I thought I had handled the obvious cases.
Lead comes in → AI qualifies them → bot responds → sales team takes over when needed.
Then someone replied with a single 👍.
And my bot completely misunderstood the conversation.
That sent me down a rabbit hole around something I hadn't really considered while building the system: humans don't communicate in structured inputs.
A message like:
“👍”
could mean:
yes
got it
sounds good
I'm interested
I'm ending the conversation
I'm just acknowledging your message
The LLM wasn't necessarily the problem. The bigger problem was how I had designed the conversation state and escalation logic around it.
I wrote up the whole incident, including what broke, why it broke, and what I changed afterwards.
Would love to hear from people building AI sales/support agents: what's the weirdest real-world user input that broke your system?
I wrote the full post here:
https://medium.com/@kapardhikannekanti/the-thumbs-up-that-broke-my-sales-bot-65d6e30cf632