Most small business owners don't wake up thinking:
“Today, I’ll make my chatbot as creepy as possible.”
But still — it happens.
A visitor lands on your page, and the chatbot jumps in:
“Hi Rebecca, still thinking about that red cashmere sweater you added to your cart 3 days ago at 9:12 PM?” Yikes.
For a chatbot for small business, that’s the moment you either gain a customer’s trust — or lose it for good.
In the race to automate and compete with larger brands, it’s easy to overstep. The real trick? Use AI to help customers without making them feel watched.
A Real-World Cautionary Tale: When AI Crossed the Line
In 2023, a local pet brand launched a chatbot for post-purchase support. On paper, it was a great idea.
But a week into the rollout, something went wrong.
The bot began greeting users by name and referencing exact items they’d clicked on — before they even logged in.
Reddit threads blew up:
“Did this chatbot just call out my browsing history? 😳”
The fallout?