The holidays mean different things to different teams.
For employers managing remote workers across borders, it means making sure nothing falls through the cracks when half your team is celebrating with family while the other half is still online.
The real problem isn’t the holidays themselves. Someone goes on leave without updating their task list. Payment deadlines get missed because nobody approves the invoices.
Remote work requires more intentional planning than you expect. You can’t walk over to someone’s desk to ask. Here’s what you can do before the holiday season
Review and Approve PTO Requests Two Weeks Before Holidays
Start this process at least two weeks before the holiday period begins. Review all pending leave requests first. Approve or deny them based on operational needs, then immediately process any outstanding payroll adjustments.
Define What Qualifies as a Holiday Leave Interruption
Sometimes emergencies happen and you need to reach someone who’s supposed to be offline. Have a plan for this before it becomes necessary.
Define what qualifies as an emergency worthy of interrupting someone’s time off. A major client threatening to leave is different from a routine question that can wait. Write down specific criteria so everyone understands the threshold.
Create a Team Absence Calendar with Time Zones
Document who will be offline and when. Create a master calendar showing exact dates for each team member’s absence. Include time zones if you’re managing workers across multiple countries.
Process International Payroll Early to Avoid Holiday Delays
Process payroll early if your regular pay date falls during the holiday period. Most international payment platforms experience delays during major holidays. Running payroll three to five days early prevents payment delays thus keeping everyone happy.
Assign Backups to Cover Each Responsibility
Name another person who will handle each task, confirm they understand what’s required, and give them access to necessary tools before the original person goes offline.
Alternative work arrangements and remote work guidelines from DTI and DOLE emphasize the importance of alternate contacts and clear delegation procedures.
Set Up Emergency Contacts Outside of Email
Create an emergency contact list with personal phone numbers or messaging apps. Email doesn’t work when someone’s truly offline. WhatsApp, Viber, or SMS might be your only option if something urgent comes up.
Inform Your Clients at Least One Week Early
As a simple matter of respect, send client notifications at least one week before the holiday period begins. Explain who will be unavailable (if not all your team members), who will be covering their responsibilities, and how to reach the backup person. .
Set Up Auto-Responders with Coverage Contact Information
Update auto-responders with accurate information. Generic “I’m out of the office” messages frustrate clients. Better versions explain when you’ll return, who to contact for urgent matters, and what kind of delay to expect for non-urgent requests.
Post Holiday Coverage Schedules in Shared Team Channels
Post coverage schedules in shared team channels or project management tools. Everyone should know who’s responsible for what during the holiday period. This prevents tasks from being duplicated or forgotten.
Schedule Quick Handoff Calls Before Team Members Go Offline
For client-facing roles, consider scheduling a brief handoff call before someone goes offline. Five minutes of direct conversation often prevents hours of confusion later.
Secure Your Systems During Holiday Coverage
Require multi-factor authentication for all business-critical systems. Restrict access to sensitive client data unless absolutely necessary for coverage. Someone filling in for a holiday doesn’t automatically need access to everything the original person could see.
Grant the minimum access required to complete assigned tasks.
Compensate Team Members for Interrupted Time Off
Compensate team members fairly if their holiday gets interrupted. Philippine labor law and international best practices both recognize that working during scheduled time off deserves additional compensation although it is different when working with independent contractors.
This isn’t just about legal compliance, it’s about maintaining trust.
Build a Handoff System That Works All Year
The best time to build a handoff process is before you need one. Teams that only think about coverage during major holidays struggle every time someone takes unexpected leave.
Create standard handoff templates your team can use year-round. Include sections for task status, system access, client information, and deadlines. Update the template based on what works and what doesn’t after each handoff cycle.
Build documentation habits into regular work routines. Teams that keep good notes all the time have easier handoffs during holidays.
Schedule regular coverage drills outside of holiday periods. Have team members swap responsibilities for a day or two as practice.
This reveals gaps in your documentation and trains people to handle backup duties before the stakes are high.
Review what went wrong after each holiday period. Talk to both the people who went on leave and the people who covered for them. Use their feedback to improve your process for next time.
Start building your handoff checklist now, even if the next holiday is months away. Each successful handoff makes the next one easier.