Should I Ask for Paid Vacation When Starting a New Job?

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After a year at their current job, an employee has decided to seek new opportunities and received an offer from a larger company with better pay and bonuses. However, they have a pre-booked vacation during Labor Day week and have informed the new employer, who is understanding. The employee is considering whether to request this vacation as paid time off or accept the income loss, as they have never navigated this situation before. The discussion highlights that many companies have policies regarding vacation accrual and usage, often requiring a certain tenure before vacation can be taken. It is suggested that the employee inquire about the new company's vacation policy and consider asking to use part of their allotted vacation time for the already planned trip, emphasizing that this request is not for additional time off but rather for the use of standard vacation benefits. Overall, it is deemed reasonable to make this request.
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I have been working at my current employer for about a year. About 9 months into the job things had changed and I decided that this was not the right place for me long term. So for I've been on and off looking around for other employment and finally something broke for me. I was given a job offer for a better position, larger company, more money, plus possible bonuses. Unfortunatly, I have vacation already booked and paid for beginning the week of Labor Day. I have already informed the new company of this prior obligation and they are very understanding regarding the time off. My question is whether I should press to make it a paid vacation or take the hit to my income (I can absorb it but honestly would rather not). I have never had to broach this topic before when changing jobs so I honestly don't know how reasonable it is to ask for the paid week. This is a great opportunity for me and would not want to ask for something that would just seem way off base. Any advice?
 
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Are you already working at your new job, or are you going to start right after your vacation?
 
No, I would work 2 weeks then take the week off.
 
Many places have policy about how long you must work before you can take a vacation (often not before your probation ends), as well as at what rate you can accrue vacation days (often a fraction of a day per time-period, such as 1.25 days accrual per pay period).

You could ask what their policy is regarding vacations, and yes you could ask if, since it is already booked, you could use a week's vacation allotment in advance. But of course you're not asking for this as extra time, right? You're simply asking for part of your normal vacation time (probably 2 weeks per year) to be used right away.

It is not unreasonable to ask.
 
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