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Making the Boss a Success May 13, 2025

by Peter Martini

“We failed him,” said our Command Sergeant Major when our organization’s commander was not selected for promotion. In an instant, I moved from empathy to introspection and began a journey of asking, “Am I responsible for my boss’s success, and, if so, how can I help my boss succeed?”

Here are three common situations that bosses encounter and ways in which we, as contractors, may assist.

Principle: Communication is bidirectional.

Use case: My boss doesn’t have … Create it! In many cases when something is lacking, it can be drafted for the boss and provided upward. Waiting on a policy decision? Draft a Course of Action paper with options and recommendations. Can’t get a meeting with another office? Draft an email for the boss to send to set the ball in motion. Don’t let absence prevent action.

Principle: The Area of Operations is not the only area to consider.

Use case: My boss doesn’t know … Find out! Extend spatial awareness beyond the Area of Operations to the Areas of Influence and Interest. Think of it as networking in 3D. Your boss must consider the “manager once removed.” So, start with what the boss of the boss’s boss needs. Look at the problem from the top down and outside in.

Principle: Time doesn’t bend, but it can be stretched.

Use case: My boss is constantly reacting … Think strategically! A key aspect of increasing seniority is an extended time horizon (i.e., the maximum time allocated for any assigned task). Reactive experiences often stem from planning that is too short range. Encourage the boss to take a longer view.

Then, avoid surprises and prepare the boss for a promotion.

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