This scenario plays itself daily in American workplaces, yet few career dilemmas are more problematic. Our impulses often would have us go over the boss' head, but such a course is fraught with heavy risks ranging from being permanently cut out of the loop by supervisors to outright termination in extreme cases.
Experts warn that even though the U.S. workplace touts its "participatory culture," many managers still view challenging the boss's decision as disloyal, even outright insubordination. Appearances can also be deceptive even if you do seem to survive your insurrection unscathed; you could still face a reputation as a troublemaker or malcontent.
Still, if you're determined to make your case, you should ask yourself some questions first, advises Virginia Rehberg, a Boston-based career consultant and the "career doctor" on WBZ-TV. For example, is the case you're trying to make with upper management really worth the potential fallout, or are you perhaps indulging your own ego--or, even worse, exacting revenge for some earlier slights at the hands of your supervisor?
In other words, before you take this very risky step, you must be certain that the cause is justifiable. Once you make your move, it's all but impossible to reverse course.
Rehberg advises people to seek out their bosses first before going around them. "You have to give that a try first. Otherwise, you won't have much credibility with upper management."
How should you actually approach your supervisor's boss? "The best way is to 'accidentally' bump into them, by the water cooler or in the lunchroom," says Rehberg. "That way you can make it casual and not look like a formally planned thing."
What if you're issues are more broad-based, such as dealing with an incompetent or an abusive manager? "Then you need to be prepared to fully document your allegations and have it all well organized," Rehberg says. "Even then, it's a tough assignment."
Of course, there are situations where your course is more clear cut. For example, if your boss is skimming the till or doing something clearly unethical, you are obligated to inform senior management. Remember: workers with top performance records have the best chances for successfully bypassing supervisors.
On a pragmatic note, workers who do circumvent their bosses should have some kind of "escape hatch" in case they need to leave the company. Before you make your move, start checking out leads both inside and outside of your current firm. If you do have options, it will make your position stronger.
