Field Notes for Retail Leaders

For 25 years, my Thanksgiving ran on retail time. The night before Thanksgiving, my shift ran about 4pm to 1am. We re-merched the floor, processed shipment, sorted media kits that weighed 40 pounds, changed the windows, tagged accessories, and cleaned. So much cleaning. I got home at 2am, slept a few hours, spent some time with family, and went back to the store at 10pm so we could open at midnight. One of those openings, over 100 people were in line and I was the only manager until 3am. I...

Reader, Steve and I have done plenty of Substack Lives together, and this one is a fresh take. Come join us! Episode 1 of There’s Levels To This goes live this Friday, November 13 at 11am ET / 8am PT. Many people in retail treat a leadership level as a spot on the org chart. It’s the next job title to climb into. I know I did. But there’s more to it. Each level demands a specific way of thinking and brings a different weight of responsibility. Every level requires different parts of us. We’ll...

“Hey, Philly, you’re in charge of these cases now.” “Me?” He perked up. “Yeah, you. When you’re not helping anyone, unlock the cases and dust them. Make sure the watches are on the right stands and straight. Keep the sunglasses clean and organized. Then straighten the drawers underneath so we can find the boxes when we sell ’em. Cool?” “Totally! I’m on it!” That’s how I kept my cases clean. We cleaned every morning, but cases are hard to keep up. They’re one of the first areas to get...

One afternoon, late in the fall, I was running the floor. A rush came out of nowhere, you know how it goes. I was the only manager in the building, and everything landed on me at once. A cashier needed an override. A customer was on hold on the phone. The shoe department needed backup. FedEx had just rung the back doorbell. I was headed to the register when another customer asked me for a women’s shoe. I froze. My brain shorted out for a second, and I just didn’t have words. I finally got...

Just retail experience? Hang on now. I know soooooo many managers who call their leadership experience "just retail." When really — it's operations, people management, resourcefulness, and P&L ownership with no title attached. Get ready, because we're about to talk about knowing what your skills are worth outside retail because that makes you harder to squeeze inside it. Hiring managers outside retail don't read your vocabulary. "Shrink," "comp," "call-outs," and "floor moves" could very well...

Hey Reader, When I wrote The Retail Leader's Field Guide, this community built it with me. You told me what topics were missing. You fleshed out the outline. You told me what nobody else was teaching you — or what you wish someone had said sooner. I'm doing it again. Book two: The Analog Advantage: Advanced Leadership Skills for the Retail Leader Without a Field Guide. It's for the store and district managers who got promoted and then got nothing. No training, no mentor, just a bigger title,...

I overheard this on a retail floor last weekend. A manager, to one of his associates: "Thank you so much for your patience with that customer. You did a phenomenal job. Enjoy your break." That's it. That's the whole exchange. These seemingly small moments are what drives engagement and retention. They make you approachable. They make your teammates feel seen. When you do this regularly, you build a bench of talent. Corporate often builds recognition platforms for this like...

I couldn't make this photo smaller...I tried. This me in 2014, one year into my role at Tilly's. Sixteen years into retail by then. Leading a building through a remodel and double-digit comp increases, commuting 50 miles round trip, running on no sleep and too much iced coffee. It was also the year I found my voice as a leader. I learned how to push back on corporate and still get results. I developed leaders who developed other leaders. That's what really moves a business forward. When...

As a retail leader, I said no. A lot. I questioned new directives. Negotiated store hours against traffic patterns instead of the schedule template. Re-merchandised without asking. Ignored the forms that ate my time and did nothing for the floor. Asked to get dead merch transferred out before it sat there costing me sales. I also said yes a lot. Special projects, remodels, training new leaders, overnight shifts, covering a neighboring district when they were short a manager. That mix is what...