Ask the Expert: How Do I Ask for the High Holidays Off?

What's the best way to approach my boss?

Question: I’m at my first job out of college, and I’ve been working there for about two months. Now the High Holidays are coming up, and I’m nervous about talking to my boss about all the days I have to take off.

Someone in the office suggested I ask that the days can be not counted as vacation, but I’m not sure how to do that. Even if I take them as vacation, I’m concerned she’ll think I’m slacking off if I take so many days in one month. What’s the best way to ask my boss for the High Holiday (and Sukkot) days off?

–Craig, Madison

Answer: Congrats on your job, Craig! I know how nerve-wracking it can be to ask your boss for something when you don’t feel like you’ve developed a reputation for yourself yet. But if you’re able to handle the situation responsibly, the High Holidays are actually a time when you have an opportunity to prove yourself as a conscientious worker.

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Obviously, this answer depends on what the policy for personal and vacation days is at your office. If someone at the office thinks you might be able to get the days off without dipping into your vacation then it’s probably worth it to at least ask. Of course, it also depends a lot on what kind of person your boss is and what kind of interactions you’ve had with her in the past. If you know she worries that people aren’t productive enough, or that people are leaving too early in the evenings, or coming in too late in the mornings, it’s a good idea to keep these things in mind as you plan how you’re going to address the issue. But assuming you don’t know your boss that well, there are still some basics you can and should cover.

First, provide straightforward information. Say, “You probably know I’m Jewish, and the High Holidays are coming up in a few weeks.” Mention the exact dates you’ll need to have off, and explain that you’ll be at services during those days (if you have plans that don’t involve services, you can just say you’ll be observing the holiday). If you’re asking for the first days of Sukkot, as well as Shemini Atzeret and Simchat Torah, you can expect to have to explain those holidays a little. Initially, give only the basic information, but offer to give as much more as your boss wants, and I personally recommend telling your boss she can find out more right here on My Jewish Learning.

Next, outline your plan. Which means, of course, you need to have a plan. If you’re hoping to take the days as vacation days then you want to reassure your boss that you’ll get all of your work done ahead of time and give her an explanation for why you’re taking your time in two-day chunks. If you’re asking if you can have the days off and not to have them count as vacation days, think about creative ways you can get your work done early, and other times you may be able to make up your hours. Can you come in on a weekend? Can you work later for the weeks leading up to the High Holidays? Can you offer to come in at a later time when you know a lot of other people in the office will be out?

I spoke with Rachel Bliner, an observant Jew and relationship manager at Management Leadership for Tomorrow about how she approaches her bosses when she starts a new job. She advised, first of all, that you let your superiors know as early as possible that you’ll be taking time off for Jewish holidays. That way, they know to expect it, and they know being an observant Jew is part of your identity. Rachel said, “I think it’s really important that you highlight other places where you plan to pitch in, and really go above and beyond.” She also said, “Acknowledge that it is a lot of time off, but if you tie it to religion, most people will be respectful of that. In my experiences, colleagues have always been respectful and understanding about religious practices.”

Remind your boss what a good employee you are. Feel free to say, “I know you liked what I did on X project, and I’m excited to do more work like that.” Personally, I often offer to take on an additional assignment at this point if my boss thinks it’s necessary. I have never been given an extra assignment when I offered, and I think it shows that I’m not trying to play the system.

Point out that you’re bringing this up way ahead of time in order that you can come up with a plan that seems workable to your boss and you. Offer to be flexible about some things, and be clear about the things that are musts for you (“I’d be happy to work from home on Sundays this month, but I cannot be in the office at all on September 9th or 10th.”)

Really listen to how your boss responds here. If you’re still getting some pushback, try to identify what the specific concerns are and offer to think about ways to get around them. If things seem fine, say thank you and skedaddle.

Finally, make sure you follow through. Stay late if you said you would, get your work done ahead of time, and make sure that you’re on top of whatever you said you’d be on top of. When you do this, you end up proving yourself as a more responsible and conscientious worker than if you hadn’t taken the days off at all. It also gives you a good precedent for when you want to ask for days off for Passover, Shavuot and the High Holidays next year.

Good luck!