Make your boss’s job easier.
Managing up isn't flattery. It's keeping your manager informed, aligned and able to support you when it counts.
No surprises
Bad news travels best early, and from you.
Problems with options
Bring the issue, plus two ways forward.
Know their goals
What are they measured on? What keeps them up at night?
Match their style
Short summary first. Detail when asked.
No surprises. Bring options.