Recently, our company underwent a major reorganization. I now report to a supervisor who I think isn’t up to the challenge, and I feel compelled to talk with his boss. Is it ever OK to go over the boss’ head?
—Need Advice Before Crossing the Chain of Command

Going over the boss’ head is a tough career call. It’s fraught with risks, and, in particular, it brings up such sticky issues as loyalty and ethics. Opinions vary on this touchy subject. Some business cultures encourage skip-level communications; in others, bypassing the boss simply goes against the grain. And, should you decide to go over the boss’ head, you have no assurance that your expressed concerns won’t be shared word for word with your supervisor.

That said, how would you feel if someone under you went over your head? My sense is that it would not only make you angry, but it also would make you feel betrayed. More than likely, you’d find it difficult at best to trust or work with that person moving forward. Certainly, if your boss is doing something illegal or unethical, there’s an obligation to speak up. But in this case, the first person you should talk with is your boss. Maybe you’re not assessing the situation correctly, and there’s a good explanation for your supervisor’s managerial direction. If you feel his explanation is inadequate and are compelled to inquire at a higher level, you might say that although you respect his judgment, you’d like permission to discuss this with higher-ups. He might surprise you, but if he says no, I’d drop it there (and hope your résumé is in order).

Some other thoughts: If you have a good relationship with the boss’ boss and know that he/she values your opinion, this might provide an avenue for a productive conversation. Or, if your work group shares your opinion about the boss, the entire team might want to schedule a meeting with the boss’ boss. There’s power in numbers. The boss’ boss may be more likely to listen to an entire staff’s opinion versus your individual complaint, especially if he/she is unaware of the situation. (Regardless, it is important to get to know the boss’ boss. Make sure he/she knows your name and chat when the opportunity presents itself to develop a long-term, mutually beneficial relationship—you never know when you will need a valuable ally). Finally, if your HR department welcomes this kind of input, it might provide another alternative. If not, you’re wasting your breath and probably your future job security.

Bottom line: Studies have shown most companies view going over the boss’ head as an act of insubordination. Once you get this label, you’re always at risk because nobody trusts you. In my humble opinion, transferring or even quitting may be more prudent than insurrection.

If you have a question for Joan, send it to business@townandstyle.com. Joan Lee Berkman is a marketing and public relations consultant.