Field Notes for Retail Leaders

“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...

She's nice, but I don't think she has what it takes. That's what the regional manager said about me during my first store visit as a manager. Not to my face — to my boss, who told me later. I've heard versions of that sentence my whole career. A customer telling his daughter that college was the only way out of a job like mine. A guy at a conference who waved off an introduction with "yeah, we've already met" and turned back to the group. Someone who introduced themselves to a circle I was...

The break room Tiny chairs. Weird lighting. A shelf of extra denim stacked next to the mop bucket because nobody ever designed a place to put it. Maybe there's a second employee bathroom...nope. It lasted about six months before it became storage. Every store leader has stood in that room. Most of us have eaten lunch in it standing up. Last week I got on a call with Kevin Kelley — behavioral architect, co-founder of Shook Kelly, and author of Irreplaceable — for our Summer Break '26 ☀️ book...