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Preparing Your Small Business for the 2020 Holiday Season

Written by: Corey Harris & Julie Traxler, Executive Contributor

Executive Contributors at Brainz Magazine are handpicked and invited to contribute because of their knowledge and valuable insight within their area of expertise.


A few weeks back, during an early fall camping trip, six of us sat around a campfire enjoying classic rock and adult beverages. There was plenty of laughing while telling stories, but the conversation inevitably wound its way to how unfathomably frustrating 2020 has been personally but especially frustrating for small business owners. As small business experts, we spend most days supporting entrepreneurs and small business owners, so it’s easy for us to see the ravaging effects that COVID-19, government decisions, murder hornets, and conjoined hurricanes have had on small businesses. But many Americans don’t realize the level of devastation small business owners continue to experience as the realities of 2020 linger.

As the night drew closer to morning, the passion of the discussion became almost as heated as the freshly stoked fire. All six of us sitting around that fire have good reason to be feeling frustrated, angry and overwhelmed. We’re all small business owners, and like all of our entrepreneur counterparts, we are exhausted from all of the uncertainty.

That’s why we decided to take as much control back as possible and craft a 2020 Holiday Strategy to bring some certainty into this chaotic and crazy world. In a year where we haven’t seen a “normal” holiday since New Years Day, we’re keeping our expectations low for large-scale gatherings, but we’re raising our expectations for how families and close friends celebrate together. Sure, belts are likely going to be a little tighter for everyone this year, but that doesn’t mean people are skipping Christmas. Though, it probably means people are going to be more discerning about where their money is going.

So how do small business owners answer to consumers spending less money and being more discriminating where they spend it? With a sound strategy that prepares them for holiday shopping in a COVID-19 world and the ability to pivot quickly, if needed. Here are some strategies that small business owners can enlist to help make the 2020 holiday season the least stressful part of the year.

1. Spend time imagining

This might sound a little foo-foo for some of you, but hear us out. We need to spend more time working on our imaginations. Imagination is important in business because it helps to bring a vision to customers on how things can be, and that drives engagement. The alternative to using our imagination is to use our memory, which means we’re working off history.

While history tells us what we’ve already done, it doesn’t tell us how to pivot or get creative or try something new. And even if you’ve used the same sales and marketing plan for the past 10 holiday seasons, we can all agree that this holiday season isn’t going to be like last year. While this may seem obvious when you read this, it isn’t to many small business owners. Don’t do what you’ve always done.

Now let’s consider the first 9 months of 2020. Yes, it will be helpful to remember how you were able to survive the spring and summer, but it’s time for a new approach. It’s time to spend some time using your imagination. We don’t know many small business owners who spend time with their team (or themselves) imagining, but it’s time to start. Schedule a session with your team, turn off the phones and laptops, remove all the “rules” and imagine what this holiday season could look like for your business.

2. Know how your customers feel about the pandemic

Here’s the deal. Everyone should be aware that businesses have “COVID Compliant” practices in place now. Your mission is to understand if your customers want to continue to hear about your sanitization practices or if they would rather you never mention it again. We aren’t suggesting you push fluff, but you can get your messages across without mentioning current events.

The reality is we have all been inundated for months now about how a business is responding to the pandemic, how the store you’re visiting implemented new cleaning practices, and what company X is doing to give back.

As a small business owner, you have to find an approach that informs your customers but doesn’t alienate them. And that looks different for every business. We recently interviewed a neuromarketing specialist on our podcast, BizQuik, and we asked him for his thoughts on how small business owners should talk about COVID-19. “Treat COVID the same way you treat salt when cooking. Sprinkle it in to enhance the flavor. It’s not the main focal point of the dish.”

Hint at what’s going on by solving a problem your target market may be experiencing. Anyone who reads or views your messaging will understand why you’re doing what you’re doing without having to be told so

3. Prepare. Prepare. Prepare.

Every business, small or large, had to pivot in some way this year to respond to the pandemic. But for the most part, that's all it was. A response. A reaction.

Restaurateur and entrepreneur Nick Kokonas said it best when he was a guest on The Tim Ferriss Show podcast:

"If you're acting as a reaction to a really bad situation, it's very easy to make bad decisions quickly"

And there were many bad decisions made this year. You're probably cringing now thinking of some misstep you made. We sure are. But if you plan and strategize now, you will finally have the upper hand on this pandemic. Use that to your advantage. Yes, it's true there are many unknowns, and it's impossible to predict every government regulation that may get passed down or disaster that may strike, but that doesn't mean you can't be prepared for the holiday season. Start by anticipating potential changes to your business, customer base, supply chain, or anything else that will stop you from being successful.

