How To Encourage Holiday PTO Without Leaving Your Business Short-Staffed

As we enter the holiday season, many are ready to set their “out of office” messages and relax and recharge. It’s important for employers to encourage this work-life balance and promote the use of paid time off around the holidays. However, if everyone takes off at the same time, it may leave you with a skeleton crew and piles of work for when employees return, making for a not-so-happy start to the new year. 

To address this problem, we asked eight members of Young Entrepreneur Council for their own creative solutions. Below, they discuss how to strike a balance between encouraging your team to take time off and having enough available staff during the holiday season. Here’s what they suggest.

1. Ask For PTO Requests Early

We have our team request holidays off by the start of September. We believe that this gives us the time we need to sort through everyone’s requests and make a plan that works for upper management and our employees. There is less stress all around, and team members can get the time off they need. – Chris Christoff, MonsterInsights

2. Have Systems In Place For Taking Over Essential Work

When the essential work tasks are documented and automated, employees taking time off won’t result in a backlog of work. Each employee should know what their essential tasks are and who is trained to cover them. When vacation is over, be sure to assess what tasks need catching up on and if any systems updates are needed. You should be prepared for employees taking time off! – Kelly Azevedo, She’s Got Systems

3. Hire Extra Holiday Staff

One way to handle this problem is to hire extra staff for the holidays to cover for employees who are going on vacation. This takes some planning, as you have to make sure you find people who can fill in the gaps. You may be able to find employees through temp agencies. If the work can be done remotely, it’s easier, as you can find many agencies that provide outsourcing for all kinds of tasks. – Kalin Kassabov, ProTexting


4. Dedicate Special Time To Finishing Projects

Do what you can to frontload your company’s “crunch time” before the holidays. Every company should encourage their team to take time off around the holidays, but if you let work pile on in the weeks leading up to them then you’ll set yourself up for a painful bottleneck afterward. So, dedicate a 4-week period before the holidays to finishing project deadlines so you can enjoy your time off. – Amine Rahal, IronMonk Solutions

5. Purposely Stagger Vacations

Something that helps prevent a work pileup around the holidays is staggering out vacations. Because some team members are willing to put in more work around the holidays, I encourage them to relax and take time off at different times of the year, like in the summer. This way, we’re never completely unstaffed but everyone gets to take a break. – Bryce Welker, Beat The CPA

6. Close The Whole Office

I made the policy to close our office from mid-December to early January so our team can spend time with their families, take vacations or relax during the holidays. This has worked particularly well because most of our team come back to work feeling energized and recharged. – Kristin Kimberly Marquet, Marquet Media, LLC

7. Develop Employee ‘Pods’

We have adopted the concept of a pod where team members are supported with backup by their fellow pod members. This is not only great for each employee, but also a relief for the client who doesn’t want to be concerned that work is going to stop because their primary point of contact just took a vacation. – Russell Benaroya, Stride Services

8. Invest In The Right Tools To Keep Work Going

An important thing that any business should do is invest in the right tools. In cases where you can’t have everyone take time off at the same time, you can offer people flexible time and longer work-from-home options or the option to use it at a future time. You need to back this up with mobile and desktop tools that let them work on the go. – Syed Balkhi, WPBeginner

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