Ask a Manager

A reader writes:

I work at a small start-up company, and when I accepted the position my boss represented one of the perks as “we can be informal about vacation days.” I’m not a slacker and didn’t plan on taking advantage of it, but understandably I was happy about the attitude.

However, in the seven months since having worked here, I’ve taken a total of 2 vacation days for long weekends (I started accruing after 3 months), and 1 sick day. Every time, my boss has had a very “You’re slacking” type of attitude and seemed unhappy that I was taking time off. Another employee here (who granted is more senior than I am) took a 2 plus week vacation in a foreign country and seems not to get any flak at all.

My boss even asked me to fill in HR forms for the two vacation days (we have a parent company with an HR dept), and said it was the first time he had even seen the forms. In other words, the other employee hasn’t reported any of his time off.

I feel that the disparity in treatment is unfair, even if the other employee is more senior, and that the company’s attitude was misrepresented as least as far as I’m concerned. I’ve been working just as hard and putting in as many hours as everyone else here. Should I bring it up with my boss?

Yes. You need to find out what your boss’ expectations are and how this is all supposed to work.

I’d say something like this to him: “I want to make sure I’m on the same page as you about time off. I might have misinterpreted, but I got the sense that you might have frowned upon the three days that I’ve taken off since I started. Three days in seven months doesn’t seem excessive to me, but I wanted to check in with you and find out what your expectations are about how time off is handled.”

It’s possible that by asking about it directly, you’ll find out that he really doesn’t object to you taking a reasonable amount of time off (time that you note you have accrued, after all — i.e., earned). Maybe your boss is just grumbly when people do because it stresses him out, but he doesn’t expect to stop you from doing it.

It’s also possible that you’ll find out that yes, he did indeed misrepresent the time-off policy when hiring you. Or that he has some unspoken expectation that you won’t take any vacation during your first year. Or all kind of other unreasonable possibilities that you can only really find out about by asking him.

Here’s another possibility: Maybe his concern wasn’t with your days off per se, but with your timing. For instance, if you were taking vacation days in the midst of an urgent project, that could explain his reaction. You’re at a start-up; workload tends to be high and there can be a no-time-off ethos during certain periods.

Or maybe when he told you that people are informal about vacation days, he meant that people will take a day off if they work over the weekend — but you hadn’t done that when you took yours. Again, it’s a start-up, so who the hell knows what’s up, but it wouldn’t be shocking to have that be part of the culture there.

In any case, no matter what the explanation is, the answer is to ask. Ask with an open mind, non-defensively, and see what he tells you.

If his answer reveals definitively that he misrepresented the policy when hiring you and/or that he doesn’t really want to see you take time off ever, then you need to address that head-on. Again, do it politely and non-defensively, but assertively and straightforwardly. For instance: “My understanding is that I earn three weeks of paid time off a year, and I accepted the job with that understanding. I think it’s important for people to have occasional breaks from work, and I know it helps my productivity. I want to respect the company’s needs too, of course, so what times of year are better ones to take it?”

By the way, I’d leave your coworker out of it, since really this is about you and the treatment you get, period. For all we know, your coworker negotiated special arrangements for vacation time; whatever is going on with her is irrelevant to the real issue here — which is whether or not you and your boss can get aligned on how this is going to work for you.