Where are there holes? How can you fill those holes or make a pivot so that you aren't impacted? Can you prepare a pivot plan now just in case you need to use it later?

It's also a good time to either review and update or start documenting your pivots, what worked, what didn't, and everything you did. Keep track of your changes, communications, reactions, etc. This information is likely to come in handy in the future. Don't forget to include the plan to "unpivot" if necessary.

And it's also a really good time to get a fresh pair of eyes on your preparations. If you haven't been regularly engaging someone from outside your business over the past 6 months, now is the time.

4. Stand out

Let's get back to imagination, because customer acquisition requires imagination.

Find a way to tell a compelling story and offer up something that your competitors aren't. This goes beyond offering discounts or margaritas to go (though that's a delicious option). Those are business qualifiers now.

Traditionally Black Friday and Cyber Monday are huge days for sales, but most small business owners need more than one or two big days during the holiday season, especially after the year we've had. And because we have all gotten used to doing as much digitally as possible, the demand for running ads on social media is expected to spike, meaning we're likely to see the cost of those online ads skyrocket this holiday season. Is there a better way for you to spend your marketing budget?

Get creative with your content. Double down on creating content that connects with your customers. Get outside of your comfort zone. Use content that hits on more than just vision. Creating videos is an easy way to be more personal with your target market. Host a Q&A session to allow for customers and clients to interact with you. Use that imagination.

That doesn't mean you shouldn't continue to use more traditional methods such as using loss leaders to drive more sales or taking advantage of holidays outside of December.

Halloween or Veteran's Day sales are a great way to drive sales or simply as a tool to stay relevant. You can try to create a sense of exclusivity by offering private shopping events, appointment booking for shopping your brick and mortar, or creating limited-time offers. We're all still human and will connect with something that conjures up memories of better times.

It's also a good time to either review and update or start documenting your pivots, what worked, what didn't, and everything you did. Keep track of your changes, communications, reactions, etc. This information is likely to come in handy in the future. Don't forget to include the plan to "unpivot" if necessary.

And it's also a really good time to get a fresh pair of eyes on your preparations. If you haven't been regularly engaging someone from outside your business over the past 6 months, now is the time.

5. Planning for 2021

You've weathered the storm that is 2020, and now it's time to map out your plan for 2021. If we're being honest, we're probably all going to be relieved when 2020 is over and maybe a little cautious because we may not see the end of this anytime soon. When the clock strikes midnight on January 1st, we'll begin the year with hope, but hope isn't a strategy, so we also need a plan.

Here's the good news, you're at least partially prepared, based on all the lessons you've learned in 2020. And as much as we want to believe you won't repeat any of the difficulties of this year, we want to point out how quickly humans forget. As soon as the economies open back up, people regain confidence in going out, there's more money to spend, and people are yearning to return to "normal" (not the "new normal" but the normal we had in January of 2020), our collective memory begins to fade. We should have all learned that with the collapsing economy of 2008. Many people suffered huge financial losses during that crisis. Those losses should have taught all of us to save more and spend less.

To be prepared. And if we've learned anything this year, we've learned you can't predict what's going to happen next. So, even though things will likely return to normal relatively soon, we all know at some point something else is going to happen. Be prepared. Have a plan.

As a small business owner, you know how quickly things can change and how quickly your attention gets shifted. While the events of the last 6 months are still fresh, document everything you did.

You don't need to be extremely detailed, but you need to document at least enough to help jog your memory if something similar happens again.

All in all, small business owners should feel optimistic heading into this holiday season. With the right amount of preparation, creativity, knowledge, and imagination, the 2020 holiday season can be a successful one for small business owners.

If you’re thinking of opening your own small business or want help improving one you already operate, you can connect with us on LinkedIn, Instagram, Facebook, or Twitter or visit our website.


Julie Traxler and Corey Harris, Executive Contributors Brainz Magazine

Julie and Corey started their company, SB PACE, as a result of the 2020 pandemic in order to provide assistance to small businesses. Since then, they have expanded into helping start-ups, companies who are looking to improve, and small business mergers and acquisitions. They wrote the book on small business disaster preparedness and continued to help small businesses by leveraging their knowledge and experience working for Fortune 500 companies and Big Four consulting firms. Julie and Corey are the experts small business owners turn to when looking for sustainable, long-term success.



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