Dear Jewish Fairy Godmother:

For a very long time I was the executive assistant to the boss of a
department in my organization. In that role I learned a lot about
various co-workers and had to listen to my boss dissect their flaws,
often in the least flattering and least compassionate ways. Now my job
has changed. I am working with many of the same people as peers, as
people I now supervise, and in one case, as my new boss. The old
boss still tries to corner me in his office with his snarky and mean-
spirited comments, like he needs an audience to validate his
unkindness. In addition to being mean, he’s long-winded, and I don’t
want my new boss to think I am ratting him out to the old one. I really
like the new guy who does not do the same. How can I unplug from
the old boss?

Hear No Evil

 
Dear Hear No Evil:

When roles change in organizations there is always some re-calibration
that is required. Mature adults handle this kind of process better than
people with a middle-school need to be unkind to others. You have the
unenviable job of educating your old boss Fortunately you have a new
boss as an umbrella, should you need one.

 
Next time Old Boss tried to corner you, stay in a public place for the
discussion. When he starts on one of his diatribes, say very simply: My
job and my role has changed here. I no longer want to hear you talk
about people. I’ll talk to them directly. Please don’t ask me to listen
again. Then go to your new boss and, without revealing what might
have been said about him in the past, explain the old behavioral
patterns. Tell him you’re hoping they’ll stop on their own. But if not,
you may ask him to say something because you so very much value
working for him that you don’t want to give any impression that you
are not a good team player for him. It may come of syrupy, but if you
are doing a good job and don’t linger too long at the proverbial water
cooler with others, he’ll be able to see you for who you are, not how
your old boss treated you.