[jaaron]

All the other comments note how risky the approach of giving feedback to your boss is, and they're right.

As a manager, it's on ME to setup the environment for candid feedback. It's something I have to emphasize over and over again and demonstrate very clearly and publicly to everyone that it's ok and it's what I expect.

If the boss isn't creating that environment, then it's a risky, uphill battle for any subordinate to create change. Not impossible, but it's difficult to recommend it.