Keep Your Business Running Smoothly through the Festive Holiday Season

While there’s a lot of fun that comes with the festive and holiday season, there can be plenty of stress too. Managing a business has a lot of responsibilities all throughout the year, but with the added duties of promoting yourself for the holidays, plus just personally dealing with it all, this season can be a lot.


In my own businesses and those I’ve helped as a consultant, I’ve seen how easy it is to get overwhelmed around this time. So I’m here to help with a little guide to make your season just a little bit easier. It’s never too soon to start making a plan and looking over strategies that help keep things running smoothly.


We also asked sellers like you what their businesses do for the festive/holiday season, and featured some of their suggestions here, including how to manage orders, take your business online, manage long lines, and stay fully staffed.  



@Twiggy, from TWIG Michael Pooley Flowers, breaks out the red rope to handle long lines.


Be Prepared with Pre-Orders

When it comes to holidays, planning ahead is key both for your customers and for your business. They don’t want to get stuck without what they need, and you don’t want to get stuck without inventory or scrambling to fill orders at the last minute.


You can start taking pre-orders a long time in advance to lock in sales early and to know what to expect. Especially if you’re selling items that you have to make or order, having an accurate count ahead of time is key. @phillipsrw, from CoCoChemistry, says “We offer pre-orders for some of our items like Advent Calendars during July … which is great as we can get a more accurate handle on print quantities.” 


Setting up and preparing an eCommerce website to accept these orders in the background prevents you from spending extra time and effort to track and remember them. Square Online syncs to your Item Library, POS, and Orders applet, so all of your orders and inventory data are in one place. 


@PartyManiaMD, owner of Party Mania Bethesda, is trying out Square Online this year, in a novel way. He says, “this will be our first trial run using Square’s online platform to sell costumes online only … giving me a lot more shelf space … I plan on getting 1-2 iPads on stands for people to look at costumes we have in stock through our website. Before we had to dedicate twice as much space for half as many costumes.” It’s an innovative system to offer a digital catalog for their customers, both in-store and online, and to free up shelf space for other items and employees for other tasks.



New Square Tap to Pay on iPhone in the U.S. lets you take payments without extra hardware.


Manage Long Lines

If your business gets long lines, sometimes you need some good old fashioned queuing techniques. @Twiggy, from TWIG Michael Pooley Flowers, breaks out stanchions and red rope to help guide their customers, keep them organized, and prevent them from blocking traffic on the sidewalk. You could also use tape or paint on the ground to mark out the rows, which is a bit lower profile but isn’t always seen. 


If you have limited space inside but your customers know what they want, one of my favorite techniques is line busting. You can give some of your employees portable POS devices, like a phone or Square Terminal, that they can use to walk down the line and take orders and payments right where they are. This cuts down on the amount of time your customers are waiting just to order, and lowers the stress levels of your employees too.


🇺🇸 U.S. sellers only: Another great way to reduce long lines is to utilize contactless payments. With the new Square Tap to Pay on iPhone, you can take contactless payments right on your iPhone, from debit or credit cards and mobile devices, without any extra hardware.


Stay Fully Staffed

The holidays are a time for family, and your employees have families too. So staying fully staffed and keeping your business running during this time can be an issue. It’s important to start thinking about this early and to set expectations. 


First, you have to know what you’re dealing with. If it’s not your first year in business, look back at the data from previous years to see how busy it was throughout this time. From there, you can determine and decide how many employees you will need per shift.


Communication is key, and having open conversations with your staff will help you guide your strategy. Find out what their plans are, who is willing to work on which days, and which are absolute noes. Based on these conversations and your staffing needs, you may decide to set a policy limiting which and how many employees can take off during that time. Decide what your business hours and policies will be, then communicate that to your team. 


@Lovewell, from Lovewell Tea & Coffee, talks about their system, “We don’t have any huge problem with time-off requests. We do have some blackout dates through December that are pretty non-negotiable (unless for serious reasons) and that hasn’t been a problem for us because we close our shop for Christmas through the end of the year to give our team time off with family and friends and just enjoy the holiday!” This sounds like a great middle ground to have all of their employees work on the busiest days, and then close up shop and give time off on the actual holidays.


It can be a bit complicated to make sure your employees all know their working schedule and to keep track of their time-off requests. To make things easier and have it all in one place, you can use a digital scheduling system, like Shift Scheduling with Square Team Management, to set up your employees’ schedules and have them request their time off. This updates in real time and can send a notification to your team when you make changes, so they’re always informed.


Slow? Go Seasonal

While this can be an extremely busy season for some sellers, it’s the slowest time of year for others. You may decide that staying open isn’t worth it, and closing up shop may be the best course of action if staffing is extremely limited or your sales are too low. It’s a big decision to make, so think it through and read up all about it.


Have Fun

Holidays can be stressful times to be a human in general, on top of all of the other stresses of owning a business. No matter what you do, try to enjoy the festive spirit and have some fun along the way. 


See More Articles in this Series:


Do you have any extra tips to share? Leave your best strategies in the comments, along with some pictures or videos of your holiday set up! 

Aylon Pesso is a former small business owner, consultant, and Square Super Seller, in New York. As Squares Small Business Evangelist, Pesso works to understand and assist sellers’ business needs, including creating and running the Square Readers Book Club.


This article is for educational purposes and does not constitute legal, financial, or tax advice. For specific advice applicable to your business, please contact a professional.

Similar Threads
Tips to make your business feel more inclusive to LGBTQ+ customers
Spread the Word: How to choose the right advertising platform for your business
A Balancing Act: Community Members Share Insights about Running a Business and Family Life
Future of Commerce: 4 Key Takeaways from 2024 and Insights from the Community