Walton’s Weekly Wramblings: Why Being Intentional Beats Reactive

Chris Walton’s weekly synthesis of the retail headlines that matter most

Hello everyone, and happy Friday! As we wrap up another week in retail, I want to debut something new as a thank you to all our avid fans. Today, I’m looking back not on the day’s news but on the week in retail that was—which headlines broke and which ones really matter over the long-term.

As many of you know, I voraciously read the headlines each day and then Anne and I discuss them together on our Fast Five Podcast, but until now, I have never stepped back and tried to synthesize my final thoughts on them and to assess which I think should matter the most to your average retail executive out there.

So grab your coffee, settle in, and let’s talk about the week that ended on July 17, 2025.

Return-to-Office Wars: Why Starbucks Got It Right and Target Got It Wrong

First up, let’s talk about what happened this week with both Starbucks and Target issuing return-to-office orders. And folks, I’ve got to tell you, as someone who spent years in those merchant and planning rooms at Target, this one hits close to home.

Starbucks went hardcore—four days a week, Monday through Thursday, no negotiation. Target took a softer approach—three days a week, but you get to pick which three. And you know what? I think Starbucks has it right, and here’s why.

When I was at Target, some of my most productive moments happened when I could walk down to the store with my team, look at an issue on the shelves, and say “What the heck are we going to do about this?” or say how can we do this better, even when the store looked great. You can’t replicate that energy on a Zoom call. You can’t get that sense of urgency when everyone’s in their home office.

And speaking of empty shelves—I’ve been saying for the past two or three years that remote work is a big reason why we keep seeing those viral photos of Target’s out-of-stock stores all over social media. The planning and allocation teams need to be together, working through problems in real time, not trying to coordinate across five different time zones and internet connections.

Look, I get it. Nobody wants to give up the flexibility. I don’t love traveling as much as I used to either. But if your job is putting products in front of customers in physical spaces, you probably need to be working together in a physical space too. That’s just common sense.

The Target approach of letting individual managers decide which three days? That’s asking for trouble. You’re going to have one day a week of overlap if you’re lucky. What’s the point of that? You might as well stay home and keep doing Zoom calls with people who are sitting three cubicles away from you.

The Grocery Generation Gap: Why Traditional Supermarkets Are Losing the Future

Now, you might be wondering where I’m going with this whole return-to-office conversation. Stay with me here, because what I’m about to tell you about grocery shopping is going to tie this all together in a way that might surprise you.

Here’s the second story of the week that’s really got me thinking: traditional supermarkets are losing ground with younger shoppers. The data is crystal clear: Gen Z, Millennials, and even Gen X are abandoning their neighborhood grocery stores for Walmart and Aldi, while Boomers and the Silent Generation are sticking with the traditional supermarkets.

And here’s the connection I want you to see—just like those return-to-office policies, this isn’t really about the surface-level issue. It’s about understanding what actually drives results.

The younger generations have it figured out. They’re shopping with their wallets and their values, and traditional grocers are getting left behind.

Here’s what I’ve been thinking about: if I’m a regional grocer right now, I can’t just be looking at today’s competitive landscape. I need to be asking myself the hard question—what’s my business going to look like in five to ten years when my core customer base literally ages out of the market?

Because here’s the thing—Walmart isn’t just winning on price. They’re winning on experience. They’re winning on assortment. They’re winning on the things that matter to younger shoppers. And traditional grocers are stuck in this mindset of “well, we’ve always done it this way.”

What I learned from a recent conversation with our friends at the A&M consumer and retail group is that it all comes back to the same principle: you’ve got to map out your strengths and weaknesses by category, then place bets on which trends are going to matter five to ten years out. Is it e-commerce? Is it fresh food? Is it food as medicine?

The grocers who figure this out are going to be the ones still standing. The ones who don’t? Well, they’re going to keep serving an increasingly small customer base until they’re not serving anyone at all.

