Manage your boss by feeding them the right information at the right time

Aaron led a field team far from headquarters. He was tired of what he called “drive‑by oversight” whenever he sent in a plan. Emails came back with questions that felt basic to him. He vented to his team, and they rolled their eyes at “corporate.” The next approval took longer, not shorter. His coffee tasted bitter that afternoon, and he knew it wasn’t the beans.

He changed tactics. Two days before his next proposal, he sent his boss a one‑page pre‑brief: purpose, key tasks, top risks with mitigations, and the exact decision he needed. He added one line on how this served the bigger strategy and offered a quick call. The boss replied with three precise concerns. Aaron answered them and adapted the plan. When he presented it formally, there were no surprises, only a fast yes.

A week later, his team heard him say, “We debated this hard, and we’re aligned. Here’s the plan.” The grumbling faded because there was one clear story. After the job, he sent a five‑bullet after‑action note with outcomes and lessons. The next approval came even faster. It wasn’t that his boss had changed. Aaron had started leading up, reducing uncertainty and increasing trust.

This approach leverages perspective‑taking and uncertainty reduction. When you speak to what leaders care about before they ask, you lower their cognitive load. Pre‑briefs let you absorb objections privately and prevent showdowns. Presenting a united front downward preserves authority and stability. After‑action notes complete the loop, building a record that you are reliable and self‑correcting.

List what your boss watches most and tailor your updates to those risks and metrics. Send a one‑page pre‑brief with purpose, risks, mitigations, and the specific decision you need, and invite a quick call to surface concerns early. Once a decision is made, speak to your team as though you chose it yourself to protect unity. After the work, send crisp notes with outcomes and lessons so your boss never needs to follow up. Try this with your next proposal and notice the approval speed.