my young employees keep asking to take last-minute time off for surprise vacations

A reader writes:

This year, several people in my reporting line have asked for last-minute vacation days because a partner or friend “surprised” them with a trip or event – already booked and, of course, non-refundable. Each time we’ve bent policy so they don’t lose out, but it’s starting to feel like we’re rewarding poor planning (or very confident gift-givers). One person has even done it twice!

Everyone making these requests is in their early 20s, while I’m over 40 and feeling more curmudgeonly every day. Is this a generational thing – maybe inspired by TikTok surprise reveal culture – or just pure luck that I’d never encountered it before?

What really gets me is that they treat these situations as if they’re out of their control – “I didn’t book it, so what can I do?” It feels like they’re outsourcing responsibility for their choices to me. Of course anyone would rather skip work and do something fun, but isn’t part of being a professional recognizing that you still have obligations to your job?

Should I start saying no to these last-minute requests, or would that make me a heartless boss?

I don’t think it’s a generational thing, although I think it might be a young, inexperienced person thing — meaning that the reason you’re only seeing it from employees in their early 20s is because they’re still learning work norms and don’t realize this won’t usually fly.

And of course, every time you do let it fly, you’re inadvertently teaching anyone watching that it’s maybe a reasonable thing!

Which doesn’t mean you should deny the requests on principle. If you can accommodate a last-minute request like this without significant hardship, you shouldn’t refuse it just because of how it unfolded. But it’s also okay if you can’t! If you can’t say yes because of the impact it would have on your team’s work, you can say, “I’d love to be able to approve it, but you committed to the client to do X on those days and we can’t back out of that” or “I’d love to say yes to this, but two other people already booked that week off and we’re counting on you for coverage” (or whatever the case may be).

That said, it doesn’t feel great to tell someone, “Sorry, you have to say no to an already paid and non-refundable trip someone just gave you.” You have the standing to say that — and in some cases it will be the only reasonable response — but of course you’d rather avoid it if you can.

Ideally, after the first time this happened, you’d take it as an opportunity to clarify with your whole team what can and can’t be accommodated, and remind them of how much notice you need to be able to reliably grant time off. And if you do say yes to a last-minute surprise vacation, it’s smart to say something to that person like, “I’m going to find a way to make this work, but it’s got to be a one-time thing. Normally we’d need more notice because of ___.” (Filling in that blank is important. You should be clear that it’s an issue because of coverage needs, or a looming and important deadline, or you were relying on them to fulfill a commitment they’d made, or whatever it is, so that it’s clear this isn’t about rules for rules’ sake, but something with an actual impact on your team and their work.)

It’s not too late to do that now! You could let your team know there’s been an increase in last-minute requests for time off and so you want to make sure that people know that you need X amount of notice to be able to reliably approve time off.

Don’t say no on principle but, since you’re seeing misaligned expectations, do proactively educate people about how it doesn’t and doesn’t work.

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