Back from Canada Day with a cautionary tale about what happens when automation goes hilariously wrong.
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I found a car online last month. It looked perfect, so I filled out the “check availability” form. You know, just seeing if it was still available.

I got an INSTANT response. Within seconds, I had three texts, two emails, and a voicemail minutes later.

“Hi Noah! Ready to come see YOUR new car today?”

Except here’s the thing... in between all those messages the car had been marked as sold and I did get one actual human message confirming this.

But then, for the next FOUR WEEKS, I kept getting daily messages asking when I wanted to “finalize paperwork” and “take delivery of my vehicle this weekend.”

I tried everything:

I called the rep. Voicemail.
I left a message. Nothing.
I sent emails saying “this car is sold.” Crickets.
I texted back “STOP” and “This doesn’t exist.” More messages.

But my favorite response? When I finally got through to someone, they said: “Oh, our system is automated.”

Thanks. I figured that out when it kept trying to sell me a ghost car.

Here’s what gets me:

This dealership has every piece of fancy tech. AI-powered CRM. Automated follow-up sequences. Lead scoring. Smart routing. It probably cost them millions.

But nobody thought to connect their automation to their actual inventory.

So while their system was firing off “come get your car!” messages, the car had been gone for weeks. And there was no human who could stop the madness.

The Hidden Cost of Bad Automation:

Every business thinks they’re saving money with automation and looking at how to AI everything. But here’s what this dealer lost:

• A qualified buyer (me) who was actually interested
• Every future car I might have bought
• My entire network’s business (because you know I’m telling this story)
• The time their team spent on a deal that couldn’t exist

All because their high-tech system couldn’t answer one simple question: “Does this car still exist?”

The High-Tech/High-Touch Playbook (Whether You’re Automated or Not):

If You’re Already Using Automation:

Map your customer journey. Every touchpoint. Ask yourself:

Where does automation make things faster/better?

Where does it make things worse?

Where are customers getting stuck or frustrated?

If You’re Exploring Automation:

Start with ONE thing. Not everything. Pick the most repetitive task that has the least emotional component. Maybe appointment confirmations. Maybe order updates. Maybe FAQ responses.

But here’s the key: Build in these safety nets from day one:

1. The Context Check: Before any automated message goes out, can it verify the information is still true? (Inventory exists? Appointment still available? Offer still valid?)
2. The Escape Hatch: Every message needs a clear path to a human. Not hidden. Not complicated. “Need help? Reply HELP or call [number].”
3. The Stop Mechanism: When someone says stop/wrong/mistake, the automation should pause and alert a human. Period.

The 3-Touch Rule That Works:

Whether automated or manual, here’s what actually converts:

Touch 1: Acknowledge quickly (within 2 hours)
Touch 2: Add value (share something useful about what they inquired about)
Touch 3: Check temperature (“Still looking? Anything changed? How can I help?”)

After that? Stop pushing. Start helping.

The Million Dollar Question:

Before you automate anything, ask: “If this goes wrong, how mad/annoyed/frustrated will my customer(s) be?”

Low stakes? (Order confirmation) → Automate away
Medium stakes? (Appointment scheduling) → Automate with human backup
High stakes? (Complex sales, problem resolution) → Human first, automation assists

The Truth Nobody Tells You:

You can’t automate relationships. You can only automate transactions.

The companies winning right now during the AI revolution? They use automation to free up humans for human stuff. Not to replace them.

Talk soon,
Noah

P.S. That dealership? They’re still texting me. Six weeks later. But here’s the thing - ONE phone call from a human who said “Sorry about that, let me help you find what you’re looking for” could have maybe saved the sale. Instead, I’ll keep driving my other car.

P.P.S. Ready to get this right? A couple big announcements coming about building systems that amplify what makes you human instead of hiding it. This is going to change everything about how we think about AI and relationships. Stay tuned. 🚀

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