my boss demands to know how I’m spending my time off before he’ll approve it

A reader writes:

My boss has requested that I write to ask permission and give a reason why when I want to take annual leave. I don’t have a problem with this, so I wrote with the reason being “personal matters.” He wrote back saying, “I would appreciate a slightly more detailed reason for your request regarding ‘personal matters.’”

Surely I am entitled to some privacy and would had thought personal matters means exactly that, personal! The thing is, I want the time off, which I have accrued over the year, to look for a job abroad. I don’t really want my boss knowing yet though, as he has a vindictive nature. Do I make something up instead? I thought of saying my personal matter is medical related, as this is not entirely false. If I stay working there much longer, I am likely to die of depression! The job hunt would be preventative measures.

Your boss is totally out of line. You’re entitled to use your benefits — which are part of your compensation — without having to justify to him that your reason is good enough. Do you also have to provide a list of how you plan to spend your money in order to receive your paycheck? No. Same thing here.

It’s none of his business why you want time off, assuming you have it accrued, which you do.

But that’s just the law of Sane Person Behavior, not actual law. Under actual law, there’s nothing to stop him from doing this. And he’s pushing for an answer, so you have to say something. You have three options:

1. Act if he must be asking for a legitimate reason. If you were requesting time off at a particularly difficult time, it would be reasonable for him to inquire about whether you were flexible on the timing, so act as if that’s what’s happening here. For instance, you could say, “Oh, is that a bad time for me to take? I’d like to schedule a week off sometime that month — is there a better one?” If that fails, you could then move on to #2 or #3.

2. Point out that his request isn’t reasonable, by calling out what’s he’s doing. For instance, I might say, “I think I must be missing something here. Our benefits package includes X weeks of vacation time per year, regardless of how we plan to spend it, but your email made me think you see it differently. Do you really require that I give you a detailed reason of how I plan to use my paid time off?”

3. Give a reason that’s true but vague, such as”I have a family thing going on.” (We can reasonably consider your need for time off to be something that involves your family.) I’m not fan of indirect answers, but I also don’t believe you’re obligated to answer questions that are legitimately none of his business, and there’s a power dynamic here that might require you to say something. (Or, as people have pointed out in the comments, there’s no reason you can’t just say, “I’m planning a vacation abroad,” which is true.)

This dude is ridiculous, and you have my full blessing on conducting a vigorous job search.

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