So here’s a basic philosophy of mine regarding briefing the boss bad news. Bad news does not get better with age. If your boss finds out something from a source other than you, you end up looking like an ass. More than likely, if you’re trying to hide a problem, the boss is really going to have kittens when he does finally figure it out.
The best course of action when dealing with bad news is figure out what’s going on, come up with a plan, and brief the boss on courses of action that will get the problem solved. Waiting until it’s a crisis isn’t proper management.
I’d love to hear other thoughts on how to manage and break bad news and different points of view. Always up to learning something new.