Dear Jewish Fairy Godmother:

My supervisor’s teenage son is working at our company part-time this
summer and reports to me, which is no picnic. The kid has been raised
with lots of affluence and little work ethic. He has the attention span of
a fruit fly. It’s taking a lot of productive time out of my day to deal
with him. The worst part is that the supervisor thinks he’s doing me a
favor because his son is my “helper.” How can I skillfully navigate this?
Mentor (Ugh)

 
Dear Mentor:
This sounds like it’s been going on for at least a week, which is a
pretty reasonable time for you to meet with your supervisor for an
interim debrief. Assuming you want to keep your job, use none of the
explicit language you wrote me, though if you’ve been hankering for a
layoff and unemployment, the universe has just offered you a great
gift.

 
Ask the supervisor/father what his expectations are for his son’s
summer. Ask if this is mostly a way to introduce him to the obligations
of a regular workday or if there are specific skills he’d like him to
learn. Ask him “candidly and confidentially” what he thinks are his
son’s greatest strengths and weaknesses, and which if any he’d like
your help addressing in your role as immediate mentor. Go lightly on
the idea that having him around reduces rather than enhances your
personal productivity. But make it clear that you’re focusing on helping
the son in addition to your regular work. Ask if there is any specific
task that Dad would like to work with his son on directly, or other
people in the department whose expertise and work style would also
be good role models, so that the son can have the benefit of
accountability to and mentoring from more than one person.

Lastly,
ask if Dad would like to treat the internship the way the company
would treat any other new probationary employee, with at least an
informal three-month evaluation, to give him feedback that’ll serve
him well when he is in a potentially less supportive environment.
The biggest danger is of course that your boss will overhear you
griping about his son to colleagues, or that one of them will say things
that are attributed to you. But as long as you have an ongoing
dialogue with both father and son, you should be okay.

One last thought: don’t assume this kid is merely a worthless brat. Ask
him flat out if he’s there to learn how to be a good employee and a
future manager, or just to appease his father. Then treat him like
someone worthy of a little respect and invest your time and energy as                                    you would with any other raw recruit, with patience and a sense of
humor.

PS: Go home and have a tall cool one.