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For reasons explained in this question, I am currently looking for a new place of work. I have recently received a verbal offer from a hiring manager and have been told that a written offer will be forthcoming sometime this coming week, for a start date in early-to-mid June. I fully intend to take this offer; however, for personal reasons, I will absolutely need to take two weeks off in the middle of January 2016 (a mere six months after I join). It is unlikely I will have accrued enough days off by then to take that much time off (as I mentioned, I do not yet have a written offer, so I am unsure as to the specifics. However, from what I have heard from friends who work at this company, I will not have enough vacation time by then).

When do I bring this up? Do I bring it up now, before the written offer is sent? That way, I can get an idea of their vacation policies up-front; on the other hand, I don't want to give off the wrong impression by asking about vacation times before I even have a written offer. Do I wait until after I get the offer and try to negotiate the time off then? Or even wait until after I've started?

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When do I bring this up? Do I bring it up now, before the written offer is sent? That way, I can get an idea of their vacation policies up-front; on the other hand, I don't want to give off the wrong impression by asking about vacation times before I even have a written offer. Do I wait until after I get the offer and try to negotiate the time off then? Or even wait until after I've started?

Bring it up now.

You have a verbal offer. That means the company wants you to join, and presumably you do, too. Now is the time to learn the specifics about the benefits, and to disclose your need for two weeks in January, and anything else you need that may not yet be offered.

Since you indicate that you "absolutely need to take two weeks off", I assume that this is a deal-breaker for you. So there's no sense in worrying about a "wrong impression". If you can't get the two weeks, you'll need to find a different job anyway. That's something you want to learn now.

For many shops, this won't be as big a deal as you might imagine.

Six months down the road, you may have accrued enough time off, or you may be able to "borrow" time off. For other companies, you may need to take your two weeks off without pay. Presumably, that wouldn't be a problem for you.

For some companies, in some positions, those two weeks may simply not be permitted. In that case, you need to know that now, rather than being in a awkward position later on and having to leave a job after six months.

Don't wait. Talk about it now, while you are discussing overall benefits.

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    I've been in this situation a couple of times, raised it at the verbal offer stage as Joe suggests, and it has gone smoothly. Both times the new employer allowed me to go negative on my annual leave balance, although I'm sure you'll find different customs in different countries. – Carson63000 Apr 26 '15 at 21:47
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You wait until you get the written offer and negotiate the time off as part of your package. Most decent companies will be ok with you taking a planned vacation if you let them know then.

If it is unmoveable, you may find it easier to negotiate if you share the reason (this of course depends on the reason). If you have unrefundable tickets, make sure they are aware of that as well. You may have to take leave without pay or they may advance you the leave.

The worst action to take is to wait until you start. Then it is less likely that you will get the leave. Lots of people ask for this sort of thing, a decent company won't be upset by you asking and well a company that would, then you have dodged a real bullet and can turn down the offer.

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I was in this situation, planning to get married about six months after starting with a professional firm, a small business. I brought it up at my second interview. My future employer was very pleased that I felt comfortable bringing up the concern, and agreed to give me time off. In fact, in the offer letter, my employer clearly stated that I would be granted paid time off for my honeymoon. Both you and the prospective employer deserve respect, and asking politely early in the process you are complimenting the company and manager, trusting they will not embarrass you or be dismissive of your honest concern about being allowed time off. Any experienced supervisor understands how awkward it can be to ask for something extra when a hiring decision is imminent; it demonstrates a certain bravery and confidence that your important needs will be considered. You should not expect them to allow your time off, and if it is declined, thank them for your consideration. Who knows, some issue may arise in the next six months which forces a change in your personal plans anyway.

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