Dear Jewish Fairy Godmother:
I work with a woman I have very mixed feelings about professionally
and personally. She’s the company accountant and runs all the
financial aspect of the firm where I am the manager. We don’t agree
on anything except whom to hire and the weather, but I have never
before had reason to doubt her honesty. She supports a deadbeat
husband and as far as I know (she’s pretty open about her family
history) there’s no sugar-daddy uncle in the picture. I just found out
that she bought a new house, a new horse, and three months ago, a
new Lexus. She doesn’t make any more than I do, and I drive a four-
year-old car and support one person, not four. We’ve never been
audited. Is it my job to alert anyone higher on the food chain or should
I just let this unfold as it does? Obvious as it may sound, I need my
job.
Suspicious

 
Dear Suspicious:
You’ve got me convinced that she’s living way beyond her means. If I
owned the company, I’d probably want to have another set of eyes on
the books. The question is, do you want to get the praise for shining
the light on her if you are right, or the booby prize for false
accusations if you are wrong? If you’re willing to carry the weight
either way, ask you boss for a private meeting and say I have some
concerns. You can ask for confidentiality but there is absolutely no
assurance that it will be maintained, no matter what you are told at
the time.

 
I’d start by asking her, in a pseudo-friendly coffee cooler kind of way,
Wow, did you come into some money? I’m on careful maintenance
given the economy. Then the hard part shut up and listen. I suspect
there’s very little she can say other, including that she had a winning
lottery ticket, that would truly allay your suspicions. So you are back
to Plan A, talking to your boss, or the always unreliable but
superficially safer Plan B, the anonymous email. Note that if you’ve
already probed you’ll still get tagged as the likely source. Also,
anonymous is increasingly harder to do in this technological age. But                          you’ve certainly got me curious if she’s printing money or has a
legitimate explanation.