Dear Jewish Fairy Godmother:

My former assistant is one of the last people standing in the branch
office I used to manage. The handwriting is on the wall for the
company closing it down but she’s under the wing of our supervisor,
the original company founder. She’s 55 and does not have very strong
computer skills, so she’s rightly concerned about being thrust into the
job market. She’s been well paid for doing many personal chores for
him, as well as corporate work that’s drying up. The new owners are
letting him graze in pre-retirement pastures, but that’s won’t help her
when they shut the place down. She asked me to read her resume and
to write a reference so she could apply for a job another colleague told
her about. She’s almost certainly going to have problems finding any
position as good as what she has now, and she is a great person, so I
gave her a strong letter. Now the big boss, who feels completely
dependent upon her staying, asked me if I was helping her look for
work. My sympathy is with her, but he has been very generous to me
over time, and still comes to me to help him out. What should I say?

Helping Both Sides

 
Dear Helping:

You should give a qualified Yes, otherwise known as a white lie. Say
she asked you for a letter of reference for a specific job that someone
told her about. Omit mentioning the resume help or any coaching and
advice you may have offered.

 
Tell him how bad the job market is to women over fifty who lack
strong computer or technical skills. If he’s been a boss for a long time
he’s probably very out of touch with the realities of looking for work,
but very used to having people at his beck and call. Assure him that
unless she gets very lucky, her search is likely to be long. He may
even have to go to bat for her with the corporate powers if he wants to
keep her longer than they do. Finally, reassure him that she has never
spoken in any way except with personal loyalty towards him and
regret about the changes. Finally, tell him that if she were to find
something, you and she would help him find a good replacement. End
with, When have we ever let you down?