The annual holiday shopping season typically gives retailers an opportunity to increase sales. Or for some businesses, earn the majority of their annual revenue. But the end-of-year shopping months also come with more risks for any business, including crowded stores, increased deliveries, technology bottlenecks and small teams stretched thin. Is your retail business or online store ready to safely navigate the rush?
Proper planning can help your business make the most of the season and reduce the risk of mishaps. And reviewing your retail business insurance now can help you assess whether your current coverage still fits your holiday operations.
What else can small business owners do to maximize the season with the least amount of risk? Follow these nine tips, many gathered from owners in the trenches of holiday planning, to help you navigate the busiest time of year with less stress.
1. Plan more, stress less
Whether you sell in a physical store, online or both, holiday planning starts well before the decorations go up. Thinking through inventory orders, promotions and daily operations now can help you manage the rush with fewer last-minute surprises.
Get organized with these steps:
Review last year’s sales: According to the National Retail Federation, 2025 holiday sales grew 4.1% last year. Look at old receipts, POS reports and order histories to see which products moved fastest for your business during last year’s holiday season. Use these patterns to help guide this year’s orders and promotions.
Build your holiday calendar: Mark down key dates like Black Friday, Small Business Saturday, Cyber Monday, shipping cutoffs and local events. From there, work backward to schedule inventory orders, staff training and promotional messages.
Joel Goldstein, president of Mr. Checkout Distributors, recommends thinking beyond the pre-holiday rush. “Plan the week after Christmas as carefully as the week before, since gift cards and returns bring people back in with money to spend” he says.
Organize your space: Set up stockrooms, packing areas and wrapping stations so supplies are easy to find and walkways stay clear. Assemble boxes and gather packaging materials before orders pick up.
Evaluate your return policy: Consider whether your return window gives early shoppers enough time to exchange gifts after the holidays. Clearly communicate any seasonal changes on your website, receipts and checkout signage.
2. Don’t overbuy holiday inventory
The holiday season doesn’t necessarily mean you need more inventory. It means you need the right products. Excess inventory can tie up cash, while underestimating demand can leave you scrambling.
Retailer Andy LaPointe, co-founder of Traverse Bay Farms, starts by identifying the products he doesn’t want to promote. Narrowing that focus helps his team allocate inventory space and fulfillment resources to the products they want to prioritize.
“Sometimes the smartest way to handle holiday demand is deciding which demand you don’t want to create,” LaPointe says.
Use these strategies to keep your inventory manageable:
Choose what to prioritize: Review sales trends, profit margins and available storage before deciding which products to feature. Avoid promoting more items than your team can realistically stock, pack and ship.
Plan for small orders and reorders: Ask suppliers about lead times, minimum orders and restock availability. Goldstein recommends ordering early in smaller, more frequent quantities, then reordering based on what’s actually selling.
Be careful with seasonal packaging: Holiday designs can look appealing, but leftover stock may be difficult to sell after December. Goldstein warns against overbuying packaging with a short seasonal shelf life. Instead, look for options you can use year-round.
Track inventory in real-time: Use your POS system or low-stock alerts to monitor popular products. If you sell online and in-store, keep inventory counts aligned so you don’t accept orders you can’t fulfill.
Set clear expectations: Post accurate product availability and shipping deadlines online. Train staff to explain restock timing and suggest alternatives when an item sells out.
3. Strategize holiday promotions that work
Large retailers may have massive holiday campaigns, but small businesses can stand out with thoughtful, well-timed personalized promotions.
“On promotions, the independents that win don’t try to out-discount the chains,” says Goldstein. “They lean on what a chain can’t do, like a separate display of local products, a staff member who can actually recommend a gift and a checkout that moves fast when the line is long.”
Build your promotions around the things that make your store worth visiting:
Focus on gift sets and bundles: Group complimentary products into ready-to-give packages. Bundles can make shopping easier without requiring a deep discount.
Keep it simple: Pick one or two manageable promos, like an early-bird discount in November and a featured gift collection in December.
Highlight local finds: Create a display or online gift guide featuring local makers and regional products. Give staff a few details about each item or maker so they can help shoppers choose.
Cross-promote: Partner with a nearby retailer on a joint offer or exchange gift recommendations. Choose a business with complementary products and agree on the details before promoting the offer.
Create urgency: Remind shoppers when a promotion ends or when they need to order for holiday delivery. Keep messages consistent with your shipping estimates and available stock.
Include a small gift with purchase: A sample or complimentary item can introduce customers to another product you carry. Factor its cost into the promotion and clearly explain purchase requirements.
4. Use digital platforms and social media channels for sales
Social media can help you show shoppers what’s available and make it easier for them to buy. Plan your content around the products you’re prioritizing and the questions customers ask most often.
Keep your info current: Update your business listings, social profiles and your website with holiday hours, contact details and pickup instructions. And adjust your scheduled posts if featured products sell out.
Show behind-the-scenes moments: Share short videos of holiday prep, staff wrapping orders or new arrivals since these glimpses make your business feel approachable.
