news. And bosses who were great about bad news as long as they were the first to hear about it.

Nobody likes to get called out in a meeting about a problem they are responsible for but know nothing about. That's probably the weakness thing again.