8 steps to prepare your small business (or freelance gig) for the holidays

In this 6-minute read:

  • Determine holiday hours well in advance
  • Adjust online listings
  • Resolve staffing issues and time off
  • Order inventory and supplies (if you can)
  • Decorate your store and website
  • Streamline your POS and checkout processes
  • Take advantage of holiday marketing techniques
  • Collect customer info for loyalty marketing

The holidays are crazy busy for local businesses (along with everyone else!). But small businesses have it super-rough because they often don’t have the extra staffing or resources needed to take full advantage of the retail frenzy. During these weird times of the pandemic, it becomes even more difficult since supply chain issues and hiring problems are at an all-time high.

Still, it’s a good idea to do what you can to get your small business as ready as it can be for the holidays (including your freelance/gig-worker/self-employed business). Got caught up and are behind? There’s no time like the present to get started. Any effort you put in can pay off big during this huge sales period.

Here are 8 steps to get your small business ready for the end-of-year shopping season and come out ahead throughout the new year. (Plus some tips for freelancers, gig workers, rideshare drivers, etc.)

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1. Determine your holiday hours, update your signage and online listings accordingly

The first thing you need to do is figure out your holiday schedule and hours of operation well in advance. We’re talking September/October if possible. (Obviously if you’re reading this in December, you’ll need a time machine, or plan ahead next year.)

If you’re planning on extending your hours, make sure you put up the new signage and post them on your website,  YelpGoogleFacebookOpenTable, and TripAdvisor, and all your other online listings.

If, on the other hand, you’re planning to cut some hours or close your doors for certain holidays to allow yourself or your employees to spend time with family, be sure to let customers know well in advance so you don’t disappoint them.

Freelancers, gig workers, and the self-employed should also plan ahead here

This is equally important for freelancers, gig workers, and self-employed individuals who have typically worked to a schedule or cadence that your clients have come to expect. If you’re planning on slowing down and taking some time during the holidays to recharge and plan, be sure to let them know so they will have a good impression of you rather than be disappointed if they need something done and you’re not available without notice.

small business holiday hours

2. Plan ahead for staff time off, hire temp holiday workers if needed

Another thing ideally done by October is resolving any staffing issues or time-off conflicts. Everyone wants to take time off during the holidays, but it’s also crunch time for local businesses who need every hand on deck. Again, during the COVID years this has come to be even more difficult than ever.

If you’re a local business owner, you likely don’t have a large pool of backup employees to take the place of your regulars. You might consider offering key employees bonuses or time-and-a-half for working key holiday shifts.

If you are unable to fill slots using your regular staff, consider hiring temporary workers. Customers will be a lot happier (and leave you better reviews) if they are able to complete their purchases efficiently and quickly. 

small business holidays christmas

The extra expense of hiring extra help is frequently justified by the increase in purchases and revenue during the holidays.

3. Order any extra supplies and inventory you might need (if you can)

Many small businesses do the majority of their yearly sales between September and January. Make sure you have the inventory on hand to cash in. After all, you can’t sell it if you don’t have it! 

If you have a good small business software platform, you can examine last year’s holiday revenue trends and plan more accurately for what you’ll need for this year. This also helps prevent over-buying and ending up with stock rooms full of merchandise that takes months for you to sell.

Does your shop offer gift wrapping? Be sure to order wrapping paper, ribbons, bows, tape, gift bags, etc. If you haven’t offered gift wrapping before, consider it. It can be a huge draw for customers.

NOTE: post-COVID, the supply chain can be very iffy and you may not always be able to get the supplies and inventory you need, particularly if you wait until the last minute. Some things can take weeks or even months to come back in stock at wholesalers. This is a problem for many businesses, large and small, so do what you can, apologize for things that are out of your control, and look for ways to fill in the holes in your inventory or services with substitutions until the supply chain issues are resolved.

4. Decorate your store (and website) for the holidays

You know how it looks when every house on a street has holiday lights but one? Your store looks the same way when you don’t decorate. So be sure to order up a good supply of holiday decorations along with your inventory.

Whether you’re firmly in the Christmas/Hanukkah/Kwanzaa camp or prefer the more generic “holidays” theme, there are tons of options for you.

small business holidays

While it’s great to get into the spirit of the holidays, it’s important not to lose sight of the fact that the reason you are enticing people into your store is to purchase, not to admire your holiday decor.

We’ve been to stores whose aisles and shelves were so overwhelmingly jammed with holiday bling that we’ve had a hard time telling what’s for sale and what’s for show, let alone navigating a crowded shop without knocking anything fragile over.

