January 29, 2026

When Automation Goes Wrong

November 2025, by Kate Dunn, President of Evolve Sales Group

We all love automation… until it forgets we’re human.
A few weeks ago, I woke up with a head cold that made me sound like a congested foghorn. Unfortunately, it was also the morning of a physical therapy appointment here in Richmond, VA.

Like a responsible adult, I texted “CANCEL” to the automated reminder I’d received the night before.
Cue the chirpy auto-reply: “We do not accept cancellations at this time. Please call the office.”
Except… the office wasn’t open yet. So I left a voicemail explaining that I was under the weather.

The automated system allows for cancellations and rescheduling, but apparently not the night before a 7:00 AM appointment. So Hours later, when the team finally picked up the message, the cancellation window had come and gone — and so had my $95.

No malice. No bad intent. Just a system designed for efficiency that forgot to leave room for real life.
And it’s not just healthcare.

Panera recently began rethinking their kiosk-first ordering strategy after realizing something startling in a world obsessed with frictionless automation: when people are standing in your restaurant, a surprising number of them want to talk to an actual human. Go figure.

So it raises a few questions worth asking:
Where is the line between helpful automation and alienating automation?
The PT clinic’s system did its job — remind, notify, enforce. But it left me without a path that accounted for, well… being sick.

Are we actively listening to customers? Automation is fantastic when it reflects how people actually behave.
But when was the last time your team asked customers:
“Is this process helping you?”
“What’s frustrating?”
“What would you prefer?”

Are we building systems for edge cases or punishing them?
Sick days happen. Travel delays happen. Humans happen.

Here’s the takeaway:
Automation should make things easier — not colder, not stricter, not more rigid.
The companies that win are the ones who blend smart systems with accessible humans, and who treat feedback as an upgrade path, not an inconvenience.

Because at the end of the day, the goal isn’t efficient automation.

It’s an experience people actually want to come back to.

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