How to Manage Remote Employee Time Off Requests

Time zones, asynchronous schedules, and limited face-to-face interaction make managing remote time off one of the trickiest parts of remote team management. 

When it comes to time off, you’ll need to balance maintaining employee morale, promoting fairness, and maintaining work-life balance.

Remote companies can’t settle for a generic PTO policy to achieve that. A good remote time off policy should manage workloads, prevent burnout, and protect personal time.

The stakes are high. A poorly executed system can disrupt workflows and hurt morale, but a thoughtful approach can build trust and improve employee satisfaction.

This guide will explain the key steps to managing paid time off for remote workers.

The unique challenges of managing remote time off

Managing PTO for remote employees comes with hurdles you can’t ignore.

While managing PTO for in-office workers has its fair share of challenges, remote work introduces variables like:

• Multiple time zones
• Unique holidays and cultural differences 
• Limited face-to-face interaction
• Lack of technology for visibility and accuracy of time off

If not handled properly, all of these issues can derail team collaboration, but let’s start with the time zone issues. 

Remote work and diverse time zones

A major upside to remote work is having 24/7 coverage across various time zones. Unfortunately, these time zone differences are a disadvantage regarding time off.

Time zones create complexities in planning and approving PTO, as the lack of overlap in working hours can delay decisions and impede team workflows. Key challenges remote teams face include:

• Delayed approvals. A last-minute PTO request from one time zone might not get reviewed until the next day if the manager is in another. 
  
• Coordination gaps. A global sales or support team can provide 24-7 availability — but only when everyone is available to work. It’s harder to schedule coverage when employees’ working hours don’t align.
  
• Fragmented collaboration. When team members take time off, remaining employees may struggle to complete tasks without direct support.

For remote employees, clear communication and planning entail setting specific deadlines for PTO requests and requiring backup plans for important tasks.

Maintaining team balance with limited in-person interaction

When remote team members take personal or sick days, the lack of physical presence makes it harder to assess and manage workloads. Here’s how to keep things balanced:

• Practice transparent communication. Remote work thrives on proactive updates. Make it easy for employees to share when they’ll be unavailable with managers and teammates. 
  
• Plan for coverage. Train employees in preparing handoffs. That means assigning tasks and documenting progress before taking time off so work won’t stall in their absence.
  
• Use the right tools. Use tools like scheduling and PTO tracking software to keep everyone informed about who’s out and when.

Clear workload expectations and documented processes keep the team productive and focused — even when unexpected absences happen.

Key steps to effectively manage remote time off requests

Create a clear remote time off policy

A good remote PTO policy starts by clearly defining the different types of time off available for remote employees:

• Vacation. Paid leave for employees to recharge. For companies offering unlimited vacation days, clearly define expectations for how and when this time can be used.
  
• Sick leave. Time off for physical or mental health recovery. These often do not (and should not) require detailed explanations or documentation.
  
• Paid leave for certain holidays. Allows employees to celebrate culturally significant days without worrying about their workload.
  
• Unlimited PTO policy (if applicable). Grants employees unlimited time off. This is a very powerful workplace benefit but requires high levels of trust and workload awareness. While unlimited PTO would suggest no limit to how much PTO one can take, employees obviously can’t take too much time off as they still have to work and meet job expectations. 
  
• Mental health days. Encourages employees to prioritize well-being by allowing them to take days off to decompress.

Next, you need to establish clear rules for requesting time off.

Require employees to provide advance notice for planned absences, such as two weeks for vacations. 

For emergencies or unplanned sick leave, same-day notifications are perfectly acceptable. Remote policies should accommodate employees across various time zones and cultural backgrounds.

One way to show your commitment to supporting a diverse workforce is to allow team members to take time off during regional holidays. Floating holidays are also a good option, as they give them more flexibility.

Standardize the time off request process

Standardization of policies is crucial for bringing order to any team. Without it, managing PTO days (or any process, for that matter) can become chaotic.

With a clear, consistent process for requesting time off, no staff member is left guessing, and the team keeps running smoothly — even when people are away.

You don’t need to develop anything too complicated. Start by setting up a simple request system using tools like online forms or HR software. You can also look to attendance management software to reduce the administrative burden and better track requests.

These tools make it easy for employees to log requests for paid vacation time, personal days, or other types of leave. 

Timelines for submitting and approving requests must also be clearly explained. For instance, you can require at least two weeks’ notice for planned PTO days and same-day notification for emergencies.

If a team member is going away for an extended period (e.g., two to three weeks), you might want a policy that requires them to give one month’s notice so you have more time to plan for their extended absence.

Managers should review requests promptly (ideally within 48 hours) to avoid uncertainty for the staff member making the request.

