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When is it appropriate to tell a new employer about a holiday/vacation that is already booked? Especially when it is close to the start date of the new job.

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If the planned holiday is soon, then you can do it when negotiating your start date. You can cast it as "I have this trip planned; should I start after I get back or can we talk about my taking the time off?".

If the planned holiday is some months away, but will occur before you will have accrued enough vacation time to take it, then bring it up when you're discussing compensation. Tell them about the trip and ask whether you can go negative (spend vacation time in advance of earning it) or take unpaid leave for this trip. I have done this (with the result being "go negative") and I have had many coworkers do it.

If a company wants you to join them, then in the grand scheme of things your two-week vacation just isn't a big deal and they will generally want to work with you to resolve the issue.

Even if you will have enough vacation time built up, it's a good idea to share your plans with your manager as soon as you can.

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    This is really good advice. If a company wants you, provided you don't make a habit of it, in the end your vaction time is your vaction time. The important thing is to make it clear what your plans are.
    – Donald
    May 16, 2012 at 11:25
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    @Ramhound, as for making a habit of it, starting a new job with an already-planned vacation will happen just once (for that employer). I'm not suggesting that someone get in the habit of making vacation plans before clearing the dates with his management. :-)
    – Monica Cellio
    May 16, 2012 at 14:28
  • Before asking to "go negative" or offer for it to be unpaid leave, try to get them to just bonus you the vacation time. I've found that timing (and amount) of vacation days is one of the easiest things to negotiate.
    – NotMe
    Oct 22, 2014 at 22:09
  • I've done that on my second job, had three weeks off in August with a contract starting mid-july. I warned while being recruited and took unpaid leave. If you're not recruited for a very urgent project, having people leaving for holidays is something normal in a company and it shouldn't bother much.
    – Jemox
    Jan 15, 2019 at 23:26
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If you don't mention this before you accept the offer, the likelihood is that the time may not be approved as you do not have enough earned vaction time. If you have already started the new job, it is already too late.

Further, be prepared to take this a leave without pay even if you mentioned it up front. However, in your salary negotiations you should mention it and negotiate for the leave to be with pay. YOu may or may not get that and then you have to decide, but most companies will be accommodating for plans they knew about before they hired you.

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I disagree with the above. When you start a new job, you should not be thinking about taking a vacation. Even if this is a trip that you had planned before perhaps being laid off at a previous position, you should not expect a future employer to honor already made vacation plans. You should just cancel your plans and accept any monetary loss. When you go to apply for a job, your main objective is to make a positive impression on your future employer. Insisting on taking a vacation that you had already planned will communicate that you only think of yourself.

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    Re:" Insisting on taking a vacation...only think of yourself." OR it communicates to your new potential employer that you are not a robot, you are a person who has a life outside of work.
    – Dunk
    Oct 24, 2013 at 19:30
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    "Insisting on taking a vacation that you had already planned will communicate that you only think of yourself." What do you think you will communicate to your family members if you cancel a family vacation for a job?
    – GreenMatt
    Oct 24, 2013 at 21:27
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    I would absolutely, one hundred percent expect a potential future employer to honour existing holiday plans. Otherwise, that potential future employer won't become a future employer.
    – gnasher729
    Sep 29, 2014 at 10:03
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    I have known many people who had vacation plans at the time they got a new job and in every case, the employer was able to accomodate them or they didn't take the job. This is an ordinary thing to most employers if you tell them about it up front (they can get justifiably cranky if you don't.). And who would want to work for someone who would expect you to give up your long planned and paid for vacation? I'd count on that employer expecting me to do it again when I try to take vacation later on. I would also count on that employer trying to exploit my personal time in many other ways as well.
    – HLGEM
    Oct 22, 2014 at 20:23

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