How to Successfully ‘Boss’ your Boss

The Delicate Art of “Managing Up”

By Robert J. Flower

Some might call it being manipulative; others would argue it’s an essential workplace skill. It’s managing up — the art of gaining the buy-in of your boss to achieve your own ends. Managing up is a multi-step process, and it all begins with communication, says Dr. Robert J. Flower, an Entelechist and the author of numerous books on Potential and finding purpose.

“You may be consumed with a change you want to make, whether it’s a bold new business idea, a pay raise or just a little more courtesy around the office,” says Dr. Flower. “When something feels really important, it can be very hard to look past it and see the larger picture. Training yourself to open your mind to that takes practice, but it will improve the odds of getting what you want.”

Dr. Flower offers these tips to determine the most effective methods for communicating your wishes and getting results.

Imagine the roles are reversed. A simple trick for getting a better perspective on how a conversation will go is to imagine yourself on the receiving end of your proposal. Would you listen to you? 
 “What you have to remember is that this thing you’re obsessing over may not even be on the manager’s radar, or may be perceived in an entirely different way,” Dr. Flower says. “Your boss has his or her own set of priorities. Figure out what those are, and how your request will be received in that context.”

Do your homework. Do your personal objectives appear to serve to advance the goals of your boss? If not, it’s time to do some research and think creatively.

“Maybe you have the bright idea that you want to telecommute twice a week. On its surface, that’s not necessarily something that will look appealing to your boss,” Dr. Flower says. “However, if eliminating the travel time will free you up for one or two extra hours of productivity on those days, it will be much easier for a manager to see the value of that.”

Connect the dots. Be prepared to spell out the benefits of your idea in crystal clear terms. Use data to make your case, advises Dr. Flower.

“If you want to telecommute, find a study that shows how telecommuting improves productivity,” he says. “And be detailed about what, precisely, you could accomplish during those extra hours that you’re not available to accomplish when you’re commuting.”

Tailor the message to the audience and situation. Bosses are busy, so if you want them to listen, you need to be considerate of their time and attention, says Dr. Flower. “For something like our telecommuting example, you would probably want to schedule a meeting time in advance, get all of your facts in order beforehand and simplify any visual aids as much as possible for a streamlined pitch,” he says.

But there are times when an overt request isn’t necessary, or even advisable, Dr. Flower says. “Let’s say you’d like to see the office run a little differently. If your manager has a sensitive ego and might take your proposal as a criticism, I might advise you to subtly go ahead and start making the change you seek without asking. Then praise the boss for the change after the fact, as though it was all his or her idea.”

Managing up can be a little sly, Dr. Flower acknowledges, but in the end, everyone is happier.

Dr. Robert Flower founded The Gilchrist Institute for the Achievement Sciences in 1982, a nonprofit Human Potential Research and Development think tank located in Bronxville, NY.

Robert J. Flower, Ph.D., Director, The Gilchrist Institute for the Achievement Sciences | Bronxville, NY (914) 779.6299 Email:

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