Protect the Relationship

After giving upward feedback, monitor the aftermath. Watch for signs that your boss appreciated it or felt threatened by it. Feedback that points to a specific behavior, rather than a personality trait, is far easier to act on and far less likely to wound.

Sometimes the wisest communication is strategic silence. If your boss is under extreme pressure from their own leadership, adding criticism from below is poor timing regardless of how valid your point is. Knowing when to hold a point is itself a feedback skill.