I met my sergeant soon after I arrived in Germany. His name was Thomas Brett. I was a green, newly minted, Second Lieutenant placed in charge of eight Medical Dispensaries. I knew just enough about being an Officer with such responsibility to easily get myself into trouble.

It quickly became obvious to me that Sergeant Brett’s responsibility was to take me under his wing, teach me the ropes, and educate my instincts before I launched any major exercise of my authority. The tact and diplomacy with which Tom accomplished this mentoring feat never left me thinking that he, not I, was the boss. 

In business and the public sector, a subordinate generally will not have as much experience as their superior. That does not mean, however, that one’s boss isn’t lacking in some area of experience or insight that you possess.

Helping your boss to succeed, generally will help you as well. But it takes the sort of tact and diplomacy that Tom Brett displayed not to appear disrespectful, condescending, or acting beyond your pay grade.

Some bosses will refuse to listen or heed your counsel no matter how diplomatically it is presented. Nevertheless, while always a judgment call, thinking about how you might mentor your boss effectively so as to further their and your objectives is a worthy endeavor.

There is a phrase widely used to describe some bosses: “hit the ground running”. It always makes me laugh. I am a highly pictorial thinker. I picture such a manager parachuting into their job with their legs pumping full tilt. The minute they hit the ground, off they go. Unfortunately, there are 360 possible degrees in which they can run, a good 300 of them representing the wrong direction.

This is precisely the sort of boss who will need wise and cautiously given advice to prevent early mistakes effecting you and many others. Equally in need of some diplomatic intervention, are those bosses who are determined to demonstrate they know it all before they know it all or who never seem to listen period. Mentoring these superiors is far from easy but managing up in general is a challenge even with the most cooperative boss.

Figuring out what motivates a boss, influences their actions, enables them to both over and under-achieve, and at times makes them seem like they are determined to drive you crazy, that is the very essence of a prerequisite for mentoring up. If you think you’re up to it, give it a try.

UPDATED April 2026

Categories: Exercising Responsibility, Managing & Leading, Managing People

Tags: advice for managers, effective management and leadership, effective managers and leaders, management advice, Managing & Leading, managing up, Self-Management