How to manage your team’s holiday break

Employee leave, Holiday break,

Every year, as we leave Halloween behind, employees start fantasizing about eggnog and gingerbread cookies. They dream of chilly mornings by the fire and perfectly sweet hot cocoa. You know what they don’t dream of? A frantic manager or client checking in on the status of a project.

Fortunately, you can prevent last-minute scares, meet deadlines, keep projects on track, and truly enjoy time off by planning in advance for your team’s holidays.

8 tactics for managing your team’s holiday break

Create or review your annual leave policy

An annual leave policy, aka a holiday policy, is the set of guidelines your organization follows when it comes to employees’ leave.

Your annual leave policy should include details like:

  • How much time each employee gets every year.
  • Whether there are special considerations for religious holidays.
  • If there are any company-wide days off — or days no one can take off.
  • How do you prioritize leave requests?

About this last point, there are three main strategies you can use to approve employees’ time off requests:

  • First come, first serve. Using this approach, the first person who requests time off is the one who gets it. This is simple and encourages people to book their time as early as possible.
  • Seniority. If you use seniority as a ranking factor for leave requests, more senior members get the first pick when scheduling their time off. This works well if different team members can cover for each other and their higher-ups.
  • Tenure. The third most common method to approve leave requests is by giving the first pick to employees who’ve been with the company the longest. This approach can be effective for companies where employees get additional days off every year they stay with the team.

If you don’t have an annual leave policy yet, work with your HR department and management to put one together. It’ll come in handy for all major holiday breaks.

Consider each team member’s schedule

If you work with a remote team, holiday breaks may look different for everyone. Canada vs. the US’s Thanksgiving is a great example. Similarly, people from other countries may not celebrate Christmas or the New Year but have other holidays instead.

In order for staggered time off to work, employees need to share their plans as early in advance as possible, so you’ll know who’s around and who’s not. And play off of each of your team’s vacations by having them cover for each other as time and responsibilities align. Ie, if one person is taking Christmas off but has no plans for New Year’s, have them cover for the person whose schedule is opposite.

Whenever possible, stagger vacation time so that there’s always someone around. Use your project’s dependencies to organize who goes out when — or, if possible, plan your deadlines and deliverables around your employees’ time off.


Some business functions simply can’t stop regardless of the time of year. But that’s not the case for others.

Leave “nice-to-do” work until after the holiday break and focus this time on truly essential matters. For example, keep up customer support and client services to handle the uptick in requests, but consider postponing new initiatives until January so you can better allocate your team’s bandwidth.

Have a backup plan

Even with all the plans in the world, you may need more hands on deck. One way to work around your staff’s absence is by hiring contractors or part-time help for those tasks you can’t postpone, or to complete urgent projects.

Consider going hybrid

Your employees deserve to have true time off without interruptions or fires to put out. But implementing a hybrid model can allow them to enjoy more time with family without actually having to use PTO.

If there are already going to be fewer people at the office, consider offering a WFH setup over the holiday break for those who are on the clock.

Plan for interruptions

While you may be able to stick to a semi-regular schedule and keep projects rolling over the holidays, it’s normal for delays to happen.

It’s unrealistic to think that you’ll be able to complete everything perfectly on time over the holidays. So, if possible, try to align more hands-off tasks, such as reviews and updates, with this period instead of scheduling deadlines for more labor-intensive parts of the project or those that require meetings.

Do what you can in advance

It’s a good idea to devote some of your resources in the months leading up to the holiday break to preparing as much as possible in advance. A few things you can do early on:

  • Inventory/new orders. Especially with supply chain delays, you’ll want to stock up on anything you need for the holidays as soon as possible — or risk going without.
  • Holiday marketing. Did you know that many product-based businesses start preparing holiday marketing campaigns as early as Q2?
  • Bookkeeping. You can’t file taxes in advance. But you can keep your books in order, especially as the holidays often mean extra sales — and expenses.
  • Planning. Do you send holiday gifts to clients or employees? Find suppliers early on to get the best prices and plenty of choices.

Share your plans with all of your stakeholders

Your team isn’t the only one going on a holiday break. Chances are many of your stakeholders are, too. Save everyone some stress by reaching out with your team’s plans and asking about theirs so that you can schedule milestones appropriately.

Planning for the holidays in advance helps keep everyone aligned and able to deliver on time. Plus, it’ll keep everyone’s stress at bay and clients feeling supported throughout the holidays.

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