How to Help Your Retail Staff Upsell Without Breaking Their Spirits

Retail staff are the unsung heroes of any store, juggling transactions, customer service, and—let’s be honest—the occasional drama with a smile that deserves an award. But when the pressure to upsell kicks in (extra items, fancy add-ons, or the “have-you-seen-our-membership” spiel), things can get a little overwhelming. Yes, increasing the spend per customer is great for business, but pushing your team without giving them the tools to succeed? That’s like asking someone to sprint uphill in flip-flops.

So, let’s make life easier for everyone. If you want your team to upsell confidently while keeping customers happy, you must set them up for success. Here’s how you can do just that.

Fix Your POS System, Seriously

You can’t expect staff to charm customers into buying more when they’re wrestling with a point-of-sale system that’s slower than dial-up internet. A clunky POS setup is a one-way ticket to customer eye-rolls and stressed-out employees. If transactions drag, freeze, or fail to accept various payment options, no one’s having a good time.

Enter the smart POS device from North—a solution that keeps things running faster than your most efficient cashier on their best day. Look for features like rapid card readers, clear and responsive screens, and software that doesn’t glitch out mid-transaction. A reliable POS system lets your staff focus on connecting with customers, suggesting add-ons, or quickly getting people through the line. Bonus points if you keep the system updated and provide training so everyone feels confident using it.

Keep Stock Levels in Check (and Stop Apologizing)

There’s nothing worse than a customer asking for a product and hearing the dreaded “Sorry, we’re out of stock.”

Okay, there is something worse: staff having to say it a dozen times daily.

Not only does it frustrate customers, but it also pulls staff away from more productive tasks—like upselling your perfectly paired products.

Stay ahead of the chaos with an inventory management system that’s sharp enough to track what’s in stock, what’s low, and when to reorder. Digital systems are great, but don’t skip regular physical checks, especially during peak times. Managers, this one’s for you—jump in and help when the stock count feels like a second job.

For bonus efficiency, use a display board or in-store tech to show customers if popular products are available. If they can see the “hot item” is in stock, they’re more likely to grab it without asking, saving time for your team and boosting sales.

Staff Your Store Like You Mean It

Look, no one wins when you’re understaffed. Customers wait forever, employees get frazzled, and the vibes go from festive to frantic in about three minutes flat. Understaffing doesn’t “motivate” anyone—it just burns out your team faster than a candle in a hurricane.

The solution? Smart scheduling. Map out your busiest hours, plan for peak seasons, and—if you’re feeling ambitious—overstaff slightly during the craziest times of the year. Too much help is always better than not enough. Build a roster with flexible team members who can jump between roles, and always have a backup plan for those “just in case” moments (because they will happen).

Most importantly? Listen to your team. They’re on the floor, so they know when the workload feels unmanageable. Adjust your staffing strategy based on their input, and you’ll strike a balance that keeps employees and customers happy.

Set Targets That Don’t Feel Impossible

Targets are fine. They’re great when done right—sales goals can motivate your team and give everyone something to aim for. But if you’re setting unrealistic goals that sound like a bad joke, you’re setting your team up to fail. No one upsells anything when they’re drowning in stress and wondering why they bother.

Instead, set goals that challenge staff but still feel doable. Offer incentives that get people excited to hit those targets—bonuses, team rewards, or even a simple shout-out can go a long way. Mix it with individual and group goals and clear the path to success. “Sell 10 of these items today, and you get a treat” feels much better than “Do better or else.”

Oh, and don’t forget the basics—enough staff, the right tools, and some breathing room. Your team can’t upsell effectively if they’re too rushed to even smile at customers.

Support Your Staff Like the Rockstars They Are

At the end of the day, your retail staff are the face of your business. They’re building customer relationships, handling complaints, and encouraging people to buy that one extra thing they didn’t know they needed. Give them the right tools, set realistic goals, and—above all—treat them like human beings, not sales machines.

If you get the fundamentals right now, you’ll see better results and happier employees during the busiest times of the year. A well-run store means customers leave with full bags and big smiles—and isn’t that what we’re all aiming for?

Featured image by Clay Banks on Unsplash