Create quick gift guides: Curated gift guides or personalized product recommendations help busy shoppers quickly find the right present. Use Instagram Reels, TikTok videos or a blog post to highlight product suggestions like “Top 5 Gifts Under $25” or “Gifts for Teachers.”
Make posts easy to shop: Includes prices, product availability and clear instructions for online ordering or visiting your store. Highlight convenient options you offer, like gift wrapping or local pickup.
Send reminders: Use SMS or email campaigns to remind customers about shipping cutoffs, holiday hours or last-minute gift ideas.
5. Get your e-commerce site holiday-ready
Before holiday orders start to pick up, walk through your online store the same way a customer would. Can shoppers find the right product, understand the total cost, and buy it easily?
A few tests and updates can help address problems before the rush.
Check your site speed and mobile usability: Open product pages, menus and your shopping cart on your phone as well as a computer. Look for slow-loading images, broken links or buttons that are difficult to tap.
Refresh product details: Make sure descriptions, photos, price and availability are accurate. Include dimensions, materials or other details customers need to choose a gift confidently.
Review payment options: Test the payment methods you already accept and consider whether additional options would be useful for your customers. Check processing fees and compatibility with your checkout system before you add new platforms.
Simplify checkout: Allow guest checkout whenever possible and remove any unnecessary steps. Show the shipping charges and other applicable costs before customers reach the final payment screen.
Make policies easy to find: Make your delivery estimates, holiday ordering cutoffs and return policies easy to locate on product pages and during checkout. Make it clear how customers can contact your company if they need help.
6. Hire extra help before you need it
The holiday season can stretch small teams thin. Hiring and training extra help before your busiest weeks can give employees more time to assist customers, restock shelves and fulfill orders.
Identify where you need support: Review last year’s busiest days and this year’s plans to determine which shifts and tasks need extra coverage.
Start early: Give yourself plenty of time to recruit, onboard and train seasonal employees before the rush hits. Give new hires clear responsibilities and make sure they know who to turn to with questions.
Hire coverage that can work when there’s demand: Workers available evenings or weekends may be a good fit for peak shopping hours. Confirm staff availability upfront, including the days after Christmas.
Review paperwork and coverage: Keep employee onboarding records and insurance documents organized. Review expected changes in your number of employees (even part-timers), products and inventory, sales volume and delivery operations with your insurer to determine if your coverage is sufficient for the season.
7. Cater to your customers (because they’re stressed out, too)
More shoppers in your store can mean more sales. But it can also mean more frazzled people juggling tight budgets and long gift lists. Here’s how to turn these challenges into positive experiences for your customers:
Make gift shopping easier: Create an online FAQ that covers delivery, tracking and returns. In-store, set up signage or a quick “gift help” kiosk with bestsellers, pre-bagged items and gift wrapping.
Stay reachable: Make sure your contact details and customer service hours are easy to find. If resolving a question will take time, acknowledge the message and explain when the customer can expect an update.
Set clear policies: Post return and exchange rules where customers can easily see them to avoid any misunderstandings.
Train your team for tough moments: Train employees on how to listen, explain the available options and identify when to involve a manager. Give them clear guidance on handling delayed orders, returns and other common concerns.
8. Create holiday cheer that motivates sales
A little holiday spirit can go a long way. Seasonal displays and thoughtful details can attract attention and make customers feel good about buying from you.
Add seasonal touches: Brick-and-mortar shops can string lights, turn on a holiday playlist or create a holiday photo spot for customers. For online stores, add a twinkling banner or festive product photos that make unboxing feel special.
Offer gift wrapping: Free or low-cost gift wrapping saves customers time and makes your products instantly gift-ready. Online sellers can include wrap options at checkout. Local shops can set up wrapping stations near the register.
Add a personal touch: Handwritten thank-you notes or a small seasonal freebie, like a candy cane, can help make customers feel valued and more likely to continue shopping with you.
Check your setup for safety: Inspect any decorative lights and cords for damage before use, and keep cords out of walkways. Check that in-store displays are stable and that extra inventory is stored securely.
9. Prioritize fulfillment: Know how to pack it, wrap it and ship it
A successful holiday promotion can easily go sideways if it doesn’t end with great fulfillment. Review your operations and fulfillment after the sale to ensure they’re ready for holiday volume and speed.
Provide realistic shipping details: Check current carrier deadlines and allow time for your team to process orders. Clearly distinguish processing time from transit time, and post estimated delivery windows and holiday ordering cutoffs.
Choose the right packaging: Select the right material to protect products in transit and keep costs in check. Look for boxes, envelopes or poly mailers best suited for product size and fragility. For delicate items, sturdy packaging may save you from costly damages and replacements later. Lightweight and durable products could benefit from slim mailers that can cut down on shipping fees.
Get realistic about your shipping management: If order volume is manageable for your team, pack and ship in-house. But if demand is going to outpace your capacity, look into third-party logistics providers or dropshipping partners who can help free up your resources and keep deliveries on track.
Add multiple, flexible options for product pickup and delivery: Some shoppers don’t want to wait or pay for shipping. Options like buy-online-pick-up-in-store (BOPIS), curbside pickup and local delivery can offer customers more flexibility.
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