Play by the Rules
Before you prepare your social calendar, check out your employee handbook to understand your company’s guidelines on vacation days. “Making certain your vacation request aligns with company procedure is a good start when asking for time off,” says Susan Lucas-Conwell, CEO of Great Place to Work.
Take a look not only at the number of vacation days, but when and how they accrue, and whether they roll over from year to year. If you’re new to your company, check out when you’ll be eligible to take paid days off, and whether seniority plays a factor in scheduling.
But perhaps more importantly, try to get a feel for how vacation time is perceived around your department. Do your colleagues stretch out their days throughout the year, or is it really OK to plan a three-week trip? Knowing the rules—both formal and informal—will help ensure that your request won’t be frowned upon.
Plan Around Work
Your next step is thinking about what makes sense in terms of your workload. “Are there any major projects, events, or deadlines during or directly after the time you want to take off?” says Amanda Augustine, a job search expert for The Ladders. “If so, consider pushing back your vacation dates so you can be there to finish preparations and meet your goals.”
Also think of your colleagues’ needs and workloads, and how your vacation plans may impact the work of the whole team. “If you have to close the books the last week of every month, that’s not a good time to ask for vacation,” explains Lynne Sarikas, director of Northeastern University’s MBA Career Center—someone else will certainly have to cover for you, and may not be prepared to do so.
Give Plenty of Notice
Once you’ve settled on some target dates, you’ll want to give your boss sufficient lead time with your request. Remember, just because you’ve accrued paid days off, doesn’t mean you can use them at whenever you’d like. Whatever you do, “don’t present your request as a demand,” says Sarikas. Instead of telling your boss you’re planning on a certain week, suggest that you’re trying to make plans around that time period and would like to see if you can take it off.
And a word to the wise: Even if you want to book that sweet hotel deal before the deadline passes, going ahead with your plans sans your boss’ agreement is never a good idea. “If your manager needs you in the office, you’re now in a sticky situation,” says Augustine. Plus, “It looks like you’re undermining your boss’ authority.”
If you have a date you must keep—say, attending your sister’s destination wedding—Sarikas advises giving as much notice as possible and coming up with solutions for coverage. “Your manager will be more likely to let you take the time off when you can show him or her that nothing will fall through the cracks,” says Augustine.
Pick a Good Day
Like anything, how your boss responds to your message often has everything to do with what else is on his or her plate. Read: It’s not a good idea to bring up your two weeks in Hawaii when your boss is already in a bad mood or coming off a day of back-to-back meetings, Sarikas says.
Instead, try to make your request during a regular face-to-face meeting. If a brief chat is tough, or if you work remotely, Executive Coach Kathi Elsterfinds it best to email your request to your boss for review. “Be considerate and find a time when you know your boss would be in the right frame of mind.”
Accept Your Fate
Of course, even with advance planning and a well-timed ask, there are many reasons your request can be turned down—peak project periods, limited staff resources, or a need to avoid having the whole team out at once—so be prepared for things to not always go your way. The bottom line: Says Sarikas, “The fact that your manager can say no makes it more important to ask as early as possible and in a respectful way.”