While generally considered in bad taste, sometimes going over a superior’s head is necessary.

We see it every day at the American workplace. An employee at a lower level goes beyond their immediate manager in an attempt to have a suggestion taken into consideration, a document approved, a request granted, or other question resolved. In rare cases, the act is innocent, and the employee truly didn’t put much thought into taking an idea to an upper-level manager. Much more commonly, though, going over a boss’s head is a desperate, conscientious move to gain an approval that otherwise would surely have been stricken down, or perhaps was already stricken down by an immediate manager.

Going over someone’s head is also oftentimes a move made by a lower level employee to simply look better than their immediate supervisor, thereby making that person look bad or unfit for their role. The lower-level employee may even be gunning for their immediate supervisor’s job.

While the move frequently works and the employee is granted the permissions sought, they will have to deal with an angry supervisor who feels their authority is being disrespected. It has cost people jobs, created office friction and hostility, derails a team from achieving their goals, and creates lifelong enemies, yet it happens every day.

How do you decide if you should go over your boss’s head?

It all comes down to how badly you want something, really. Consider these scenarios when deciding if this risky move is right for you.

• How innocent is this? Sometimes we just go to the next-in-command without any thought. “Hmm, Mr. Rodgers didn’t like this plan, but maybe Mr. Cousins will!” Unless your honest response to being scolded by your boss is something along the lines of “Oh, no, I didn’t mean to go over your head! I’m so sorry!” then maybe you should think twice.
• How desperate are you? If the matter at hand is life-or-death, then yes, go for it. If Rod’s manager blew off his request to attend a trade show and it could mean the difference between closing a major deal or not, then it’s probably worth it for him to plead his case to the next-in-command.
• How angry are you? If your manager upset you with their short, stern response to a question, proposal, or assignment, maybe you feel like it’s worth it to risk their wrath and go over their head. If Bob worked for two weeks on a presentation and his boss simply said “Total do-over!” maybe he should run it up the ladder.
• How “big picture” is the matter at hand? If you’re mopey about being told “no” on a design you made, but have no real intention of making a bigger play for your boss’s job, a big raise, or more input in the company, then perhaps take a step back and reconsider. Going over a boss’s head should probably be reserved for making a bigger play career-wise rather than a single project.
• How under-qualified is your boss? If the whole idea of going over your boss’s head is to show his/her boss how dumb they are, then maybe going over their head is a good idea. If Jennie’s boss is completely incompetent, how will Jenny ever get ahead? “I showed the TS-55 layouts to Mr. Bradbury, and he said the H-rod would never fit below the quick-grind shaft. But I accounted for the slag of the north cut holes, and it does fit! See?”
• How badly do you want your boss’s job? Likewise, if you truly feel you’d be better at your boss’s job than they are, maybe it’s time to go over their head and see. Sometimes, upper management will see these things for themselves over time, but other times it just has to be set in front of them. If Darryl’s boss is a total slacker, maybe go over his head. “Mr. Botts, I don’t mean to throw Chip under the bus, but he blew off early for the day to play golf and I need someone to sign off on these blueprints I designed all by myself.”
• How sure are you your boss’s boss is going to be cool with this? If all else checks out, you should consider how close your boss and his/her boss are. Is Mrs. Tittlesworth going to be cool with you going directly to her when it’s understood you report to Mrs. Bell? If you think their response might be a redirect back to your boss, now you look like a devious employee trying to create chaos, actually hurting you in the long run.

The bottom line is that no boss wants their subordinates going directly to their superiors. Simply put, when all is said and done, someone is going to wind up looking bad. A typical response to a boss finding out that you went over their head, especially after their decision had already been made, is certain to be anger, or in some instances maybe hurt feelings. Unless you feel that going over the boss’s head is a long-term, big-picture win for you career-wise, you might want to take a step back and try reasoning with your own boss again.

My Hot Take

In my 12.5 years of professional marketing work, I can’t specifically recall a time where I egregiously went over a boss’s head. No doubt these types of things happened more often a decade ago at my first job, when I could have seen myself taking a rejected project to the next-in-line and hoping to win their approval.