What do you call the season before your busy season? If you guessed “the obstacle course”, come see me about claiming your prize.

But in all seriousness, obstacle courses present new challenges at every turn. You’re forced to assess them, address them, and move quickly to the finish line before time is up.

Such is holiday season preparation for retailers, with the finish line presenting itself as Black Friday.

All the work that small business retailers put in before Black Friday sounds stressful (and it is). But these obstacle courses are also games at their core and games are meant to be fun. So, let’s take a look at some of the top challenges retailers come upon when preparing for the holiday rush, and let’s have a little fun figuring out how to tackle them.

SMB Challenge #1: E-commerce vs. In-store

Small Business Challenge 1 - E-commerce vs. In-store

More than ever, customers are expecting retailers to give them the convenience of shopping and browsing online – from wherever they are, whenever they want.

The convenience of visiting a store virtually and finding the same product(s) at the same price, and then receiving it at home without the crowds and lines…it’s something you can’t really put a price on (pun intended?).

But one thing is for certain, e-commerce is absolutely necessary for retailers. In fact, it can make or break a consumer’s choice to spend their hard earned money with you or the guy down the street.

For some, the challenge is taking that final plunge into online retail. For others, it’s deciding what to sell online versus what to sell in-store. And then, there’s managing inventory across all points of sale. And finally, what you do about online vs. in-store returns at the end of the holiday season.

Regardless of those questions, if you’re not online in some way, shape or form, your business is likely declining. Bite the bullet and open up an Etsy account or stand up a basic website. We have the perfect guide to help you decide where to start. (And it even dives into inventory management and returns too!)

SMB Challenge #2: Marketing and Brand Differentiation

black boot on display at retail store

It should be easy to explain why your shop is great. But it can be more challenging to explain how your shop is different.

When mapping out your holiday marketing plan, challenge yourself to focus on what the customer wants to hear, not on what you want to tell them.

Do they care more about the unique qualities of the products you sell? Or perhaps the story behind why you sell your products is more compelling to them. Tap into some thought starters and see what has worked for other retailers before diving into the same ole marketing routine this year.

SMB Challenge #3: Selling Products By People, To People

Small Business Challenge 3 - Selling

Face it, if you’re in the retail business, you’re in the people business. It’s your job to balance the people and personalities that sell your products with the people and personalities that want to buy your products.

Staffing up around the holidays and finding extra help can be hard, but it’s mission critical to connecting with your customers. Similarly, investing in customer engagement and loyalty programs can make the difference between a so-so holiday and woo-hoo holiday. Read up on ways to invest in the people that make your business successful and try a few new ideas this season.

Every obstacle course is different, but many of the challenges stay the same. These are just a few of the top to tackle, but there are plenty more out there. Just remember, you’re not the only one working toward the finish line and you can borrow best practices from others anytime.