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Advice / Succeeding at Work / Work Relationships

Is it Ever OK to Go Over Your Boss' Head?

While some employers like to boast that they’re “flat” organizations, the reality is, all of us report to someone at the end of the day. If you’re lucky, you’ll have a boss that knows what he or she’s doing and will become a great mentor and ally for you.

But, bosses are people, too, and sometimes they make a mistake or (gasp!) don’t have all the answers. What then? What if you can see a disaster coming from a mile away, and your boss doesn’t see it? Or what if your manager is doing something you know isn’t right? Are you supposed to just sit idly by while carnage ensues?

The answer, as you may have guessed, is not a simple yes or no.

Whether your boss is a rock star or ridiculously under-qualified, this person is still your boss, and someone put him or her in that place for a reason. Which, in short, means you need to respect that as much as possible. That said, there are a few serious situations where going over your boss’ head is definitely OK.

If you’re considering a flanking maneuver on your boss, check out these dos and don’ts before making your move.

Don’t: When You Just Don’t Like the Job

Hating your job is a drag—trust me, I feel your pain. But, even if you think your boss is the devil incarnate, that’s not necessarily his or her fault. For example, if your manager continues to dole out seemingly tedious assignments even though you’ve expressed your desire for more advanced responsibilities, chances are, there's a reason. In fact, he or she probably loathes giving out the assignments as much as you hate following them.

The first time I experienced this was with an employee who constantly complained about the tasks I assigned to her. No matter how hard I tried to find ways to mix things up and re-engage with her, she had already decided she hated her job, and nothing I did was changing her mind. Eventually, she decided her dissatisfaction with the job was a direct result of my management style, and she expressed her frustration directly to my boss.

When my boss pulled me aside to fill me in, I was devastated. While he said he knew I was trying my best and reiterated his support for my approach, I couldn’t help but take it personally, and it was a huge blow to my confidence. For several weeks after, I constantly questioned my methods—not to mention that employee’s sense of loyalty—which didn’t help the team, or me, improve performance.

If you ever find yourself tempted to tattle on your boss, first ask yourself it it’s really your boss that’s the issue, or if it could just be the fact that you don’t like the job. If it’s the latter, try to come up with a list of ways the job could be more satisfying—and taking that up with your boss directly, instead. And, if you can’t come up with a single thing for that list? Maybe it’s time to start looking for a new job.

Do: When Your Boss is Breaking the Rules—Big Time 

You know that saying, made famous by the Department of Homeland Security, “If you see something, say something?” Well, the same goes for your work environment. Although we may not all receive the same level of corporate governance training, it goes without saying that we’re all on the hook to some degree if something starts going south in the home office.

While I’ve never had the unfortunate distinction of being involved in a corporate scandal or investigation, I’m pretty sure there are a few former Enron employees who wonder if disaster could’ve been averted—at least to some degree—if they’d disobeyed the boss’ orders and reported what was going on.

That said, going over your boss’ head, especially when it’s under delicate circumstances, is a tricky maneuver. Simply running to the CEO’s office and blurting out that you saw your manager shredding documents after hours would not be wise. Instead, gather as many facts as you can, including dates, names and any specific information related to the situation. When you’re sure something shady is going on, schedule a meeting with someone senior to your boss, and discuss what you’ve found. Be sure to express your concern for both your boss and the company when sharing your story. It’s important that whomever you speak with understands you’re looking out for the company—not simply trying to tattle on your boss.

Don’t: When You’re Trying to Get Ahead

Probably the most tempting time to flank your boss is when you see an opportunity to surpass him or her. But trust me—this is a huge mistake.

Fortunately, I’ve never done this myself, and I haven’t had it done to me (at least, as far as I’m aware), but I have seen it happen to colleagues, and it’s not pretty. Here’s how it plays out: Employee smells weakness in boss. Employee starts to position herself for advancement by subtly discrediting boss and promoting her own ideas. Someone with a “C” in her title notices. Employee thinks she’s on the fast track, only to find out the C-level colleague was just scoping her out and now questions her loyalty and ability to recognize leadership. Employee is now branded as an opportunist, rather than ambitious, and is passed up for the next big promotion in the group.

The lesson? While opportunities will definitely present themselves, remember that managers of all levels look for loyalty, collaboration, and general ability to be a team player when promoting their employees. What’s more, your actions matter, and how you respond to your boss is a direct reflection on your ability to tow the corporate line. While that may seem a bit dictatorial, think about this: If you had your own business, wouldn’t you want to know with as much certainty as possible that your employees would stick behind you, no matter what?

Do: When You Encounter Harassment or a Hostile Work Environment

While it may seem obvious that one should immediately report instances of harassment or a hostile work environment, actually going through with it is complicated, to put it mildly—especially if it’s your boss that’s the source of the issue.

I’ve experienced harassment with nearly every job I’ve ever had over the past 15 years, ranging from sexist comments in the elevator to physical harassment and everything in between. And you know what I did about it for most of those years? Not a thing. It’s probably one of my biggest regrets in my entire career. Why? Well, aside from the obvious, I was inadvertently setting up an environment that turned a blind eye to situations that were definitely not OK.

It wasn’t until one of my employees finally came to me to reveal that she had been harassed by my boss that I realized I had to do something. Then came another. Then, of course, there was my story, too. I realized at that point I had let not only myself, but my entire team, down by allowing this behavior to continue. So, I went over my boss’ head.

I wish I could say it was easy, but it wasn’t. Telling your boss’ boss his or her second in command isn’t cutting it as a manager is a difficult conversation. Telling your boss’ boss he’s been sexually harassing an entire group of employees felt impossible. But, the courage my employees showed in telling me their stories proved to me it could be done, and within a week, the issue had begun to be addressed.

If you’re experiencing—or witness—harassment of any kind, or a hostile work environment, know first and foremost that it is absolutely not acceptable, and it needs to be stopped, pronto. Chances are, you probably aren’t the only one who’s noticed, and given how difficult it is to broach this subject, it’s likely no one has ever reported it. Which means that’s your cue to drum up some courage and take one for the team.

Just like the situation where a boss is doing something against company policy or illegal, though, do get as much detail as you can about what’s happening, and make sure you bring your notes to the meeting. It’ll probably be an emotional experience, so be prepared to have all your senses firing on all four cylinders. That’s completely normal, and in no way should it deter you from telling your story.

We all deserve to work in safe, productive, and respectful environments. While we often look to our managers to assure that’s happening, occasionally, we need to shine a light on the situation ourselves.

I can guarantee there will be dozens, if not hundreds, of times you’ll feel the urge to go over your boss’ head. But, by thinking through each situation first and determining the best course of action, you’ll help establish yourself as a committed member of the team and position yourself as a future leader who knows how to navigate the maze of company hierarchy with grace and respect.

Photo of woman talking to boss courtesy of Shutterstock.