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I would like to plan travel ahead of time, but my supervisor makes that pretty much impossible.

Try this first: “Bob, I’m having trouble using my vacation days because of the delay between when I ask and when you respond.

Often, my supervisor will take days off (either for personal reasons or for his second job) and inform me the day before so that I know I’ll essentially be in the office alone (GAs work 20 hours a week).

Some managers would absolutely want to know that a manager under them was doing this; others would consider it a breach of chain of command. I am currently a contractor doing web development work.

You really need to know the players to answer this one. I have been in this position for over two years now.

I am one of the two full-time professionals, and the other full-time guy is my supervisor.

We don’t have an admin assistant, so office coverage is very important in our office.

Is it better to ask in person or submit the request differently in some way?

” If that doesn’t work, whether or not to go over his head depends on the dynamics there.

You can certainly press them, ideally as a group — saying something like, “We’re uncomfortable with Cecil’s wife continually coming here and causing disruption.

We feel unsafe, and we’d like you to ensure she’s no longer allowed on the property.” But ultimately, it’s their call.

It’s pretty much a given that if I ask for time off, he’ll avoid answering me until the week of, after I’ve asked at least 3 times.

For the most part, there isn’t a reason why I wouldn’t be able to go on vacation on a certain day.

It’s pretty weird that they haven’t already taken steps to deal with this though.