Stanley Bing

Ask Bing: My boss is hiding

Fortune's Stanley Bing tells readers when to do the most scary thing in business: Tell the crazy person the truth.

By Stanley Bing

Q: My boss wants to be kept abreast of what is going on, but he does not want to return phone calls or answer e-mails. What's the best way to communicate with someone like this?

A: Yell in his face? No, but seriously. Your boss wants to know some things and not others. This may, in fact, be a good idea. Perhaps he's not set up to handle upsetting things, and needs to keep his concentration.

Perhaps this is the kind of boss that needs a Food Taster. Tell him you understand that and apply for the position. After that, everything that goes onto his plate must be sampled by you, chewed thoroughly, monitored for signs of poison. Only then should it be passed along to him. Now, obviously, there will be some things loaded with venom that he absolutely positively needs to see. These must be broken up into teeny-weeny bits and fed to him very, very slowly so that he does not either choke on them or spit them up all over you.

If, on the other hand, you're talking about a guy who keeps his door closed, never answers his phone and doesn't reply to e-mail, you're dealing with a certain kind of demented individual. All you can do is wait for his style to cause trouble for him - as indeed it most certainly will. When that happens, and he wheels on you with a "Why didn't you keep me informed?!" you need to do that most scary thing in business: tell the crazy person the truth. Good luck.

Is Bing's advice on track? Tell him what you think.

Q: My co-worker has been out sick - a lot. I'm pretty sure she's used up more sick days than we get at our office. Meanwhile, I have to stay late to do her work. Our boss seems oblivious to the absenteeism - should I point it out?

A: Yes. Screw it. Life's too short to cover up for lazy people. On the other hand, in case the person has something really sad and serious, you may want to ask her what's up. You don't want to cause more trouble for somebody who needs a little help because she's ailing.

My guess, from the tone of your question, is that this is not the case, that we're talking about a person who has carved out that niche for herself where people expect very little of her, and are satisfied with the solution to the problem: You. That's bulls**t. Speak up.

Q: I'm very attracted to one of my co-workers, and she has flirted with me at several after-work drinks. The problem is, she's married and much younger than I am. But I believe she's interested in me too. Should I send her flowers?

A: Oh, yes. That's a good idea. I'm sure nothing but happiness will come from it. But seriously. Unless you're a total risk freak, it's probably not the greatest idea in the world. If she's much younger than you are, it's probable that she's junior to you? That's a lawsuit waiting to happen. If she's a total peer and there are no power issues, I supposed you could taste that sweetest of all forbidden fruit - sex that you should under no circumstances engage in for a variety of personal and professional reasons. But unless you think this is the love of your life, it's going to end, people are going to be hurt, and the office will become a hotbed of recrimination, guilt, shame and paranoia. More than usual, even.

If, finally, you're just a romantic, immoral, stupendous fool, and nothing can dissuade you, try the little room at the end of the hall behind the copying machines. Nobody ever goes in there.

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