When You Know Your Boss's Personal Business
by Therese Droste
Monster Contributing Writer
When You Know Your Boss's Personal Business

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    STICKY SITUATION: Last week, my boss was tied up and asked me to take three of his best clients (who are also his old friends) out to lunch. They went through a lot of wine during the meal -- I had a glass myself -- and regaled me with sordid stories about my boss. One of the execs started spilling stories about lap dances my boss ordered at a strip club during a Las Vegas convention. The stories went around the table until my most inebriated lunch mate started talking about how my boss has been cheating on his wife for years -- with several women.

    I've worked with my boss for many years, I'm close to his wife and family, and I've always respected him. But now I find it difficult to hide my disgust toward him. He asked me yesterday if anything was troubling me. I almost spit out my coffee, but I managed to tell him everything was fine. I don't know if I can work for this man anymore. I also feel like I'm lying to his wife by not telling her about his affairs. What should I do?

    WHAT THE EXPERT SAYS: It sounds like your conscience is bugging you about his transgressions. You're truly going above and beyond the call of an assistant's duties to take on what should be the boss's guilty feelings. Then again, it doesn't sound like he has any problems breaking unwritten social rules for good behavior. Unfortunately, you discovered that your beloved boss is human, but not the type you can stomach on a daily basis.

    Take a step back to view the situation. Take your personal feelings toward your boss and his family out of the picture. Realize that this is business, and many successful and powerful people may look good in public but then roll around in the mud in private. While many assistants can separate their personal feelings about their managers from the business at hand, many others find it impossible. It sounds like you fall in the latter category.

    You need to ask yourself if it's truly important for you to work for someone you admire and respect, or if you could work for anyone as long as you are meeting your career goals and the job is interesting. If it's the former, you need to move on. You don't necessarily have to move out of the company; you could request a transfer to another department.

    You'll also have to follow your conscience about whether or not to tell your boss the real reason you're moving on if you do leave your job. Frankly, I don't see anything to gain in spilling the beans unless you truly view him as a friend and are so disgusted you can't help yourself. Still, will anything be gained? How do you know his wife is not already aware of his infidelities? Would it make her feel better that you and his cronies know, too? Indeed, it's possible your newfound knowledge could actually turn against you in the form of a bad reference or broken friendship. Simply put, your boss could view the information you now know as a threat to both his job and family, and he could find ways to work against you.

    The next six to eight weeks will be crucial for you, as the information sinks in. You'll either find a way to deal with it and continue working professionally in your job, or you'll feel the need to move on. If you find that every time you look at your boss the word "pig" pops into your head, it could distract from the business at hand. Either way, you'll have to follow your own conscience and best judgment. Whatever you do, don't gossip with your colleagues about what you've heard. At its worst, it can destroy careers. Do you want that on your conscience?