Hello, I have noticed my boss breaking company policy. Should I report him? I am afraid that he will get caught and we will all be implicated or he may retaliate against me.
There is no simple way to bring this breach of policy to the attention of your boss, knowing that most whistle blowers get hurt one way or the other even if they are innocent. Subsequently, they have difficulty being trusted and their presence is threatening to those around them. They also have a difficult time finding employment since most of them have already lost their job.
One possible way to accomplish this objective without raising any suspicions from your boss is to bring a real or theoretical situation to your boss in which company policy must be followed, request clarification of this policy from your boss in a casual conversation. As the boss explains this policy to you it will make him aware that someone knows and is aware of this policy which might induce a course of self-correction without anyone ever knowing what has been going on in the company. You intention is not to hurt or expose him/her to possible harm but to make the boss aware of his/her ethical obligations and initiate a self-correction.