How is it already November?!?! While many are just starting to grok a fear of needing to reserve a Thanksgiving turkey (don’t forget people!), for those in retail, Holiday 2025 is already in full swing. Indeed, for most it began months, and even years ago.

I have the immense privilege of spending lots of time with many retail leaders, and while it’s only the first week of November, every retailer already has that focused look about them that says, “It’s showtime.” I thought I would share some of what I am hearing and seeing as folks focus on delivering their holiday plans.

 
1. Inventory Anxiety: The Great Retail Panic of 2025

Retailers are nervous about forecasting and inventory unlike any moment in recent history. Too much, and you’re the proud owner of 20,000 pairs of athleisure pants. Too little, and your customers are leaving sad, empty-handed TikToks about you.

Thanks to tariffs, supply-chain gremlins, and forecasting that’s basically “vibes-based math,” nobody knows if they’re overstocked or understocked — only that they’re stressed.

The smartest brands are focusing on how store associates handle these moments. When an item’s out of stock, do they freeze up — or pivot like a pro? Stores invested in growing and developing associates see teams who are nimbly turning “sorry, we’re out” into “let me show you something even better.”

2. The Calendar Crunch: Holiday Time Is a Flat Circle

Holiday shopping now starts somewhere around Labor Day, peaks in mid-November, dips the week before Black Friday, spikes again for Cyber Monday, and somehow still drags into January. So, for some retailers, the holidays are…just another season.

Every business has natural peaks, but the last few decades have seen the importance of “holiday” disappear (see: Prime Day in July). This takes the pressure off holiday to some degree, but it counterintuitively makes it even more important. If a retailer misses targets earlier in the year, the scaled back holiday season is the last moment to hit your annual numbers.

Here’s the truth: there’s no perfect timing. Shoppers are everywhere, all at once.
That’s why every interaction counts. The store is still the most powerful conversion engine — the moment a human being turns intent into purchase. And the best retailers know it. They’re using this season to make sure every associate is trained, tuned, and ready to deliver the kind of connection that no algorithm can replicate. Those moments and experiences carry brands well into the next season.

3. The Omnichannel Circus: Every Channel, One Heartbeat

Online, offline, curbside, app, drone delivery (okay, maybe not yet) — the modern shopper doesn’t see “channels.” They see one brand.

But behind the scenes? Retailers are juggling flaming chainsaws trying to make that seamless. I’ve seen store managers handling online returns, pickup chaos, and walk-in customers — all at once, with a giant grin and a Santa hat. This is the moment where the last mile matters most. Every in-store conversation is a performance review for the brand. And the best retailers are treating their associates not as clerks, but as brand storytellers, capable of turning operational chaos into customer joy.

Final Thought: This Season, Every Conversation Counts

If 2024 was the year of retail recovery, 2025 is the year of retail reality. Consumers are cautious. Costs are high. The margin for error is thinner than tinsel.

But here’s the upside: when everything’s on the line, execution matters more — and so does every human interaction in store. So, while everyone else is obsessing over discounts and inventory spreadsheets, the smartest leaders I know are obsessing over the customer experience. Because that’s where the real magic happens — one talk, one smile, one “let me show you this instead” at a time.