Advice / Succeeding at Work / Work Relationships

Ask a Candid Boss: How Do I Deal With My Entire Team Wanting to Take the Holidays Off?

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Dear Candid Boss,

With the holidays just around the corner, I want everyone to be able to take the time off they need—but we also have work to do. How can a manager account for everyone’s holiday plans while still making sure the work gets done?

Don’t Call Me Scrooge

Dear Don't Call Me Scrooge,

It’s that time of year when many of your employees want time off.

For lots of companies, this is also the busiest part of the year. At this point, you need extra hands on deck—not everyone disappearing. And yet declining vacation requests is hard. You don’t want to feel like the Grinch, after all.

Your goal is to find a solution that’s fair to all of your employees. Here are a few tips to make sure your team’s to-do list gets accomplished—while still letting your employees enjoy a well-deserved holiday break.

1. Let Employees Make Trade-offs

You can’t possibly know all the different plans everyone on your team is making over the holidays. Moreover, you don’t need to know—it’s far too exhausting and time-consuming to keep track of.

So, explain to everyone on your team what the coverage needs are, and then let employees figure out who will take care of what. Your job is to create a system that makes it really clear what is needed and when it’s required by—and then let your employees work out who covers for whom.

If you design a system that’s transparent and flexible enough that employees can swap out with each other without creating chaos, things will run much smoother for everyone.

Once you’ve done that, resist the urge to get dragged into the middle of every trade that employees make. Set the expectation that they need to work those things out fairly and amicably between each other. (Of course, if things start to go off the rails, you will have to step in.)

2. Don’t Assume

Remember, not everyone wants to celebrate the same holidays. Plenty of people were raised in other traditions and religions, meaning they might not even want the time off that you’re expecting they would. Additionally, there are people who simply dislike the holidays and would rather work.

If you can, offer people who don’t mind coming into the office during the holidays extra time off at a less busy time of the year. Let people who work on Christmas Eve, for example, take an extra day and a half or even two days off when things are less frantic.

3. Show You Care

Unfortunately, your entire team can’t take vacation at the same time—which means you’ll have the unpleasant task of needing to deny some time off requests.

When an employee’s disappointed that you’ve said no, don’t act like it’s no big deal, or assume that he should just suck it up, or behave as if his feelings are not your problem.

Put simply, eliminate the words “be professional” from your vocabulary. People have emotions. It’s part of your job as a boss to deal with them. You get paid in part for doing this emotional labor.

To help show you care, frame your “no” in a kind way. Perhaps, think about a time when you had to miss an event that was important to you and share that story with the employee. Or you could offer something else to show that you truly care. A half-day that doesn’t count against his PTO in January? A full day off? Drinks on the company? How about lunch?

A good response looks like this:

“I'm sorry, but I need you to work then. I know it sucks to have to work over the holidays. I remember a time when I [example]. If there’s something I can do to make it a little easier let me know. How about an extra day in January?”

Remember: A little compassion goes a long way.

Lastly, remember that as the leader, you should be the one to work when nobody else wants to. Not all the time. But not never or almost never either.

I know, this isn’t the most fun time of year for managers and having to decline vacation requests certainly adds a layer of stress to the holidays. But if you’re fair, kind, and flexible with your team, they can’t act like you’re insane for not wanting everything to burn down over the holidays.

This article is part of our monthly Ask an Expert series—a column dedicated to helping you tackle your biggest career concerns. Our coaches are excited to answer all of your burning questions, and you can submit one by emailing us at editor(at)themuse(dot)com and using Ask a Candid Boss in the subject line.

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