When You Think It’s Time To Tell Off Your Boss

Joe, a longtime ETR, says his boss is both difficult to speak to and seriously mistaken about some important corporate “issues.” He believes many ETRs may be in the same position and asks, “Should we tell the boss like it is?” It’s impossible to answer Joe’s particular question without specifics, but I will say this categorically: In most of the situations I’ve seen, people who think their bosses need enlightenment are themselves in need of emergency illumination. It stands to reason.

Bosses generally know the big picture. Employees usually have a more limited perspective. Moreover, bosses are specifically charged with executing the major interests of the business, while employees have more limited duties. Finally, bosses have an edge when it comes to seeing both sides of an issue. Most bosses have been employees and have seen business from the employee’s perspective.

Few employees have been bosses before. So before you tell your supervisor that he’s got his head up his butt, challenge your thinking by discussing your complaints with others — first with other employees and later with friends and disinterested business associates. Don’t just state your gripe. Ask “Do you think I’m seeing this right, or is there another way to look at it?”

By allowing others to give you such feedback, you’ll be able to come to a confident position about the issues that concern you. Then you can make an appointment with your boss to “ask some important questions.” Handle the meeting as an inquiry. Start by asking broad questions about the big issues. “What’s the purpose of such and such?” “Is there any special reason we do it this way?” “What are your [your boss’s] goals and interests?” “What are your concerns?” Most conversations won’t have to go beyond this.

By giving your boss a chance to understand your questions and clarify his views, one of two things will usually happen:

1. The boss will see the error in his ways and decide to change things “on his own.”

2. You’ll come to understand why things are done the way they are and may even find yourself agreeing with him.

If one of these two positive things doesn’t happen “spontaneously,” push on. Continue to ask probing, open-ended, and nonjudgmental questions. Flatter your boss’s ego. Listen attentively to what he says. Take notes. Ask follow-up questions. By “telling off your boss” in this manner, you’ll avoid a potentially embarrassing and even damaging situation — and you’ll get the problem solved in the fastest possible way.

[Ed. Note.  Mark Morgan Ford was the creator of Early To Rise. In 2011, Mark retired from ETR and now writes the Palm Beach Letter. His advice, in our opinion, continues to get better and better with every essay, particularly in the controversial ones we have shared today. We encourage you to read everything you can that has been written by Mark.]