Every holiday season brings new challenges. This year, many retailers are preparing for the latest impact to stores: customers who have already done much of their shopping research before they walk through the door.
More shoppers are using AI tools like ChatGPT, Gemini, Claude, and Perplexity to compare products, research brands, and narrow their options before deciding where to shop. According to an Attentive survey highlighted by Retail Dive, two-thirds of consumers, and 80% of Gen Z shoppers, have used AI to help make purchase decisions in the past three months.
In other words, this holiday season is likely to be the first where AI-assisted shopping is firmly in the mainstream for brick and mortar stores, not just e-commerce.
For specialty retailers, that doesn’t make the store less important, but it changes what customers do and what they expect once they get there.
Shoppers arriving with a shortlist isn’t new: ecommerce, ratings, reviews, referrals, social media and endless access to product information have been shaping store visits for years. What’s changing is how quickly and deeply shoppers can research before they ever walk through the door.
AI gives customers another way to compare products, narrow their options, and ask increasingly specific questions. So, by the time they reach an associate, they may already know what’s available, what reviewers think, and which products they’re considering.
Every major shift in retail over the past few decades has changed customer expectations: E-commerce raised the bar for convenience, and omnichannel raised the bar for flexibility. Mobile technology raised the bar for speed, and now, AI is raising the bar once again. For retailers, the challenge this holiday season isn’t simply adopting AI; it’s making sure their stores are prepared for customers who are more informed and have even higher expectations.
Holiday shopping is also starting earlier than ever. Research shows that 71% of shoppers begin their holiday shopping before Black Friday, and nearly half begin before November. That makes this a planning conversation for today, not a problem to solve in the middle of peak season.
Here are three areas retailers should focus on before peak season:
- Help Associates Answer Smarter Shoppers
Store associates have always been one of specialty retail’s biggest advantages, and AI makes their role even more valuable.
What’s changing is the type of conversation they’re having now.
For example, instead of asking, “What’s your best-selling sweater?” a customer may now ask where one sustainable fabric is sourced, whether a style is worth the investment, or how one brand compares to another. Those questions often reflect research they’ve already done with AI before they arrived.
Associates don’t need to compete with AI in 2026, though. They need to be ready to build on what the customer already knows.
That starts by giving them access to the same product information customers are already finding online. Fabric details, sizing guidance, care instructions, styling recommendations, inventory, and purchase history shouldn’t require searching through multiple systems or tracking down another employee. The information should be available when the conversation is happening.
Just as important, associates should be equipped to provide the context AI can’t.
They’ve helped customers with similar needs and they know which styles consistently fit differently than expected. They know which pieces become customer favorites after a season of wear and which products pair naturally together, and they understand the preferences of their local clientele in ways that AI never will.
This is where specialty retail has an advantage.
Technology should help associates spend less time looking for information and more time building relationships. The question to consider ahead of holiday season this year is:
Are your associates spending more time hunting for information, or more time selling and creating relationships?
The answer often says more about the customer experience than any satisfaction survey ever could.
- Make Sure Your Stores Can Deliver
If a customer walks into your store expecting a product to be available, associates need to answer that question immediately. If it isn’t available in that location, they should be able to locate it elsewhere, ship it directly to the customer, or offer another option without losing the sale.
A few years ago, shoppers often came into a store hoping to find the right product. Today, they’re more likely to arrive expecting you’ve already got it.
Associates should have real-time visibility into inventory across every store and the distribution center. They should be able to save a sale with endless aisle or ship-from-store when an item isn’t available locally. They should also be able to complete checkout wherever the conversation happens instead of sending customers to stand in another line. And they should have access to the customer’s purchase history so they can make informed recommendations instead of starting every interaction from scratch.
When AI recommends a product that your store can’t find, the customer doesn’t blame AI. They leave wondering why the shopping experience didn’t live up to the expectation. You should also be checking how your stores answer this question:
If a customer walked in today after asking ChatGPT for a recommendation, could your associates confidently help them complete the purchase, even if the product wasn’t sitting on the shelf?
If the answer is yes, you’re in a strong position heading into peak season.
If the answer is no, you’ve just identified the first place to start.
- Give Customers an Experience Worth Talking About
Retail has always been driven by word of mouth.
Today, those conversations happen in more places than ever: customers share reviews, post videos, recommend stores to friends, and describe their experiences across social media and online communities. Increasingly, those same conversations influence the recommendations AI tools provide to future shoppers.
What customers remember from a store visit, and what they talk about, are typically things like:
- An associate who remembered their name.
- A recommendation that turned out to be exactly right.
- An easy return.
- A follow-up message that felt personal instead of automated.
- Finding the perfect gift after someone took the time to understand who they were shopping for.
Those events build loyalty because they feel genuine, and they’re the kinds of experiences customers naturally share with others. Technology should give associates more time and information to create experiences like these, not get in the way.
It’s difficult for competitors to copy a memorable customer experience; it’s even harder to compete with a retailer that’s known for consistently delivering one.
The Bottom Line
After more than 40 years working with specialty retailers, we’ve seen one thing remain remarkably consistent: the retailers that succeed are the ones that adapt as customer expectations evolve.
For retailers, the real impact of AI this holiday season may be less about how they use it and more about how their customers do.
While the way customers prepare before entering a store has changed, how retailers anticipate and respond to those changes will be key to success this season.
About KWI
KWI builds and supports the systems that make retail work. For over 40 years, retailers and brands have grown with KWI, relying on its platform for Point of Sale, Order Management, and Merchandising, along with a full suite of omnichannel capabilities including loyalty, e-commerce, and more. Built for where retail is going, not just where it’s been, the KWI platform is designed as one integrated system for multi-location specialty retail.
Retailers and brands don’t just implement KWI. They build on it, season after season, location after location, backed by a team that stays with them long after go-live. KWI is headquartered in Melville, NY.