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When it comes down to it, there are two reasons that people go over their boss's head - to further their own position or because of a problem or incompetence affecting business. Of the two reasons, the former is the most common and the most likely to come back and bite you someday because its only motivation is self-interest.

In the second case, where business and other employees are affected by a situation of incompetence, gross negligence, or dishonesty, going over your bosses head can be warranted. When deciding if you should go through with it, the first thing to ask yourself is if your motives really are good and if there is a valid reason. If so, the next thing to determine is who to go to. There are often several people above your boss in an organization, and you should pick someone that you know to be fair and reasonable. If you have reason to believe that people above your boss are aware of the situation and are doing nothing about it, they are not the people to go to. The other thing that is important is that the person you go to is decisive. Situations like this needed to be handled diligently and as expediently as possible for all people concerned.

Once you have gone above your boss, you need to be aware of their reaction. Most of the time, your boss will find out you went above them, because upper management will attempt to find a solution to the situation. If you boss appears angry with you and things seem volatile, you should interact with your boss as little as possible for a few days and allow the situation to settle a bit. If things get out of hand, go back to the person you originally talked to so that they are aware of the situation. Not matter how angry your boss may be, a basic level of professionalism should still be maintained.

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