How to Manage Time-Off Requests This Holiday Season

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Paid vacation is one of the most important employee benefits, trumped only by healthcare, according to a 2018 study from the US Travel Association. That means employees prioritize vacation time over retirement plans, flexible work options, bonuses, and sick leave.

With the holidays fast approaching, you and your colleagues are likely itching to cash in your vacation funds. Employers are often flooded with time-off requests in November and December. As AAA reports, tens of millions of Americans travel for Thanksgiving every year, to say nothing of the myriad additional holidays that fall around this time.

As employees start vying for those coveted days off, things can get tense and chaotic in the office. However, with a few simple hacks, you can make the holiday season run much more smoothly for everyone involved:

1. Make Sure Your Time-Off Request Is Reasonable

Eighty-four percent of offices don’t close shop during the week between Christmas and New Year’s Day, according to SHRM. You and your colleagues may want some rest and relaxation, but you’ll need to balance that with your company’s need for people to keep its operations going.

When it comes to what constitutes a “reasonable” time-off request, HR expert Mikaela Kiner recommends first understanding the norm within your company. Is it unheard of to take more than a few days, or is the culture more flexible?

Another thing to consider is teaming up with colleagues when mapping out your requests. This is especially important if you plan to step away for a long period of time. Aside from pushing your rainy day fund to the limits, you don’t want to take advantage of your employer’s vacation policy.

“I always think it’s great if your team is set up where people can cover for each other, so maybe consider informally figuring that out with a colleague,” Kiner says. “That way, by the time you go to the boss, you’re coming with a solution. You’re saying, ‘I have 10 days off, but it’s going to be fine because I’ve arranged coverage with somebody.’”

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If you aren’t planning on going entirely off the grid during your vacation, that’s another detail that could sweeten the deal for your boss.

“It’s a different scenario if you go to your boss and say you’re going to be monitoring and responding to the critical stuff while you’re away,” Kiner says. “Then it’s less stressful for them.”

2. Prepare for Your Time Away

Someone has to hold down the fort in your absence. Kiner says the first order of business is accounting for any projects that will be underway while you’re gone. From there, connect with whoever will be managing those responsibilities and thoroughly brief them before you head out.

Doing this won’t just keep your projects going strong — it will also show your boss you’ve thought ahead and are making appropriate preparations. As a result, your boss will probably feel more comfortable granting your time-off request. Just keep in mind that your substitute may not be able to address every single thing that pops up. (They have their own job to do, too!)

“Take the pressure off [your substitute] by defining what’s really critical and time-sensitive, as well as the things that can wait until you return,” Kiner says.

3. Set Yourself Up for a Smooth Return

Transitioning from vacation mode back to the daily grind isn’t always easy. A 2018 survey from the American Psychological Association found that 42 percent of employees who take a vacation dread returning to work.

“This is so stressful for people, and sometimes people don’t like to go on vacation because they come back to that inbox that’s just flooded,” Kiner says. “One thing I like to do is block at least the first half of the first day back because I know I’m going to have a ton of catch-up.”

She recommends one other simple move that could ease the back-to-work scramble: using your last day of vacation to work from home. This way, you’ll have a whole day to get back on track, respond to messages, and digest any important details you missed while you were gone. The best part? No one will expect anything of you because you’re technically still out of the office.

“I don’t like that stress of walking in and not knowing what’s hanging over my head,” Kiner says. “The more you care about what you do, the more stressful it is to walk into the unknown.”

As a final note, make sure you know exactly how many vacation days you have left before you head out. The last thing you want to do is tack on an extra day only to find out it’s unpaid. Roughly a third of American households have less that $1,000 in savings, and you don’t want to have to dip into those accounts due to a misunderstanding.

Everyone deserves some time off this holiday season. The key is planning ahead so you can depart and return with as little stress as possible. Your team will thank you for it — especially your boss. Once you prove you can responsibly step away from work and transition back without a hiccup, your manager will be less worried about granting you time off in the future.

Marianne Hayes is a longtime freelance writer and content marketing specialist.

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