How to Make This Holiday Season Your Most Seamless and Successful Yet

How to Make This Holiday Season Your Most Seamless and Successful Yet
If the thought of the impending holiday season makes you break out in a cold sweat instead of warm fuzzies, it’s time to get serious about preparation.
by Square Oct 16, 2018 — 3 min read
How to Make This Holiday Season Your Most Seamless and Successful Yet

This article was updated on 10/27/2022.


If the thought of the impending holiday season makes you break out in a cold sweat instead of warm fuzzies, it’s time to get serious about preparation. Here’s what to do to get set for a jolly holiday — not a season of stress.

Forecast your busiest times

Data is your best tool in preparing for the holidays. Luckily, you have loads of it at your fingertips in your Square Dashboard. There, you can look back at your historical sales data to help you identify which November and December days were your busiest last year. You can even drill down further to figure out your peak sales hours. These data points can help you be strategic about setting your holiday hours and planning employee schedules.

Plan your inventory

Items go fast during the holiday season, and it’s important to make sure you’re prepared for when they do. Square for Retail on Square Terminal lets you know which stock will run out based on how fast you’re selling and recommend items to reorder. You can also opt-in to automatic purchase orders and Square will automatically generate purchase orders for your items that are running low. 

To manage your inventory needs on the go, Portable POS solutions like Square for Retail can scan and search items with the counting tool to update, review, and confirm counts right from your iPhone or iPad.

If you’re interested in streamlining your inventory management in other ways, you can hook your Square account up to a variety of inventory tools in the Square App Marketplace.


Plan seasonal email marketing campaigns

Email marketing is a great way to engage your customers—and rake in more sales. To cut through the late November and December noise, try getting jump on things with pre-Thanksgiving sales and offers. Also think about sending targeted messages, like special deals for your loyal customers, or a two-for-one offer for people you haven’t seen in a while.

This is easy to do with Square’s email marketing software, which automatically segments your customer lists into loyal, casual, and lapsed. The software comes packed with ready-to-go templates for promotions, events, and announcements, so you can quickly send out beautifully-designed emails. It will also have special email templates for Thanksgiving, the holidays, and New Years.

Meet your customers where they are

A line out the door is always a good thing. But to avoid impatient customers, be prepared with a way to speed up the checkout process. Portable POS Solutions allow for you to make a sale wherever your customers are in your store, personalizing the customer experience and increasing your ability to lock in those sales. With Square for Retail on Square Terminal, you can even take your purchase to the next level by offering your customers flexible payment options like Afterpay or Cash App so they can pay their way.

Enable offline payments

Blame it on Murphy’s Law, but sometimes, things tend to go wrong at the most inopportune times—say, your internet goes out during a sales rush. To make this less of a catastrophe should it happen, enable offline payments on your Square account. That way, you can still take payments, even if you’re not online.

Clean up the items in your POS

Now’s the time to make sure that everything’s as simple as possible in your items library. You want to make it quick and easy for your staff to ring people up during your busy times. Sit down and go through all of your items, deleting ones that you no longer offer. It’s also a great opportunity to add in photos for all of the items you have on tap.

Get your staff ready

Gather your employees who were with you last season and have a serious, no-holds-barred conversation about how the holidays really went last year. What went well? And, more importantly, where did you fall short? Being polite won’t help your business, so get their honest feedback, and ask them if they have any suggestions about how you can all do better this year.

For example, should you hire seasonal employees? If so, do you have a solid training protocol in place? Your staff determines your success and failure, so make sure you have a team you can count on. To make sure you have the best people on board, read our post on How to Find Great Seasonal Employees.

Finalize time-off requests

There’s no point in training a competent staff if all your employees are taking days off during your busiest times. So, require employees to put in their time-off requests early, and set certain parameters that make sense for your business, like “if you don’t work on Black Friday, then you have to work on Christmas Eve.” You don’t want to be scrambling with last-minute schedule changes, so make the calendar a priority.

Update your website and social media

If you have special holiday hours, make sure that your site has the most up-to-date information. And if you’re opening early or closing late, post the news on Twitter, Facebook, Instagram, or another social media outlet of choice — especially if you’re running special promotions during these times.

The Bottom Line is brought to you by a global team of collaborators who believe that anyone should be able to participate and thrive in the economy.


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