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Advice / Succeeding at Work / Changing Jobs

How to Ask for Time Off at Your New Job (the Right Way)

Ah, summer. The time of year when your thoughts turn to tan lines and drinks with little umbrellas in them—unless, of course, you’ve just started a new job. In which case, you’re probably staring jealously at your friends’ Instagram pictures and wondering how you’re going to survive the summer without going on a single trip.

The good news is, just because you’re a new employee doesn’t mean you have to give up your travel plans. To get the scoop, read on for answers to some of the most common questions about taking vacation at a new job.


I just started a new job—when is it okay to take a vacation?

After I graduated from college, someone gave me a piece of advice I always abide by: Don’t ask for any time off during the first three months of your job. Think of it as a probationary period in which you’re trying to prove your worth—which is hard to do if you’re sipping margaritas on the beach.

After you’ve been at a job for three months, you’ve likely accrued a little vacation time and you’re ready for a break from the 9-to-5 grind. At this point, it’s usually acceptable to ask for one day off for every month you’ve worked after your self-imposed “probation.” (Obviously, this varies depending on your company’s time-off policy and how much vacation time you’re given.) In general, though, if you started working in March and didn’t take any time off in March, April, or May, you’re not going to raise any eyebrows if you ask for a day or two off in July.

The exception to this rule comes if you’re working at a company that’s super-relaxed or touts vacation time as a major perk. Some start-ups and small companies can’t pay their employees high salaries, so they try to make up for it with flexible schedules and lots of vacation days. If you’re not sure what your company’s culture is, look for some common cues. Has your boss asked you what trips you’ve got planned for the summer? Are other new employees taking a long weekend over Independence Day? If so, you may be okay to bend the three-month vacation rule a bit.


I’ve been at a company for a few months, but I’m still getting the hang of things. How can I determine the best time to book my trip for?

As a new employee, the last thing you want to do is book a vacation during the busiest time of year or find out that your days off conflict with a critical meeting. So, do some research before you start looking at flights. If you’re not sure when your company’s busy season is, ask a fellow employee.

You can also bring it up with your boss (and should, in most cases). A simple, “I’d like to use some of my vacation days this fall, and I’m wondering what the best time to be out of the office would be,” will help you schedule a stress-free vacation and show your boss that you take your job responsibilities seriously.


My boss is a little intimidating. What’s the best way to approach her about taking vacation time?

If you have a no-nonsense boss, it can be a little scary to ask for vacation, even if you’re entitled to time off. To make sure the conversation goes as smoothly as possible, broach the subject at the right time, like after you’ve wowed your boss with everything you’ve accomplished in your weekly status meeting or on a quiet Friday afternoon when she likely has time to chat. And definitely ask for the days off, rather than tell her that you’re taking them. A simple, “I have three vacation days, and I’d like to use them the week of September 9. Is that possible, and does that work for the team?” works perfectly.

After you’ve gotten verbal approval, document the vacation on your calendar and send your boss a reminder a week or two before the big day that says something like, “Just a reminder that I’m going to be out on vacation Monday through Thursday, but I’ll get that report to you Friday afternoon for review.” This lets you kill two birds with one stone: You’ve made sure that your vacation is still on your boss’ radar, and you’ve let her know that you’re working hard to get everything set before you leave.


My boss keeps sending me emails while I’m trying to relax on the beach. Do I need to respond?

Every workplace has a different expectation when it comes to staying connected on vacation. It’s best to ask your boss ahead of time what he needs from you before you leave the office and what he expects while you’re out of town. For example, does he want a quick update on the status of all your projects before you head out of the office? Will you need to check your email on a regular basis or just provide your boss with a way to reach you if any work-related emergencies arise?

If you didn’t have this conversation with your boss before you left, play it safe. Respond to important or time-sensitive office emails as best as you can, even if it means setting aside a few minutes each morning and evening for a little work. If your boss doesn’t need a response until you’re back from vacation, he’ll probably let you know.


I’m interviewing for a new job, but I haven’t been offered the position. When should I tell them about the vacation I just booked?

Unless your vacation is a trip to the Amazon that’s going to take you out of the country for a month, there’s no need to announce it until an offer has been made. Once the company has extended an offer, you can ask HR or the hiring manager if they can accommodate your vacation plans. Again, remember to be courteous and ask for—but don’t demand—the days off. If you end up accepting the job, you’ll want to make sure that you’ve started your employment off on the right foot.

In short, you don’t have to resign yourself to a boring summer just because you started a new job. By knowing how and when to ask for vacation, you can impress at your new job while still satisfying your wanderlust.


Photo of man relaxed courtesy of Shutterstock.