Another thing to be aware of is heavy perfumes, scented candles, and those horrible fake-cinnamon-scented pinecones can choke many potential (even allergic!) customers and drive them away from your doors, so be considerate.

tangled holiday lights small business

Despite these potential pitfalls, most people have favorable responses to the (natural) scents of fresh-baked cookies, pine needles, and/or warm spices like allspice, clove, cinnamon, and nutmeg.

Don’t forget to add holiday graphics and appropriate messaging to your website and social channels! (And set reminders so you don’t forget to update them quickly after the new year.)

5. Take part in Small Business Saturday 

Small Business Saturday is a yearly event that takes place the Saturday after Thanksgiving, and is a great opportunity for you to network with other local businesses and take advantage of the “shop small” movement.

American Express offers a useful resource to help you make customized artwork to show your support for Small Business Saturday and entice local shoppers to your door. Click here for your free templates and ideas you can share in your store and online!

If you missed out this year, be sure to plan ahead for next year. And don’t worry, because even if you didn’t max out your profits during the Black Friday/Small Business Saturday weekend this year, the 2 weeks before Christmas are even more profitable and can account for a third of holiday sales.

6. Streamline your point-of-sale and checkout processes

This hectic time is a great opportunity for you to reassess your Point Of Sale (POS) platforms and processes, and make sure you stand out by making the holiday shopping experience smoother and faster… not the other way around.

You might consider upgrading to a faster, more modern small business POS system, and/or offer customers more options for how they wish to pay. 

For example, if you have the space and the staff available, consider dedicating one register to cash-only transactions, and others to card or digital transactions so people know what to expect.

small business POS holiday card

This can streamline the checkout process and leave customers with a positive impression, which can result in greater customer loyalty, better online reviews, and improved local SEO.

7. Create holiday sales and marketing campaigns

Everyone loves a bargain, and nothing brings customers to your door like a good old-fashioned holiday sale.

Due to the increases in foot traffic, local businesses can often generate greater revenue from smaller transactions, since there are many more transactions than average.

Of course, cost/benefit ratio is key here, but if you can market a 10% or 20% off sale with physical signage in your store, banners outside, and digital blasts out to all your email lists and social media followers, you can really generate some business.

Consider offering a free gift with any purchase, or free gift wrapping, or any other perk or benefit you can think of that makes sense for your clientele. Freelancers, gig workers, and self-employed individuals will need to modify this strategy as appropriate to their customer base and industry, but going the extra mile to make people feel special during the holidays can make you more memorable and earn repeat jobs in the future.

small business holiday gift wrapping

Of course, all this increase in traffic will only be temporary unless you really take advantage of the true value of repeat business by gathering customer contact info, which brings us to our next point (See #8 below).

App-based drivers can get into the holiday spirit just like local business owners

Uber and Lyft (rideshare company) drivers can make each rider’s night out with the girls or holiday shopping trip even more memorable by offering special perks, like Christmas-themed treats or small gifts to their riders, and playing holiday music in their cars. You may even consider spice-scented air fresheners or holiday lights in your car to make it extra cozy.

These small can add up to better driver reviews for you, as well as an increase in tips. Plus the increase in local foot traffic, bar patrons, and restaurant diners means more people looking for Uber and Lyft rides. Also, the shortage of drivers during the pandemic means that prices have increased and that means more bank for you if you choose to drive during one of the most lucrative periods of the year for app-based drivers.

A note for freelancers, gig workers, and other self-employed individuals during the holidays

For freelancers, gig-workers, and the self-employed, the holidays can be huge business or it may be somewhat slow, depending on your industry. Lots of larger companies have a slowdown in the week or so closing in on Christmas, and many shut down almost completely during the week between Christmas and New Year’s Day. So getting a freelance writing job might not be easy during that time.

On the other hand, some companies take this “slower” period to reset and plan for the coming year, and getting ahead on content writing, front end developing, graphic design, marketing forecasts, video content creation, etc. may be just what they’re looking for. If you feel like you want to get a lot done during the holiday season, there’s plenty of opportunity for you to do so if you find the right jobs.

Regardless of your plan, be sure to communicate your intentions to your clients so they know what to expect.

8. Capture customer/client info to build loyalty and return business

Repeat customers spend 300% more, according to this data. But you can’t get all these new customers back in your door to spend with you if you don’t know who they are.

It’s vitally important to do everything possible to get customers’ contact info. 

Don’t feel weird about asking. Studies show 86% of customers say they actually want promotional emails from businesses they like.

small business POS holidays checkout

Add an email field to your checkout processes, or if you want to go old-school, ask people to write them down on a clipboard or insert a business card into a bowl for a weekly prize.

Ideally, though, you should be using a small-business customer management solution that adds customer contact info, transaction history, and other key data, and keeps it updated with every transaction. If you want to learn more about Womply’s “pre-populated” customer directory, sign up for Womply Free and see how it works. Plus, get free reputation monitoring and customer insights!

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