Dear Ann Cannon • Early last year, my best friend of many years asked if I would hire her daughter at my place of employment where I’m a midlevel manager. I did so happily. I’ve known this girl (a woman now) since she was a baby. She’s creative, bright and well-educated. But it turns out that she’s a bad employee — never on time, always pushing deadlines, etc. And she doesn’t take correction well, either. She’s been known to sit in my office and cry when I talk to her about her performance, then refuses to respond to emails or texts afterward. Because she’s very good at her specific job, my boss would like to keep her onboard. But he’s putting a lot of pressure on me to fix things — as though I’m the one not doing my job. Help! What should I do?


Dear Babysitter • Wow. An already difficult situation — dealing with an employee who isn’t doing her job — is made more difficult because of the deeply personal connection you have with her family. No doubt about it. You are in a really tough position. So what can you do? These options come to mind.

  1. Hope she quits.
  2. Quit yourself.
  3. Pick up the slack and cover for her.
  4. Talk to her about her lackluster performance. Then help her set goals for improvement and follow through with regular one-on-one conferences.
  5. Fire (gulp!) her.

OK. I don’t really advise the first three options. Hoping she quits would just be wishful thinking on your part, sort of like hoping the folks at the IRS were just joking when they said they’re coming after you for all those back taxes you owe. And unless you really hate your job and have another employment opportunity lined up for yourself, why should you be the one who quits? As for the third option? Yeah. You’re right. It’s stupid and unrealistic. And did I also mention stupid?

The fourth option can be a good one. But it sounds as if you’re already doing this and that it’s not working. Furthermore, it’s not a sustainable solution. Which brings us to the dreaded fifth option: fire her.

I know if I were in your position I’d want to do anything BUT fire the daughter of my best friend. I’d justifiably worry about the consequences. Will my friend understand why I took this action? Will our friendship remain the same? Will our friendship even survive? Gah! So much to worry about!

However. I think you need to ask yourself this question: Bottom line, is this employee harming or helping the overall health of the company — a company made up of many individuals and not just this single employee who, by her unprofessional behavior, is demanding special favors? Sometimes loyalty to one person makes us blind to the well-being of a larger community whose members depend on it for their own well-being.

In the long run, losing a job may actually be a good thing for your friend’s daughter, frankly. It could be a much-needed wakeup call for a clearly talented young woman who still needs basic lessons in “adulting.”

I’m sorry. You’re probably in for some stormy weather. But, as Led Zeppelin (and also my dad) used to say, good times, bad times — they too shall pass. Hang in there.

Dear Tribune Readers • Meanwhile, I heard from readers about Underwear Man. Here’s a sample response.

If this guy is hanging out on his front porch in his underwear, he needs to be called on it. Tell his wife? Do you think she doesn’t know? Tell him, “If you want to talk to me put some damn pants on, you pervert!” Why do women think they need to pussyfoot around with these idiots? He knows very well that he’s causing her some discomfort and he loves every minute of it! Just sayin’.

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