Your 2020 small business holiday to-do list

On a scale of one to ten, how organized are you for the upcoming holiday rush?

Whether you’re a confident nine or an apprehensive five, the festive season is typically a busy time, both professionally and personally, for everyone. And this year, marketing during the holiday season might feel like navigating uncharted territory.

Even in challenging times, people will still want to celebrate and exchange gifts. You should plan your holiday marketing strategies accordingly to get the most from this period of increased customer spending.

We've created a month-by-month to-do list of holiday marketing tips, starting in October, to help you tackle the upcoming holiday rush and make meaningful connections with customers.

October holiday marketing tips

Pumpkin patches and cooler weather might be top of mind in October, but don't miss your chance to get a headstart on holiday marketing.

  • Devise a detailed holiday plan. Doing a little prep and planning ahead of time allows you to skip much of the frenzy and feel more festive when the holiday season suddenly arrives.
  • Create a holiday budget. Keep it realistic and stick to it.
  • Get inspired. Check out what other businesses do during the holidays by perusing Pinterest, looking at their Facebook advertisements and Instagram posts, or engaging in a discussion board to gather learnings.
  • Do some market research. What are your customers looking for this holiday season? How will you meet those demands?
  • Prepare your inventory. The holiday rush will be upon you sooner than you think. Get your high-season inventory ordered, and in order.
  • Order your advertising materials. Now is the time to get marketing materials for these sales. Whether banners, postcards, flyers, posters, or foam boards, start stockpiling supplies to carry you through the rest of the season.
  • Get what you need for holiday packaging. Decide how you want to package mail orders and wrap in-store purchases - consider including a sticker single with every order, using customized shipping tape, and wrapping delicate items in tissue paper.
  • Plan your Black Friday or Cyber Monday sales. What sales are you running? When does each sale launch? How will you advertise the sales? Start drafting promotional emails now, so you'll be ready to hit 'send' when the time comes.


These are two of the year's biggest sales days - but you don't have to wait until the end of November to run a promotion. Offer daily deals & subscriber-only sales to entice new customers.

November holiday marketing tips

November is home to two key shopping holidays: Black Friday and Cyber Monday. Since these two sale holidays are later in the month, think about launching an early November promotion to attract proactive shoppers. And as you prepare for these major sales, don't forget to decorate your storefront (digital and real-life!) and announce your upcoming promotions.

  • Decorate your storefront. If you have a brick and mortar, deck out your storefront with festive window art, banners, and decals. Inside, play your favorite holiday music and light some wintery candles (look for scents like cinnamon and evergreen) to set the mood. Also consider hosting virtual or limited-capacity events and personal shopping appointments.
  • Deck out your website. If you have a website, update it with holiday-ready (on-brand!) details - maybe a mistletoe-inspired homepage banner or curated gift shop page.


New offerings this year? Whether you're curating an online gift shop or selling festive face masks, let customers know ahead of time with an e-newsletter, postcard, or social post.

  • Order thank you cards or gifts like mugs, calendars or branded promotional items with your logo on them. The holiday period is a great time to thank your customers and employees, and to strengthen your relationships for the upcoming year.
  • Order your holiday cards in advance. Make sure you order enough for your customers and employees. It’s easy to underestimate your needs in this area, so order more than you think you need.


Extra holiday cards? Tuck them into mail orders or shopping bags for a festive finish.

  • Launch your Black Friday sale. The day after Thanksgiving is a pivotal day to market to your customers - use clear discount messaging to drive interest and understanding. To avoid overcrowding this year, consider using a time-slot or appointment-based system for in-store shopping.
  • Participate in Small Business Saturday. This year, Small Business Saturday is November 28th - create a special offer or run a promotion during this weekend.
  • Launch your Cyber Monday sale. The Monday after Thanksgiving weekend is another major sales day. Take advantage of this cyber holiday and promote exclusive deals (like early shopping access!) for email subscribers and social followers.
  • Hang posters and banners. Announce upcoming sales to attract potential customers and interest existing customers.

December holiday marketing tips

As the holiday shopping season winds down, use this month to say 'thank you,' reflect on your successes, and look ahead.

  • Record and analyze the results from your Black Friday and Cyber Monday sales. Make notes of what worked and what didn’t to give you insights for the next holiday season.
  • Review shopper frequency. Were you quiet in the morning with long (socially-distanced!) lines in the afternoon? Understanding typical in-store foot traffic will help you organize effective staff schedules for next year.


Thank your customers and employees with handwritten cards or promotional items with your logo.

  • Consider a refresh. Think about re-examining your branding for the new year. This is an excellent time for some fresh thinking around your visual identity, whether it's an update to your logo or overhaul of your website.
  • Reflect on what to improve for next year. Order too much of something that didn’t fly off the shelves as expected? Run out of staples like branded bags halfway through the holiday rush? Learn from it, move on, and add it to your checklist for next year.
  • Prepare to hit the ground running in January. Whether it’s stocking up on inventory or creating a calendar with key dates (like staff holidays and seasonal promotions) having a plan will help you kick off 2021 on the right foot. After a successful holiday season, you should get back to work feeling rested, rejuvenated, and ready to take on another year.

So, whether you’re thanking customers and clients, encouraging more visits to your store, or trying new marketing tactics, this year's outcome can help inform what you do next year...though the world could be very different in 2021.

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