Your first holiday season as a business owner is exciting — and stressful. Customers flood in, employees want time off, and you’re not quite sure how to handle it all. Scheduling your first holiday season doesn’t have to be chaotic if you plan ahead.
Here’s your step-by-step guide.
Start Planning Early
The biggest mistake new business owners make during the holidays is waiting too long to plan. Here’s your timeline:
8 weeks before (early October for November/December):
- Collect holiday availability from all employees
- Review last year’s sales data (or industry benchmarks if you’re brand new)
- Identify which days you’ll be open and your holiday hours
6 weeks before:
- Build tentative holiday schedules for key weeks
- Post your holiday time-off policy
- Start hiring seasonal staff if needed
4 weeks before:
- Finalize and publish holiday schedules
- Confirm all shifts are covered
- Train any new seasonal hires
1 week before each holiday:
- Send schedule reminders
- Confirm everyone knows their shifts
- Have backup plans for potential call-offs
Setting a Fair Holiday Time-Off Policy
This is the hardest part. Everyone wants Thanksgiving and Christmas off. You can’t give it to everyone. Here are fair approaches:
The “Pick One” System
Every employee chooses one major holiday to have off. If they take Thanksgiving, they work Christmas. Next year, they get the opposite. This is simple and clearly fair.
First-Come-First-Served
Time-off requests are approved in the order received. This rewards employees who plan ahead but can feel unfair to those with less predictable lives.
Rotating Priority
Employees take turns having priority for holiday requests. If you had first pick last year, you’re last this year. Keep a written record.
Whatever You Choose, Write It Down
Post your holiday policy before requests start coming in. “The rules are whatever I decide” builds resentment. A clear, written policy builds trust — even when someone doesn’t get their first choice.
Scheduling Your First Holiday Season: Week by Week
Thanksgiving Week
- Most businesses see changes starting Wednesday afternoon
- Staff light on Thanksgiving Day (if open) with volunteers or premium pay
- Black Friday may need maximum staffing (retail) or could be slow (service businesses)
- Saturday and Sunday return to near-normal
Christmas Week
- Traffic patterns shift unpredictably — track daily
- Christmas Eve may need adjusted hours
- Christmas Day — decide early if you’re open or closed
- Days between Christmas and New Year’s are often slow — lean staffing
New Year’s Week
- New Year’s Eve may need extended hours or special event staffing
- New Year’s Day is typically slow
- The rest of the week depends on your industry
Should You Hire Seasonal Help?
Ask yourself:
- Will holiday volume exceed what my current team can handle?
- Are multiple employees requesting the same days off?
- Am I personally covering too many shifts?
If yes to two or more, hire 1-2 seasonal workers. Start the hiring process 6 weeks out — training takes time.
For more on scaling your workforce up, read our guide on seasonal staffing strategies.
Communication Is Everything
During the holidays, over-communicate:
- Publish the schedule early — 2 weeks minimum for holiday weeks
- Confirm shifts individually — don’t just post it and hope everyone checks
- Share via a tool that’s accessible 24/7 — MyCrewBoard lets employees check their schedule from any phone, anytime
- Have a call-off protocol — who do they contact, and how much notice is required?
Frequently Asked Questions
When should I start planning my holiday schedule?
Start at least 6-8 weeks before the holiday season. Collect employee availability for November and December by early October so you have time to identify and fill gaps.
Should I require employees to work on holidays?
Be upfront about holiday expectations during hiring. Many businesses require all staff to work at least one major holiday but let employees choose which one.
How do I handle multiple time-off requests for the same holiday?
Use a first-come-first-served system or rotate holidays year over year. Whatever method you choose, communicate it clearly before requests start coming in.
Do I need to hire seasonal staff for the holidays?
If your business volume increases by more than 30% during the holidays and your current team can’t cover the hours, yes. Start hiring at least 4-6 weeks before you need them.
New to scheduling? Start with our complete guide on setting up employee scheduling for your new business or learn about handling your first scheduling conflict.