What lf My Boss Tries to Block My Promotion?

Last Updated Jun 4, 2009 2:59 PM EDT

Dear Stanley,
I've been an assistant for a long time, working for a very nice woman who has become quite dependent on me. An associate position, which is the first step on the rung to management, has just opened up in my department. I would like to put in for the position. I've earned it. I could do it well. But I'm afraid that my boss has become so used to the things I do for her that she can't function without me and won't let me get promoted. I also worry that she'll see me as being disloyal for wanting to leave my support position. What should I do?
Born to Fly

Dear Flexible Flyer,

Go for it, by all means. You were hired to do a job. You've done it well, and now you're ready for a promotion. Your ability to pitch for that new post and get it will determine whether you have what it takes to be a bigger fish in the pond in which you're swimming. A person's reach, as it is said, should exceed their grasp. In this case, you're not even being excessive. You're being reasonable.

And that's the rub. Because bosses aren't reasonable. They may try to be. They may think they are. But the cold heart of Authority is always defining the universe by one simple question: "What does it mean for ME?" I'm not saying your boss is evil in any way. She simply will define your move as something that is good for you and bad for her. This may not mean she will oppose you -- but she will have to fight a pitched battle with her own executive nature not to do so ... every day. Just when she feels like her decent side may have the upper hand, she will need you for something and think to herself, "I won't have him/her to do this for me if he/she gets the new job. What will my life be like then?" And she will be filled with self-pity and resentment.

But you must push on. Because somewhere in the heart of every boss, there is a little person who is actually not completely demented. All right, not every boss, but most. And in that tiny, walnut-sized enclosure, there is a realization that every person -- even a person who is not them -- has a right to some advancement and happiness. In fact, the ambitious person you work for will, in the end, respect another ambitious person more than one that has no thirst for advancement.

Play the situation carefully and aggressively. Go to the boss. Tell her you want the job. Lay out your qualifications. Make sure that you say, "I realize this may be a pain in the butt for you, but I feel like you have trained me so well that I just might do a really good job here." This will put the boss on notice that she has to be a "good guy" and hopefully lead her to say, "Yeah, it's annoying to lose you, but I'm not going to stand in your way." Only the most diseased executive ego would admit to standing in somebody's way (even if they really want to). At that point, she's on the record. She's going to support your move (publicly) and refrain from being a selfish monster (except at times privately).

Now move fast and hard to get what you want. The ability to do that is what will produce whatever success you have in the years to come.