How to Manage Employees’ Holiday Schedules Without Going Nuts

How to Manage Employees’ Holiday Schedules Without Going Nuts
Holiday scheduling and staffing made easy. Top holiday scheduling tips for small business owners, including managing expectations and minimizing stress.
by Kaitlin Keefer Aug 09, 2023 — 2 min read
How to Manage Employees’ Holiday Schedules Without Going Nuts

Staying sane throughout the holidays is tough enough as a small business owner. And with employees, you have the added stress of managing their time off during your busiest time of year. But holiday scheduling and staffing doesn’t have to be a constant source of stress from now until New Year’s.

Follow our advice and this season you can focus on sales, not schedules.

Set an early deadline for vacation requests.

The best way to avoid scheduling stress is to finalize the calendar as far in advance as possible. Instead of putting together the schedule on a first-come, first-served basis, set a deadline for all employees to get their time-off requests in. That way you can create your holiday schedule all at once rather than piecemeal, saving you time in the long run.

Make it clear to employees that they need to get their requests in by the deadline and that once the schedule is set, it’s set. It’s up to you whether you want to allow staff to swap shifts with each other, but if you do, let them know it’s their responsibility to make sure their shifts are covered.

(And make sure that you’re using payroll software that can help you track paid time off and sick days.)

Create blackout dates.

If there are certain days and shifts when you need all hands on deck, communicate that to your staff as early as possible — before employee time-off requests are due. If you’re upfront about your scheduling expectations from the beginning, you can avoid difficult conversations later.

Get employee scheduling software.

Employee scheduling software can be a lifesaver this holiday season. These tools, such as Square Shifts, allow you to manage your shift calendars, track hours, and schedule your team from anywhere. If you use Square for your payroll software, you can sync timecards and automatically import their hours, so you can easily run payroll.

Split up responsibilities.

Once you have a schedule in place, figure out what sort of coverage you need. If there’s only one employee who knows how to do a certain task, make sure they’ve trained others on how to handle it well before their days off.

Make scheduling policies clear before hiring seasonal employees.

When you’re interviewing temporary workers to help out during the holidays, be up front with them about what you expect time-wise. If they aren’t available when you need them the most, move on to the next candidate. The whole point of hiring seasonal employees is to make your business run more smoothly, so don’t bring on people who are just going to add to your stress.

Allow employees to work from home.

If your business doesn’t depend entirely on having employees on the premises, offer a remote work option. Your staff will appreciate the flexibility to do things like run errands during the day or work from another city, and you can continue to keep things humming during a busy time.

Incentivize staff to work less desirable shifts.

It’s the holidays — there are certain days everyone wants off. To make sure you aren’t short staffed when you need help the most (say, if you’re a pie shop and it’s the day before Thanksgiving), incentivize your employees to take those shifts by offering to pay them more for those hours. You could also dangle the carrot of extra time off next year, or other attractive bonuses.

Learn more about how businesses scale their teams with Square Shifts here.

Photo credit: “Ciurila” by Cristian Bortes, Flickr, license CC by 2.0, cropped and retouched from original

Kaitlin Keefer
Kaitlin Keefer is a content strategist at Square who has covered how businesses connect with their customers and ways they can leverage tools and data to become industry leaders.


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