Dear Jewish Fairy Godmother:

I work with someone with whom there is mutual and active dislike. I
am her only supervisor and report to a boss of my own who thinks she
only needs better direction and instruction. He is unwilling to mentor
me in how to provide it or take his own time to give it. Sadie is a
single mom (something she tells us regularly) who tries to ingratiate
herself with everyone (except me). Ironically this has backfired and
she’s managed to annoy most of the staff with her prima donna
attitudes. I’m responsible for training her and getting productive work
out of her. I have tried being her friend, being stern, and being
professional, but nothing seems to dent her pseudo-sunny personality
and haphazard performance. She’s been here a very long three
months. How much more time do we owe her to see if she will work
out?

Suffering Supervisor

 
Dear Suffering:

It’s always hard to be caught between bad help and a hard boss.
Assuming you want to keep your own job, you’ll have to tread carefully
and document your footsteps. Most of all, don’t take it in emotionally
so much that you lose your own self-esteem or act in ways that might
reflect badly on you. Give all your instructions in writing, finding a
balance between micro-management and careful explanations. Cc your
supervisor if the task is particularly important to his deadlines, so it’s
clear that you see the big picture and gave your staff enough lead time
to meet the needs of the project.

 
As for how long you’ll suffer before a change, immediately do a three-
month evaluation. Be explicit about both her flaws and performance
expectations for the next month. Repeat this exercise every four
weeks until she improves and you change your mind, she leaves on
her own, or your boss sees enough to fire her. Protect your own
reputation as a supervisor by acting like a friendly mentor (even if
you’re gritting your teeth inside). Be seen as putting the organization’s
needs first, at least in public rhetoric. Be sure not to take your
frustrations out on your family. Keep a calendar countdown to six
months, the outer limit of deciding. You’re already halfway there.