Ask Sophaya: How Do I Deal With Time Off Requests?

Dear Sophaya, 

It’s the holiday season and my entire company is in a jolly mood. Which is great, except for the fact that it also means that all of my employees are hoping to take time off of work. I’m not new to this management thing–I’ve managed in-house employees in the past–so I know how to approve holiday time-off requests. However, this past September I took over an entire remote division, and I’ve never handled remote workers’ time-off requests before. What do I need to know before I start approving or denying requests?

Happy Holidays,

Not Scrooge, I promise!

Dear Not Scrooge,

Don’t worry–there is no judgment here! Taking over an entire remote division can feel daunting, especially if you’re used to managing in-house employees. And it’s great that you’re thinking proactively about the best way to accommodate your remote workers’ holiday plans. Your anticipation of their needs is proof that you care.

You mentioned that you have experience managing in-house employees and in approving time off in general. Here is some good news: All that experience translates here, too. Although some of the parameters may feel unfamiliar, the basic principles of managing time off for remote workers are not very different from managing time off for in-house staff. 

This is what I mean: Just as you would with traditional in-house employees, you’ll want to start by studying your company’s time off policies. Before you get too deep in the weeds, start by considering your staffers’ employment type. If you are dealing with traditional nine-to-five workers who just conduct their work outside your office, you will likely be able to consult your company’s time-off policies for answers about the rules for taking time away. A human resources (HR) expert should be able to help answer questions about any holidays during which your company may be closed altogether; if there are such holidays, make sure your remote workers know well in advance that there is some holiday time available to them. 

Be aware that the rules for remote per diem or part-time workers may be slightly different; your HR expert and company policies will be able to help you understand and enforce best practice when it comes to time off for these employees.

One potential difference: If your remote workers are contractors who were brought on through an agency, they will likely have a separate set of protocols to follow. Consult with the firm(s) and employees to get a sense of what is allowed and the best way to process their time-off requests. 

Depending on the nature of your work, it might be helpful for you to know your employees’ holiday schedules in advance. If so, be sure to connect with your remote employees as soon as you can to communicate your needs. 

For example: Some managers might like their staff to share the status of projects in progress and develop coverage plans so that work can continue while they are away. Others might like a one-week notice from remote workers taking time off. Try to let your employees know the process you’d like them to follow as soon as possible so they have plenty of time to solidify their schedules and confirm them with you.

With just a little time left before the holidays, now could be a great time to create a company culture that encourages self-care and time off for remote employees. You could do this by creating a shared online calendar, for example, where employees can feel empowered to record their time off. In this way, others can feel empowered knowing that their peers are taking the time they need. As manager, you can also record your time away here to set an example that vacation is expected (and totally acceptable).

It’s worth noting that requesting time off can be especially stressful for remote workers. Even though you’re likely well aware that your staff is hard-working and devoted to your company, it can be difficult for those who are not in the office every day to feel seen. Remember– and remind your employees that you remember–that remote workers are invaluable assets to your company. 

Just like traditional employees, they should not be expected to be available 24/7, and they should be encouraged to enjoy a work-life balance. When you discuss holiday requests with your employees, be supportive about their holiday plans and encourage them to take time they deserve. 

From your note, it is apparent that you take your employees’ needs seriously. The best advice I can give you is to lead with that empathy and supportive nature, and communicate as much as possible to ensure that your needs and the needs of your team are met over the next few months. 

I hope that you and your remote employees all enjoy restful holidays. 



Featured image by Sai Kiran Anagani