Lesson # 1: Never Let Your Boss Be Taken Off Guard

I actually knew that rule, but I seem to have forgotten it recently. I let my own need to gloat get in the way of protecting my boss from the surprising (to her) and shocking news that her new protege was quitting after only 8 days on the job.

I've been watching the dynamics carefully since I started last year. The boss likes to have someone to mentor, shape and mold. There is an entry level position that attracts ideal candidates - young, impressionable recent college graduates. My boss remembers the days when she first started at this company (the only company she has ever worked for), the men and women who served as her mentors and who she calls her friends today. She wants to be a mentor to someone.

Unfortunately, we have a small department. As well as she mentors someone, there is literally no where to go in this department, so the only way for these young people to grow is to go. And that really frustrates my boss. So, as soon as one leaves, she hires another one, never once stopping to think that maybe, just maybe, even though I'm older and I have experience, I might need a little guidance and mentoring myself. Of course she doesn't see that - because I'm her assistant, and no one ever thinks that support staff can grow into an executive position. Never mind that I came from an executive position - it must be that since I took a support staff role, that is all I aspire to now. But I digress.

So. We hire a new protege. He starts on December 18 and on his very first day, no one takes him out to lunch. This is just wrong, I think, and so I take him out to lunch. At my own expense. And one of the first questions he asks me is "How long do you think you need to stay at a job before you leave?"

It's obvious to me that he isn't going to stay long and I predict he'll be gone in six months. Should I have related that conversation to my boss? What am I to make of it? Is it first day jitters? He has come from a very different work environment, and this company has its own quirks that take some getting used to. The company is closed for Christmas and the day after, and when he shows up for work on December 27 he really wants to talk to the boss. But she is not in, and she doesn't call in either. He's supposed to go to a meeting with her on Friday, December 29, and he tells me that he has pretty much decided that he is going to quit. Should he call the boss?

I tell him that I think he really should have a face-to-face conversation. So he goes to the meeting with her, she introduces him as her new protege and THEN he quits. She is totally and royally pissed, and on the one hand I don't blame her. On the other hand, she had reservations about this guy being overqualified to begin with, and she ignored that gut feeling, so I feel she bears at least part of the blame for the mismatch.

Either way, she was caught off guard and she knows that I knew he was thinking about quitting and I didn't tell her. She hasn't said any of this to me, but her actions tell me so. She is very quick and cool with me, not engaging me in conversation at all even though she had no fewer than three such conversations with others today.

Yes, I'm in the dog house. So there it is, kids, your lesson for today - never let your boss be surprised.