Every retailer knows the feeling: you spend most of the year telling yourself that a few of the store’s rougher edges will get smoothed out eventually. Then Black Friday shows up and “eventually” turns out to be right now.
Most of the year, stores can absorb a certain amount of friction. During peak, though, that gets much harder, and not only because there are more people in the store. Seasonal associates are still learning; digital order fulfillment is running in parallel with in-store traffic; promotions overlap; and inventory moves faster. Plus, the manager who normally steps in to untangle something is already tied up.
The friction was there in April and July too, but November and December is when little room remains to work around it.
The stakes are especially high during peak, as shown by the fact that more than 80 million consumers shopped in stores on Black Friday alone in 2025 [Source: NRF/Datapartners, August 2026). When that much demand is concentrated into such a short window, every bit of friction matters, especially the friction that gets between an associate and a sale.
The workarounds you stop noticing
Retail teams are good at making things work, which is a real strength; but it’s also how the more fundamental problems disappear from view.
Once associates learn a workaround, it becomes routine pretty fast. They know which screen to open, whose extension to dial, which manager to grab if a promotion doesn’t apply at the register. After a while, nobody’s really calling it a workaround anymore. It’s simply just “how things work here.”
For example, let’s say a shopper is looking for a gift in a size that’s sold out in that store. Ideally, the associate can see whether it exists somewhere else in the business and help the customer buy it right there. If finding that item requires checking a separate system, phoning another location, or (worst case) sending the customer home to search online, the retailer may still get the sale. But every extra step in that chain lowers the odds, and during the holiday period, that scenario is playing out all day, across every location.
That friction has a sales consequence: in Resonate CX’s US 2026 omnichannel research, “could not find what I needed” was among the reasons shoppers said they switched retailers. The opportunity for stores isn’t simply to know that an item exists somewhere in the business; it’s to give the associate a practical way to turn that inventory into a sale.
The pattern adds up in ways that go beyond any single lost transaction, as transactions slow down, and managers spend more of their day rescuing situations. Training often gets harder, because new hires now must learn both the official process and all the unofficial ones that stores have quietly built around the gaps.
The harder the transaction, the more ways stores need to sell
The easiest store transaction is a straightforward one: 1) the product is available, 2) the customer wants it, and 3) the associate rings it up. It’s a fine test of a POS on an average Wednesday, but not much of one for anything else.
Holiday brings far more variation, and that can quickly expose any gaps, especially since stores have to serve shoppers in person while picking and packing digital orders in the back. You may have scenarios daily like this: one customer wants to return something purchased online; another wants to ship an item to a different address with a gift receipt; a third needs a size that’s only available three states away. Meanwhile, a time-sensitive promotion has to apply correctly at the register, and the checkout line keeps growing while several associates are helping customers on the floor.
None of that is unusual for a specialty retailer, but what’s important is taking into consideration how much effort each of those interactions takes on the store side.
A few questions worth asking before peak season actually hits:
- Can stores flex checkout capacity with mobile POS when lines build, or is every transaction tied to a fixed register?
- When a size is stocked in another store or in the DC, can associates sell it from where they’re standing?
- Are cross-channel orders and returns part of the normal flow, or does each one still get handled as an exception?
- Do associates have enough customer context at the POS to actually deliver the service the brand is promising in its marketing?
On a basic transaction, most platforms may look relatively similar; but when stores have to handle several of these at once (which is, of course, exactly what November and December look like), the differences show up.
Shoppers notice these capabilities, too. Resonate CX found that 25% of consumers said better stock availability would make them visit stores more often. The technology question, then, isn’t just whether inventory is accurate; it’s whether stores can act on that inventory when a customer is ready to buy.
The sales you’ve inadvertently decided not to make
There’s a subtle version of the same problem, too: if a certain kind of sale looks too complicated, it often won’t even get offered as an option to the customer. That could mean a fulfillment option, a special-order process, consignment, an endless aisle transaction, or any number of selling models that make sense for the brand but don’t fit neatly into the systems already in place.
The cost here is easy to miss because there’s no bad transaction to point to; it’s just a transaction that never happens, filed away as too much trouble to support.
Put another way, flexibility is widely considered an operational benefit; but it can also be your most important revenue capability. Every additional selling model a store can support easily gives associates another way to say yes when a customer is ready to buy. The opposite is true, too: when the system makes a transaction too difficult to execute, the technology has effectively made a selling decision for the retailer.
Holiday is a useful time to look for these, because peak concentrates so many different customer needs in front of store teams over such a short window. What are shoppers looking for that the store can’t easily accommodate? Where are managers saying, “we can’t really do that here”? The answers tend to tell you quite a bit about whether the technology is supporting the way you want to operate or quietly setting the boundaries around it.
Plan for the hard days
Nobody is going to eliminate every difficult store moment before the holidays, nor should that be the goal. The more realistic aim is to strip out the unnecessary work that systems hand back to store teams, so associates have more ways to close a sale in the moment, and the customer experience holds together on the days that push hardest.
At KWI, we think store technology for specialty retail should ultimately be judged by how well it helps stores sell, especially when the transaction isn’t straightforward. A system that works beautifully for the simplest sale isn’t doing enough if associates lose options the moment the customer asks for something more complicated. We believe the system that works on an ordinary Tuesday needs to work even harder on Black Friday.
Stores should be able to keep selling even when transactions get complicated, without every exception turning into a manager intervention or a workaround. Store managers should be managing the floor, not acting as the human integration layer between disconnected processes.
Peak will always put more pressure on stores. The technology supporting them should make it easier to keep selling through that pressure, giving both store teams the flexibility to handle whatever the day brings and customers the experience they came in expecting.
AUTHOR BIO
Jennifer Baron is Head of Marketing at KWI, where she works at the intersection of retail technology, store operations and customer experience. She focuses on translating the challenges specialty retailers face every day into practical conversations about how technology can better support the people running and selling in stores. At KWI, Jennifer leads marketing across brand, content, demand generation and industry engagement, helping tell the stories of retailers navigating an increasingly complex omnichannel environment. She brings a B2B marketing perspective grounded in what matters most to retail teams: making it easier to serve customers, capture sales and keep stores moving.
