Holiday Scheduling: 7 Steps to Perfect Staffing and Happy Employees

If you manage a small retail team, one missed shift can throw off your entire day. 

That gets even harder during the holiday rush, one of the busiest times of the year for most businesses, because your team likely requests days off when you need them most.

Overlapping time off can leave just one or two people handling the store’s entire operations. A good holiday schedule should spread the work across your entire team so no one carries the whole store alone.

In this blog, we'll cover seven staffing tips for a more organized holiday schedule, from using last year’s point of sale (POS) data to hiring seasonal help.

How To Balance Holiday Scheduling and Employee Satisfaction This Year

The holiday season, spanning from Thanksgiving to the end of the year, is crucial for retail businesses. Seasonal traffic, both in-person and online, can bring in more sales as folks shop for their loved ones.

And that’s great news, as long as you manage scheduling well. More customers means more staff to answer questions, manage checkout, and handle gift wrapping (if you offer that service).

You don’t want holiday schedules to become a source of friction in your business. Let’s look at how you can ensure your customers and staff are happy during the holiday season.

Related Read: 6 Retail Checkout Counter Ideas for Higher Sales & Happier Customers

1. Pull Last Year’s POS Data To See Peak Hours

As a frame of reference for this year’s staffing needs, start your holiday scheduling with last year’s numbers. Your POS system records every sale, so you can see which days and times drew the biggest crowds.

Here’s how you can analyze historical sales for holiday staffing:

• Pull sales by day. Run last November and December sales by day in your POS reports, and mark your five busiest days.
• Break busy days into hours. Find the hours when sales spiked since those hours need your strongest coverage.
• Compare sales to timesheets. Check who clocked in during each spike. Hours with high sales and few people on the clock show where you fell short last year.
• Mark your slow stretches. Quiet hours give you room to approve time-off requests, schedule training, or send people home early, if needed.
• Adjust for this year. Add anything that’s changed since last year, such as a new promotion or longer store hours, and plan extra coverage for those windows.

For example, let’s say last December’s reports show the heaviest traffic on the weekend before Christmas, around 3–5 p.m. In that case, you’d want to schedule your most experienced register staff for those hours, and keep newer hires on lighter morning shifts.

Pro tip: Your top days often land right before a holiday — typically December 22–24 for liquor stores, or the weekend before Christmas for groceries.

2. Set “Blackout” Dates on the Time-Off Calendar

Creating schedules early is the best way to keep your employees happy with their holiday hours. Blackout dates are days when you expect high traffic and need all hands on deck, and it’s important to share those times with staff as early as possible.

As mentioned in the section above, POS data can help you identify these peak times — but many stores find they need additional staff on Black Friday and Small Business Saturday.

Here’s how to keep blackout dates fair for your team:

• Pair blackout dates with a daily cap. Block your peak days entirely. On every other day, limit how many people can take time off and approve requests first come, first served.
• Rotate who gets the most requested days. If the same few people file requests months ahead, they get the same holidays off every year. A yearly rotation, a seniority tiebreaker, or both keeps it fair.
• Determine your call-out policy. Capping time off can lead some people to call out sick instead. Write down how you handle unexcused absences so the rule applies to every kind of absence.

Having your whole team available is ideal, but not everyone can work every holiday. Keep expectations reasonable, and lock in the schedule as soon as you know your busiest dates so everyone can plan around it.

3. Communicate Holiday Schedules Clearly

To keep a line of communication open with your staff, set a clear timeline for when they can put in time-off requests and when the finished schedule will go out.

Aim to collect requests four to six weeks before the busy stretch, then share the finished schedule at least two weeks ahead.

A staff meeting can help here, especially for new and seasonal employees. People can ask questions and volunteer for hard-to-fill days like Christmas Eve, and an email or text afterward puts the dates and deadlines in writing.

When it comes to shift swaps, store owners ultimately make their own rules, but a few ground rules help. For example, require the swap partner to already be trained on the same tasks and the requesting staff member to have written manager approval before the swap is official.

