Why Casual, Unscripted Chats With Customers Boosted My Margins Quietly

Last week, I spent 10 minutes typing a silly note to a regular who ranted in their order comments about their cat knocking over the candle they’d just received. I joked about my own cat’s obsession with knocking over my morning coffee, and asked if their feline had apologized yet. I didn’t think much of it until they replied with a photo of the cat wearing the custom bandana they’d just bought from my store, plus a link to their Instagram where they’d tagged us in a reel—driving 27 new orders in the next three days.

Here’s the first rule I live by: Ditch every scripted follow-up email you’ve saved. Customers can spot generic, copy-pasted lines faster than I can spot a bad margin deal. Instead, pull one tiny detail from their order or past interactions. If someone mentioned buying a dog bed for their senior pup, shoot a quick message a week later asking if the old guy’s finally sleeping through the night. It takes 30 seconds, but it makes them feel seen, not just like a checkout number.

Don’t be afraid to inject your own messy, unpolished personality into chats. I once admitted to a customer that I’d accidentally ordered 500 of the wrong mug design (yes, the one with the lopsided sun) and was using them as pen holders in my office. They thought it was hilarious, bought three of the “flawed” mugs, and started a fan group for my “imperfect” merchandise. Now, those lopsided sun mugs are my highest-margin SKU because people pay a premium for the story behind them.

But know when to dial it back. If a customer reaches out with a complaint about a delayed shipment, don’t lead with a joke about your cat. Fix the problem first—offer a refund, resend the order, whatever it takes to make it right. Once they’re calm, throw in a small personal touch, like mentioning you’ll double-check their next order to make sure it doesn’t go to the wrong warehouse. Overdoing the banter during a crisis makes you look like you don’t care, and that’s a fast way to lose a customer forever.

Finally, you don’t need fancy analytics to track this. I just jot down in a notebook which casual chats lead to repeat buys or referrals. The numbers aren’t even close—my repeat customer rate jumped 18% in a few months, and loyal customers don’t haggle over 10% discount codes. That means my margins stay fat, and I don’t have to waste money on expensive retargeting ads to win them back. It’s the kind of low-effort, high-reward trick that most sellers overlook because they’re too busy chasing flashy sales tactics.