The Holiday Season Planning Guide for Small Businesses

By Lucy Reed (

The holiday season can be the most lucrative time of the year for business owners who play their cards right. Customers and clients tend to be in a good mood and are more willing to splurge: Americans spent over $1041 on gifts and non-gifts in 2019, according to Tally, and the numbers just keep climbing.

If you’d like to have an especially-profitable holiday season, whether you’re a retailer or service provider, start planning now –the earlier you start, the less likely you’ll drop the ball on important details. You will need to come up with an effective schedule, brainstorm some creative marketing strategies, and get your cash flow in order. 

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Strive to generate customer loyalty

Your customers and clients are your lifeblood, and the holiday season is the best time to acknowledge that fact. Consider sending out holiday cards and emails, perhaps with a discount, to the people who frequent your business, and set up a loyalty program if you are able. It creates goodwill and makes it more likely they do business with you again – this year as well as the next.

Give back to the community

Consider giving back to the community while you’re thanking your customers. Some ways to do so are supporting a cause you believe in, organizing a fundraiser, or sponsoring an intern or two. Giving back not only helps your community out but also creates positive press for your company. Don’t forget to include your employees too, whether that’s by giving them extra time off or offering an end-of-the-year bonus. 

Think up an appropriate promotional strategy

A full-fledged, customized marketing strategy is a must. You will need it to incite buyer interest, stand out from the crowd, and just get into the holiday spirit. Some avenues to explore include paid advertising, social media marketing, holiday ad copy, email marketing campaigns, and offline holiday events. Make sure you lead with discounts and promotions – customers and clients will expect it. 

Double-check your inventory

If you deal in physical goods, take stock of your inventory levels. Make sure you have enough goods on hand to account for the heightened demand. Furthermore, it may be a good idea to stockpile goods specific to the holidays. For example, retailers could order foods, candies, beauty products, and clothes that are tailored for Christmas or New Year. Market conditions and past buyer behavior can help you determine what’ll sell. 

Make sure to account for your customers’ and clients’ needs

Your customers and clients may have preferences and needs for the holiday season. You can boost loyalty and rack up more sales by catering to them. For example, retail customers often prefer extra payment options or have specific delivery or gift-packaging requirements. For service customers, you may have to keep your clients’ holiday schedules in mind and meet increased demand around certain times.   

Optimize and stress test

You will probably witness an increase in visitors – online to your website and offline to your office or store – around certain significant dates (such as Black Friday or Christmas). Make sure both your website and shop or office can cope with the rush. A slow-loading website or a tardy checkout process could raise customer ire and cause you to lose out on potential sales. For best results, make sure everything is snappy. Hire extra workers if you have to.  

Staff and train workers

Many businesses take on seasonal workers to meet the heightened demand (and sometimes keep them on long-term). Recruit early to ensure you get workers and have enough time to train them. Keep in mind that your employees represent your business, so extra efforts may be warranted to find good workers. You can advertise online and offline, network, and ask for referrals. If you’re too busy to recruit personally, you could hire a staffing agency. Their recruiters can screen profiles on your behalf and help you connect with top-tier candidates conveniently.

Set up a holiday schedule

Spruce up and redesign 

Holiday schedules are your best friend. They give you a timeline for your marketing strategy and also help you make organizational decisions – like accounting for employee leaves and client demands. Once you have a holiday schedule prepared, be sure to communicate it to your workers, stakeholders, associates, and customers. Update your website and business listings while you’re at it.  

Decorations are a great way to usher in the holiday season, attract customers, and make your employees happy. If you have an office or store, put up some lights, arrange some props, hang up pictures and banners and decorate in other ways. If you have a website, add some seasonal graphics, images, and interactive content. Around Thanksgiving is usually a good time to begin decorating and make changes. 

Take a look at your financials

The holiday season may be profitable, but it’s also accompanied by many expenses – decorations, overheads, overtime pay, bonuses, holiday inventory, and much more. You will need liquidity – cash on hand – to manage. Make sure you have enough and consider setting up a line of credit if you need to.  You can also consider ways to boost cash flow – like offering pre-sales and selling gift cards. 

Give yourself a break

With the increased activity and added organizational demands, comes heightened stress. Most small business owners have extra work on top of their usual duties, not to mention personal demands on their time. It can be extra tough for retailers and hospitality businesses, as the holidays are usually make or break for them. Do your best to look after your mental and physical health during this time. Spend time with friends and family, exercise, and get plenty of rest.


As you can see, holiday season planning can be quite a challenge. Getting organized and planning ahead are keys to success. Also, don’t forget to collect holiday data over the next few weeks. The holiday season is a recurring event, and you can improve your offerings and generate better results by learning from previous years.  

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