Apply these rules the same way for every employee, and keep in mind that late changes to a posted schedule can trigger extra pay in places with predictive scheduling laws.

Related Read: 9 Retail Management Strategies To Implement Today

4. Plan Seasonal Staff Headcount and Onboarding Early

Many folks look for temporary work around the holiday season, which makes it a good time to bring on extra help.

But first, you need to figure out just how many people you’ll need — and that, just like the first tip, requires POS data.

Last year’s busiest periods show where seasonal hires help most. Weighing their wages plus training time against the sales from those hours gives you a realistic idea of what you can afford.

Starting new hires a few days before traffic really starts to flow in gives them time to learn your store and practice alongside a veteran employee. A solid training and onboarding process makes that time count.

Bonus Resource: How To Build a Reliable Retail Team in a High-Turnover Industry

5. Reward Employees for Holiday Shifts

If you’ve worked up the retail ladder, you know it’s not always easy to work during the holidays. Employees handle an influx of customers and lots of returns, and they may miss family celebrations along the way.

If you want your team to feel less hesitant about working those days, they need a compelling reason to say yes — and paying them more is one of the most direct ways to be fair.

Related Read: How To Reward Grocery Employees Without Spending a Fortune

Some small business owners pay time and a half for holiday shifts, but it’s worth checking your state and local rules on holiday and overtime pay before you decide.

A pay bump might not fit every budget, so here are other ways to show you value the extra effort:

• Offer first pick of hours. Give the staff who cover your peak days first choice of shifts in slower weeks.
• Give merchandise perks. Provide discounts on merchandise or early access to sale items.
• Send a gift card. Offer employees a gift card to a favorite local restaurant or business to show you value those extra shifts.
• Reward a strong stretch. Let people head home early after a strong day, or offer free meals for those working a busy stretch.

Whatever you choose, it works best when applied the same way to every employee, and your team should know about it before the season starts. Asking what would make holiday shifts easier for them also helps you choose rewards they care about.

6. Assign Work Responsibilities and Cross-Train as Needed

Holiday coverage gets thin fast when only one person knows how to do each job.

Cross-training fixes that by letting several people handle each task, from sorting inventory and working the cash register to greeting customers and managing production (if you make some of your own goods).

Start with the tasks only one employee currently handles. A newer employee can shadow the veteran, then try the job for themselves and get feedback.

Handing a trusted employee extra responsibility, like closing out tills, shows you trust them with sensitive tasks. A quick check-in the first few times gives them a chance to ask questions and ensures they’re training correctly.

POS systems can make work assignments even easier. In many of the systems offered by POS Nation, role-based permissions let you control register and drawer access for each employee, including the seasonal ones.

7. Use a Scheduling Tool for Better Organization

Schedules change on the holidays more than other times of the year. Requests pile up and swaps happen late, which makes a spreadsheet or Word document hard to keep current, and employees have no dashboard to check their own schedule.

An employee scheduling tool puts availability and time-off requests in one place, so you can spot conflicts before you post the schedule. Many also let staff view schedules and request swaps themselves, which saves you from handling every change one message at a time.

A scheduling tool handles the schedule itself, and your POS supplies the data behind it. Sales reports show your busiest days and hours, so you can schedule around real traffic, and a time clock lets staff clock in and out at the register for payroll timesheets.

Some POS systems let you set up task reminders for nightly cleanup or cooler restocking, helping routine work stay on track when the store is busy.

Holiday Scheduling to Employee Timecards: How POS Software Helps

Employees are a core part of your store’s success during the holiday season, and it can feel challenging to keep everyone happy and productive the entire time.

The seven tips above can help you make better decisions and make sure your staff enjoys working at your store, and under your management, all year long.

Every store runs differently, so the right POS for yours depends on how you schedule, report, and manage your team. POS Nation can help you find your match. Schedule a demo with one of our retail experts to see which features fit.

And remember: Staffing is just one part of holiday prep. POS Nation is proud to promote Small Business Season, which shares business tips for small retailers heading into the holidays, so you can get the rest of your store ready, too.