When to ask for (unpaid) time off at a new job?

I would bring it up now. Earlier the better, you’re not looking for a ton of time off and this way your bosses have plenty of heads up.

I had the same situation - the only difference being I was able to use PTO before the 6 months because it was a wedding and not just a vacation (they offered some flexibility for this sort of thing). The first question I have is - do they have any kind of policy for how far in advance requests for time off should be noted? Next - Is it a popular weekend for people to want time off? If there's no time window and it's not a popular time for people to take off, then I would say you can shoot for after your 90 days. But if you're worried that 3 weeks may be cutting it close, I'd say to just bring it up the next time you have a conversation with your boss(es). For me, it was a matter of waiting until the right time to bring up the wedding, and then it flowed naturally into what I would need to do to ask for time off. (I started the job in June, got married in October.) I didn't want to jump in too early because I didn't feel like I had built up a relationship of any kind with my bosses, but I didn't want to wait until the last minute either. So I just waited for what felt like a "good time" to talk about it.

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That's what I'm struggling with. I feel like I haven't really built any kind of relationship with anyone here yet so it feels weird just bringing it up and asking for time off but I also don't want to wait until last minute. I believe it's just the standard two weeks in advance for time off requests and I don't think it's a popular weekend for time off. It's not a holiday weekend or anything, however, it is summer so I'm sure people are more likely to ask for PTO than during other seasons.

If you think they're laid back, I would probably ask sooner than later. You could also ask a coworker what are the chances that they will let you take unpaid leave.

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I agree with this. I'd wait a little longer to build a relationship with your boss(es). Then you'd get a better feel on when to ask.

A lot depends. Are there busy times in your department? Do people with more security get priority? Even if you offer to take time off without pay, others may resent you. What if everyone else has asked for that time?

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So what are you suggesting I do? I would still be here for any busy time that month, it's only 2 or 3 days not a week.

I would ask now, they can’t fire you just because you want 3 days off for your wedding.. I understand the probationary period but if they were to fire you for that reason that means they’re just looking for a reason.. talk to them and be honest... not too much though lol..

I would bring it up right away. If you think they will definitely say yes, I think they would prefer to know sooner rather than later! I started a new job in June 2018 and my wedding is June 2019. I went to my boss literally in July 2018 (1 month into job, 11 months before wedding) to tell him the day I was getting married and to confirm that it'd be ok for me to take time off around then, especially before I booked my honeymoon flights.

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I'm pretty sure they will say yes. It's hard because I don't feel like I've formed a relationship with anyone here yet so I feel weird just bringing it up and asking for days off but I also don't want to wait and then not be able to or have them be upset I waited so long. Our vacation policy literally says, "eligible to use or be paid for vacation after 6 months of employment." So I take the "be paid for" part as it not being a problem to ask for it unpaid.

My FH just went through the same thing. I kept telling him he should’ve brought it up during the interviews but her felt it was better to “ask for forgiveness rather than permission” anyways he wanted to prove he was a good worker before he asked for time off. He asked for the same as you. Just three. Days. He did mention after he was hired that he was getting married and then maybe two weeks ago kind of quietly put the time off on their calendar. It just got approved yesterday. It’s a tricky spot because you want to give them as much notice as possible but also don’t want to be the new guy going hey give me this time off. It sounds like they’ll be pretty understanding so I would go with you gut.

This post is really helpful for me! My FH and I just moved across the country for his new job and I'm searching for a new one and my wedding is in June.

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Yeah I think I'm going to wait a few more weeks-month since I do still have some time and then I will go from there. I feel like I need to still "prove myself" a little more before I would be comfortable asking for time off. I guess I don't really need to ask for all three days, I really just need that Monday after but it would be nice to have 2 or 3 days to get everything organized before and after the wedding before worrying about work again.

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If you're comfortable mentioning it during your interviews, I probably would. I personally did not feel comfortable bringing it up when I interviewed for this position as it is a really competitive job to get so I didn't want to hinder my chances in any way. However, if you feel like you can bring it up in your interviews, I would.

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Thank you for the advice, Future Mrs. K!!!

Does you department keep a list of PTO schedule? Can you see if others will be out, or if a black out period

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No we don't

I'd probably wait until you are 90 days in, unless waiting 90 days makes it really unreasonable to ask for 3 unpaid days off. If you still have some buffer though, you should be good.

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I agree, I'm thinking about just waiting until the probationary period is up. It's only 2 or 3 days, I think 3 weeks ahead would still be plenty of time and I would feel better having that 90 days in before asking for any time off.

Just for future knowledge and for anyone reading this, I'm in HR and the appropriate time to bring up any planned vacations is after an offer is extended but before it is accepted. It doesn't need to be brought up during an interview, but if a company is offering you a job they will likely work with you on it so that's when it's good to let them know.

Since that isn't the case here, I personally would ask sooner rather than later. Given the circumstances, any decent person would happily grant the unpaid time off for your wedding weekend. I think that asking for three full days off only a couple weeks out is last minute if they know it's something you could have asked about sooner (and they'll know you purposely waited when they realize it's for your wedding). Different companies have different policies on how much notice you have to give for time off, but I always operate under the sooner the better.