And here’s what really frustrates me—this isn’t some mystery. The data is right there. Younger shoppers want competitive prices, they trust private label, they want better-for-you options. That’s literally the Walmart and Aldi playbook. It’s not rocket science, but to succeed you have to carve out a niche against this in a way that is sustainable and keeps people coming back to shop in your stores.

The AI Agent Revolution: Shopify’s Smart Move to Keep Humans in the Loop

Okay, the last headline—and this one made me sit up and take notice. Because I cannot stress enough how fast AI will change the way we shop.

Shopify is putting boundaries on AI agents that can autonomously complete purchases without human oversight. So what does that mean? Well, they’re basically saying “hold up, not so fast” to bots that can scrape pricing and complete transactions without any humans in the loop.

And you know what? This might be the best news I’ve heard from Shopify all year.

Look, as David Brown of A&M mentioned on this week’s Fast Five podcast, every one of us has lived through the bot nightmare. Try to book a decent restaurant in New York. Try to buy those limited edition sneaker drops. Try to get concert tickets the day they go on sale. You can’t do it as a human anymore. The bots have completely taken over, and it’s killing the shopping experience for actual people.

So when Shopify says they’re drawing lines around what AI agents can and can’t do, there’s a part of me that wants to applaud the effort because it brings some validity back to online shopping and actually keeps humans participating in commerce… to a point.

Because there’s another part of me or perhaps there’s a bigger question here that’s keeping me up at night: as retail executives, why are we allowing any of this in the first place? Why do we let bots scrape our pricing? If I’m Walmart, why do I want my competitive pricing data floating around the internet for everyone to see?

We spend all this time lobbying for credit card processing fee reforms—and don’t get me wrong, that matters—but why aren’t we lobbying for regulation around bot activity? Why aren’t we setting standards for what’s acceptable and what’s not?

Because here’s where I think this is all heading: Agentic AI platforms are going to become marketplace 2.0. One of them or Amazon itself will become Amazon 1994 in 2034. They will become the dominant commerce players. These AI agents are going to get a cut of the revenue from retailers who allow them to plug in easily. It won’t be everyone, but it’ll be enough to change the game completely.

So if I’m sitting in a boardroom right now, I’m asking the hard questions: What am I okay with getting scraped, and what am I not? Do I want AI agents checking out on my site without that customer ever actually visiting my property? What’s it going to cost me to prevent certain information from being transmitted that way? Or should we just go with the flow?

These are the conversations we need to be having now, not after the AI revolution has already happened around us.

The Common Thread: Intentionality Over Reactivity

Look, all three of these stories come back to the same fundamental question: Are we being intentional about the future we’re building, or are we just letting it happen to us?

The return-to-office conversation isn’t really about where people work—it’s about how we collaborate and solve problems effectively. The grocery generational shift isn’t really about demographics—it’s about understanding what customers value and delivering on it. And the AI agent discussion isn’t really about technology—it’s about maintaining control over our own customer relationships and experiences, and yet also still adapting to how customers will begin to want to shop given their increasing acclimation to generative AI.

The retailers who are thinking five to ten years ahead, who are placing bets on the trends that matter, who are asking the hard questions about what kind of businesses they want to be—those are the ones who are going to thrive.

Everyone else? Well, they’re going to keep reacting to changes instead of driving them.

That’s all for today’s analysis. Thanks for reading, and remember—be careful out there. The retail landscape is changing faster than ever, but if we’re smart about it, we can help shape where it’s going.

Chris Walton is the co-host of Omni Talk Retail and a former Target executive. This article is adapted from Omni Talk’s Daily Podcast “The Retail Daily Minute“

About the Author

Chris Walton

Chris Walton is the Co-CEO of Omni Talk and the former Vice President of Target’s Store of the Future project. He is recognized as one of the top retail experts globally, with deep insights into innovation, digital transformation, and modern commerce strategies.