Is It Ever OK To Go Over Your Boss’s Head @CameronMorrissey
Is It Ever OK To Go Over Your Boss’s Head  @CameronMorrissey
Uploaded August 2016 | Updated September 2026, 2 weeks ago
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Transcript:
Hi there, and thanks for joining me today. If you’re passionate about your work, and I trust that you are if you’re tuning into this video, then there are going to be times where you disagree with a course of action or something that’s going on in your operation, and you’re tempted to go over your boss’s head. Today I wanted to discuss when that’s OK and when that’s not OK. The first thing that you want to do in this is you want to take a temperature check of the culture of leadership and whether this is something that’s going to go over, for all practical purposes. The first question to ask is, “Do you know your boss’s boss?” How well do you know them? Do they know your name? Do they know what department you’re from? That sort of thing. That will determine the success of whether this endeavor works at all. If you’re a stranger and you just pop into their office, they are far less likely to listen to what you have to say. So that’s the first thing to do. The second thing is to actually kind of do a temperature check on your boss, and how open they are to criticism, how secure they are in their position, that sort of thing. And the way to do that is to look back on how the conversations have gone when you’ve given them negative feedback, when you’ve disagreed with their decisions. Do they react emotionally, or do they react cerebrally and try to discuss it that way? How they react to you in giving feedback is only going to be magnified if they get feedback from their boss on you. So take a look at that. If they are very secure. If they think things through. Then they might be very open to that way of feedback. So check with your boss to see how they, and check whether you have a relationship with your boss’s boss, before you go forward with any of these discussions. Now, the three areas this comes in most often as far as wanting to go over your boss’s head is when you disagree with the decisions, when you feel like your boss is setting a toxic culture or the wrong culture in the organization, or when there’s legal issues that come into play. The first one where you have an obligation to go over your boss’s head is when there are legal issues, safety issues, hyper-important issues that need to be addressed. In those cases you have a responsibility to the organization to bring it to the attention of HR or you boss’s boss if any of those things are taking place. Now what you want to do when you do that is you want to be specific, you need to bring specifics in regards to safety, harassment, legal issues, that sort of thing. And it’s also very good to bring along another person along with you. That way your boss’s boss or HR knows that it’s not some sort of personal vendetta against your superior, that it is really just something that is for the benefit of the organization. That’s the time where you go over your boss’s head. In the cases of decisions and culture, it’s almost never a good idea to go over your boss’s head. The reason is it generally reflects poorly on you. The ability to convey your thoughts and convince people of your position is a leadership trait. If you go over your boss’s head and start discussing how you haven’t been able to get through to your boss on this, this reflects just as poorly on you and your negotiating abilities and your ability to communicate and bring consensus to everybody. In regards to culture, your boss’s boss is just as likely to have set the culture tone as your boss has. So in this case you might criticizing the very person who came up with the culture that you disagree with. But it really should be, if you decide to go over your boss’s head, you know I applaud the courage on this one, you want to lead with solutions. You don’t want to lead with the problem, you want to give the solution as much as possible. And utilize this as an exercise as much as possible in getting your point across and communicating well. Those are the times where if you can go over your boss’s head you can demonstrate the leadership qualities and hopefully cancel out the negative effects of it. But it’s a very tough thing to go over your boss’s head, I don’t recommend it in almost any instance, but there are times where it’s appropriate and necessary for the organization. I hope I was able to help you out a little bit with that tough question today. Thanks so much.
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Is It Ever OK To Go Over Your Boss’s Head

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