Managing Time Off When Everyone Wants Holidays

The challenge? Balancing fairness, morale, and legal compliance—especially if you’re managing a tight team.

Holiday scheduling conflicts aren’t just about who gets the time off. They can create resentment among employees, disrupt operations, and—if handled poorly—lead to wage and hour violations. Whether you’re closing for a few days or staying open during peak shopping season, a clear, consistent policy is key to keeping both your team and your business protected.

Understanding the Legal and Practical Balancing Act

Holiday scheduling decisions often touch multiple areas of employment law, including wage, hour, and discrimination rules. While you’re not required to give paid holidays (unless stated in a contract or policy), how you handle requests still matters.

If you approve time off inconsistently, it could raise fairness or bias concerns. If you require employees to work longer hours, you must follow federal and state overtime laws, even if they volunteer for extra shifts. And if you hire seasonal workers, you’ll need to ensure they’re properly classified and paid.

To avoid issues:

• Communicate time-off rules early in the season.
• Review your policy to make sure it applies equally to all employees.
• Track hours carefully—especially for nonexempt workers who may earn overtime.

Fairness and consistency aren’t just good for morale—they’re your best legal defense.

Smart Scheduling Strategies for Small Teams

With fewer employees, flexibility is your biggest asset. Start by staggering schedules or offering partial-day shifts to share the load. Cross-train employees so more people can fill in when others are off.

Some business owners find success using incentives—like holiday bonuses or future time-off credits—for those who work unpopular shifts. You can also encourage employees to plan time off early and use a “first come, first served” system or a rotation to ensure fairness across years.

Even if you can’t give everyone what they want, showing transparency and effort can go a long way toward keeping morale up.

Questions SMBs Should Be Asking Before Making The Holiday Schedule

Before approving or denying requests, ask yourself—and your management team—a few key questions:

• Do I have a written time-off policy that protects me? If not, how can I document decisions to avoid claims of favoritism or discrimination?
• Am I complying with wage and hour laws? Are my overtime and scheduling practices legal and properly recorded?
• Have I applied the same standards to everyone? Could an employee reasonably claim unfair treatment based on how I handled prior requests?
• Is my scheduling process clear to the team? Does everyone know when and how to request time off—and what happens if too many people do?

What to Do Next

To keep your business running smoothly through the holidays:

1. Review and update your holiday policy to include how requests are prioritized and how much notice is required.
2. Communicate early and in writing—ideally before November—to avoid last-minute conflicts.
3. Track hours and pay carefully, especially for hourly or part-time workers who may hit overtime thresholds.
4. Use a simple scheduling tool or ask Rocket Copilot to help draft a compliant time-off policy.

Good planning now keeps the peace later. Set clear expectations, follow the rules, and your business—and your team—can enjoy a happier, smoother holiday season.