Implement fair approval guidelines

Approval guidelines for time off requests should be objective and transparent. Bias and inconsistency can lead to frustration and morale issues, so use clear criteria to evaluate every request, like:

• Submission timing. Prioritize requests based on when they’re submitted to maintain an orderly process.
  
• Workload impact. Consider how the absence will affect project timelines and other team members, especially for critical roles.
  
• Accrued PTO balance. Give preference to employees with accrued PTO that’s approaching its expiration date. More importantly, be mindful of employees who haven’t taken PTO in a while, as they may be in danger of burnout.
  
• Recent time off. Review how often a staff member has taken time off recently to balance opportunities across the team.
  
• Team coverage. Avoid overlapping absences for employees in similar roles or with interdependent tasks.

If two employees in identical critical roles request overlapping dates, evaluate workload and prior usage to determine the fairest solution. While this approach requires some compromise, it helps prevent conflict and promotes a balanced vacation policy for everyone.

Use technology for transparent scheduling

There are several tools that can help businesses track time off and give team members the ability to plan and request PTO more effectively. Here are a few great options:

• Google Calendar. A simple yet effective way to track time off, mark absences, and view team availability at a glance. Shared calendars can provide visibility into PTO, work-related travel, and more. 
  
• Hubstaff. Track time, manage PTO, and monitor hours worked with a workload management platform designed for global remote and hybrid teams. Request and approve PTO, generate timesheets in real time, and pay each team member accurately on their preferred payroll platform. 

• Slack. Keep teammates informed in real-time by setting a custom status for planned absences or hours worked outside of regular schedules. Have employees tweak notification settings while they’re out for a healthy work-life balance.
  
• BambooHR. This HR tool has a PTO tracking feature and automated approval workflows. Tools like BambooHR can reduce administrative overhead for businesses.
  
• Asana. Its calendar feature lets you visualize team schedules alongside task deadlines to help plan for tasks weeks in advance.

The tool you choose matters, but the most important thing is that everyone knows how to use it effectively.

Even the best tools fall flat if employees can’t use them correctly. Pick one that fits your team’s workflow, and make training part of the implementation process.

Encourage proactive coverage planning

The key to keeping workflows uninterrupted is preparing for absences well in advance. This starts with open communication. 

Encourage employees to inform their team members about upcoming time off as early as possible so everyone can plan accordingly. Key tasks that will need attention during their attention have to be identified so temporary ownership may be assigned to someone else. You have to trust employees to perform this process responsibly.

For example, they can create a quick handover document that includes:

• A list of tasks in progress, with each one’s current status. This could live in your team’s preferred project management system. 
• Detailed instructions and contingency plans for critical responsibilities.
• Contact information for clients or stakeholders, if relevant.
• Deadlines that must be met while they’re away.

Solid planning allows team members to take time away from work without unintentionally dragging down their team’s productivity. The fewer the surprises, the better.

Track and evaluate time off trends

Tracking time off is a game of spotting patterns.

This is a lot easier with a tool like Hubstaff, as it lets you monitor who’s taking advantage of unlimited paid time and who’s leaving unused PTO on the table. Both extremes are red flags:

• Employees who rarely take time off could be at risk of burnout
• Frequent or unplanned absences may signal other factors like workload imbalance or disengagement.

To prevent this, data should be regularly reviewed to identify trends.

For example, are requests clustering around a specific time of year? Is a particular team carrying more absences than others? 

These insights let you adjust your time-off policy to better accommodate each employee’s specific needs.

Finally, don’t stop at numbers. And don’t look at data without context. Look at the past — have employees voiced concerns about PTO fairness, scheduling conflicts, or difficulty taking time off?

Combine that feedback with your data to make sensible, meaningful policy updates that contribute to a healthy work environment.

Recognize cultural and regional differences

Managing time off for a global team means recognizing that cultural and regional differences play a significant role in expectations. Holidays, religious observances, and cultural norms can vary wildly from one employee to another. 

In other words, trying to create a one-size-fits-all policy will only lead to alienating some employees. For instance, some cultures emphasize long holiday breaks, while others prioritize shorter but more frequent time off.

Employees who work remotely across different regions may expect certain local holidays off —  even if those days aren’t recognized where your country is based. Flexible policies that allow employees to substitute company-recognized holidays with culturally relevant ones can also go a long way in building trust.

Let employees know they can openly discuss their needs for time off tied to their background or personal practices. Workplace politics should never be a factor in any scenario.

Next steps

Managing remote time off starts with structure.

Build a PTO policy that’s easy to follow and accessible to your team. Then, tools like Hubstaff or Google Calendar can be used to make schedules visible and minimize overlap.

Then, go beyond logistics. Pay attention to patterns like unused PTO or burnout, and tweak your approach to keep things balanced.

Finally, keep communicating throughout — because no amount of data will ever be more valuable than your team’s honest words.