-- D. G., Trenton, N.J.
A: Congratulations on making it into the management ranks. And now, for the bad news: It's likely that you will have to deal with lots more headaches like this one.
There's no simple answer to handling the difficult employee -- or the boss who has difficulty letting you manage this person. That's mainly because it's usually unclear why your boss is getting in your way, says Tom Welch, president of career-coaching service Career Dimensions and the author of Work Happy, Live Healthy. Perhaps your boss thinks the employee is right, for whatever reason. Maybe your supervisor doesn't think you have what it takes to manage somebody. Or perhaps your boss simply doesn't have a clue that his or her actions are undermining you.
Whatever the case, it's high time you had a little coffee talk with your boss, our experts say. "Until the boss and the manager get together and figure out what the differences of opinion are, the manager isn't going to be able to work it out," says Welch, who's based in Stuart, Fla.
To get the boss talking, it's best to go in with a specific example or two of problems you have with the employee. For instance, if you've been telling the person to show up at work before lunchtime, but your boss tells the underling it's O.K. to come in late, point out nicely that "this is undermining me," says Margaretta Noonan, senior vice-president for global human resources at New York's TMP Worldwide, a large recruiter. "The key is to keep it professional and fact-oriented," Noonan adds. "It helps the boss respond in the same way." So, don't stomp into your supervisor's office shouting: "You're making my life miserable," even if that's true.
GET CLARIFICATION. The response you get will say a lot about your boss's quality. "A good leader will be wide open to it," says Welch. "A poor leader won't be -- and maybe you don't want to be working for that person anyhow." Use the time with your boss to clarify exactly what's expected of you as a manager, says executive coach Paul Bernard, principal of Paul Bernard & Associates in New York.
If you get the chance, specifically ask your boss what he or she sees as your major responsibilities and how much time you should spend on each one. If your boss says only 5% of your effort should be consumed with overseeing the problem employee or other subordinates, maybe you don't need to sweat it as much, Bernard says. The dirty little secret, he adds, is that "you also have to learn to manage your boss."
Getting feedback you can use to solve the problem will of course be your main goal, our experts say. Be upfront with your boss about assessing your abilities and needs. Bernard suggests asking something like: "Where do you think my skill level is as a manager, and what resources are there to get some more training or coaching?" If all goes reasonably well, you may come around to your boss's way of thinking, your boss may come around to your way of thinking, or you may meet in the middle, Welch says. "If you're going to lead the troops, you can't have diverging views," he adds.
ASK AN ALLY. Two other outcomes are possible. One may be that you're truly out of touch with your abilities to manage, although someone conscientious enough to write in with this problem is probably doing something right. The other is that your boss will remain in denial -- he or she won't think that a problem exists. If either or both is the case, it could help to approach a trusted confidant -- an ally at the office who will keep the situation confidential, a former B-school professor, or someone else outside the company -- for advice on dealing with this challenge.
If such people are honest, they'll tell you if you have a legitimate gripe or not. Sometimes, the emotions or politics in an organization can cloud your thinking and blow an issue out of proportion. Alternatively, this person could also tell you that your supervisor stinks and is making your job a living nightmare. In that case, you'll still have to make peace with your boss. Or if the situation gets really bad, you may have to escalate the discussion to your supervisor's boss. If your sanity or health is at stake, you may even want to find a way out of your job -- or leave the company, experts say.
The problem with taking the problem upstairs, of course, is that you risk making a tense situation worse. It's best that you get only your boss's superior involved as a last resort, our experts agree. "There are always risks when you go over your boss's head," says Noonan. "Lots of bosses, myself included, don't like it when you rat on them."
With the job market the way it is right now, it's probably unwise to take a lot of risks at the office. Given the choice, be a peacemaker, not a warrior. By Eric Wahlgren in New York