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Holiday Scheduling: Your 6-Step Plan to Perfect Staffing and Happy Employees

The holiday shopping season presents numerous challenges and increased busyness for any retail business. One of the most critical issues? Holiday scheduling for staff.

Inventory, promotions, and sales are all top of mind for retailers across industries. But holiday schedules must be too. Why?

Because it’s personal. The holidays are a busy time for your employees outside of work. Causing them to miss too much or be overworked could mean you start the new year minus an employee or two. 

The key is to balance what your store needs for staff and what your employees need to stay happy.

We’ll discuss the importance of this balance, and how to nail your holiday employee scheduling this year. By the end of the article, you’ll have several practical ideas you can implement immediately with your team.

How to Balance Holiday Scheduling and Employee Satisfaction This Year

The holiday season between Thanksgiving and the end of the year is important for retail businesses. You can expect more foot and online traffic as people look to spoil their loved ones with gifts and vouchers. In other words, your customers are primed to spend.

That can only be a good thing, right?

Yes, but only if you manage it well. Sure, you have a big opportunity to engage new customers and further please loyal customers, but with that opportunity comes the need for more staff for checkouts, assisting customers, answering questions, gift wrapping (if you offer that), and more.

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

Without a strategy for staff scheduling, you could end up providing slow service, upsetting customers— and your sales might take a hit. You’ll also upset your staff because they’ll feel the brunt of your customers’ wrath.

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.

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

Organizing schedules early is the best way to ensure your employees are happy with holiday schedules. Blackout dates are days when you expect high traffic, and you’ll need all hands on deck. 

If employees are aware of these dates, they’ll know you need them and can make plans accordingly. Make sure you communicate with your staff as early as possible.

Typically, you’ll need more staff on Black Friday and Small Business Saturday. Then you’ll have the last-minute shoppers who decide to leave their shopping until the weekend before Christmas. You can also expect many customers will want to take advantage of sales leading up to the New Year.

The right point of sale (POS) system has historical data you can use to find out your busiest days in the last one to two years. Don’t go overboard. It’s not fair to expect everyone on your team to commit to working every holiday, so be fair on your busiest dates.

2. Communicate About Holiday Staffing Early and Often

If you communicate early with your staff that you’ll need them to take on more shifts over the holidays, it shows you’re willing to be transparent and that you care about them.

Set clear expectations. Don’t put off responding to requests. Instead, tell your staff you’ll do your best to honor requests, but accommodating them won’t always be possible. You can also set a deadline for requests to ensure your team doesn’t leave it until the last minute.

Once the schedule is set, there should be no reason for changes. But make room for shift swapping. You could offer self-scheduling options. Allow employees to check their schedules and switch shifts, giving them more control over their holiday plans. Ensure you set procedures for communicating changes promptly.

Pro tip: Only some people want time off over the holidays. Some employees don’t have big celebrations and might appreciate extra shifts.

3. Hiring Seasonal Workers? Be Clear on Scheduling Policies for Them Too

Setting clear expectations before hiring seasonal workers helps them decide if they want to move forward with seasonal employment.

It’s important to note that seasonal workers can help things run smoothly or cause conflict and upset within your team. If you’re clear that your scheduling policies extend to them, too, it shows you’re an employer with integrity.

Hiring seasonal workers is another thing you should start planning early. You still need to screen candidates to see their previous experience and how much training they need. Did they follow instructions well on their application? Are they interested in the role, or just looking for extra work?

Training and onboarding play a big part in the success of seasonal staff hires. Ensure they have early access to product resources, training guides, and branding materials.

Related: 5 POS Training Tips to Help Your Workforce Successfully Onboard

You could also team new hires with veteran employees who can provide support. This helps both sets of employees feel valued and that you’re invested in their success.

4. Employee Rewards

If you’ve worked up the retail ladder, you know what it’s like to work during the holiday period. Employees must deal with customers quickly, process returns, and potentially miss family celebrations. And they have to do it with a smile. If you appreciate your employees, show them.

Check in with your team and ask them what they need to have a successful holiday working experience. The more you support your team, the more likely they will stick around and pull together to help your store succeed.

Offering employee rewards year-round will incentivize them to pick up shifts when you need them to. You can:

  • Offer discounts on merchandise or early access to sales items.
  • Offer a gift card to their favorite restaurant.
  • Implement a rewards platform to enable employees to choose their rewards.
  • Give employees you trust more responsibility so they feel valued.
  • Build a culture of recognition: gather employees at the end of the day and verbally recognize their efforts, give employee-of-the-month rewards, and encourage peer-to-peer recognition.
  • Surprise employees by letting them go home early on successful days, or take your team out for a meal to celebrate successful holiday periods.

The idea is to motivate employees to want to work for you — to want to help out when you need them the most. It also helps seasonal staff see that your store is a great place to work.

5. Assign Work Responsibilities and Cross-Train as Needed

Because the holiday period is busier, you might need staff to step up and take on tasks they haven’t done before. If you have employees who handle specific tasks and take time off, you don’t want that responsibility to fall on you.

Delegating responsibility is one way to boost morale and employee engagement. For example, asking one of your team to close out tills shows you trust them with sensitive tasks.

How can you ensure tasks critical to your operations are done correctly, even if you’re down a few employees? Cross-training.

Cross-train employees on everything from inventory and working the cash register to greeting customers and production (if you produce some of your own goods). An added benefit is that you might find an employee who excels in one area. They might also enjoy working in that area, and you have a win-win.

6. Use a Scheduling Tool to Make Things Easier for Yourself

We’ve seen retail store owners from local goods and markets to liquor stores and tobacco shops try to manage employee schedules manually. If you have a small team, it’s more manageable, but it’s still taking up time you could spend driving growth in your business.

Spreadsheets and Microsoft Word documents are not fun to work with, and mistakes are easy to make. And employees can’t quickly see what their schedule is like because there’s no dashboard.

An employee scheduling tool solves these issues. Several are available, and you’ll need to find one that fits your needs. From scheduling conflicts to staff availability time-off requests, you should be able to manage it all with the right scheduling software.

It’s even better if your POS system can do it all. With employee management software integrated into your POS system, there’s one less tool to purchase, learn to use, and manage.

Holiday Scheduling to Employee Timecards: Your POS Can Assist With It All

Employees are a core part of your store’s success during the holiday season. There’s no point investing in marketing to bring more people into your store if you can’t serve them well. 

You might think it’s impossible to staff your store during the holidays and keep your employees happy. But the tips above will help you make better decisions and still help your staff to enjoy working at your store and under your management the whole year through.

It’s easier to manage all aspects of your staff with POS Nation’s software:

  • Schedule your team weeks in advance to ensure you have proper coverage, especially during the holiday period.
  • Set permissions as you cross-train and give more responsibility to staff in a few clicks.
  • Add, onboard, and train seasonal staff.

Discover how our POS can positively impact your business by scheduling a demo with one of our team members!


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Lynn Ellison

“POS Nation saved us about 30% on our credit card processing fees.”

Lynn Ellison, Owner Liquor Stop

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