I'm an admin in a really small office. Including my boss, there are only six other people in the office — four of which are full time. Part of my job is accessing my co-workers' emails to send out job descriptions and log responses back. My co-workers have to give me their passwords for me to do this, so they are well aware that I have access to their messages.
A few days ago, I popped into my co-workers' inbox to send a bulk email and I saw that he was exchanging emails with a prostitute. I won't get into the dirty details, but I'm absolutely positive that this is true — he even took a long lunch at the same time as one of their appointments. The fact that he's using his work email when he knew that I, and possibly others, could access it makes me think that on some level he wants to get caught.
I want to report him. This is both morally wrong (he has a wife and two little kids!) and really creepy. The problem is that I want to do it anonymously. My office is so small that I don't think that's possible. What can I do to protect myself? I don't want to be known as the company tattle.
— Not So Anonymous Annabelle
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Dear Not So Anonymous Annabelle,
Unfortunately, since your company is so small and everyone knows that you have access to employee email inboxes, I don't see a feasible way of reporting this anonymously. However, your boss should have the ability to confront your co-worker without bringing your name into things. Keep in mind however, that it is neither you or your boss's responsibility to contact his family about this. In fact, the only business that your company has in the matter is that he's using work email for illegal purposes. Tell your boss what you've noticed. Don't go into details, keep it very professional and simply stated.
If for whatever reason your co-worker learns that it was your complaint and starts to treat you with anything but professionalism, notify your boss immediately. Don't engage in any unpleasant interactions with him. As long as you act with complete decorum then no matter what happens you'll have nothing to worry about and no reason to feel bad. Good luck.