AI Hack #673: Negotiating With ChatGPT Riding Shotgun

Sometimes these articles write themselves. If you’re anything like me, you just spent the last week or so either hosting a lot of people at your house or mooching off someone else’s hospitality (Team Clifford did the latter). Whether your family’s all in the same town or spread out, it all involves complex logistics around the holiday season. This year was no different for our family. My oldest son just started his freshman year at Syracuse University, and we flew him home on Delta for his Thanksgiving break a week and a half ago. I’d intended to fly him back myself in a small airplane the Sunday before his classes began on December 1. Of course, as luck would have it, Mother Nature had other plans for us in the run-up to our Sunday departure. To reduce stress, I decided to book my son on a commercial flight back from Washington, D.C. to Syracuse instead of worrying about whether or not the Cessna 172RG would make it through the ice.

AI Assistance — Illustration by Hongwei Jiang/Getty Images

All seemed to be going according to plan until the first JetBlue delay notice hit my inbox. You know the nauseous feeling that those delay notices induce and they’re usually the harbinger of more bad news.

The revised itinerary only gave him a 20-minute buffer to connect to his Syracuse flight, which seemed wildly unreasonable. I was surprised that they even booked the connection. I quickly scanned and saw a Delta flight that was still delayed, but looked a little more of a safer bet, so I rebooked that.

I turned my attention back to the process of securing a refund with JetBlue, which I knew might be challenging because I booked, of course, the lowest tier, basic economy ticket they had, not thinking we would ever need to cancel it.

I hopped into the JetBlue support queue through WhatsApp and started chatting with them. Sure enough, after a long hold, I was greeted with somebody who told me that they could give me a future travel credit less $100, but not a refund to the original method of payment. I could feel my face turning red as my anger began to simmer.

Also by Henry Clifford: Here’s Why Your Employees Quit

I sometimes wonder why I get so mad during frustrating customer service interactions. A big part of it is because we know, as integrators, our customers wouldn’t tolerate any sort of treatment like this. Maybe it’s because we treat our customers so well that they keep coming back to us because they get treated this way by large corporations.

A thought hit me in the middle of this chat: Maybe I should really be live-pasting this chat into AI in a bid to get some perspective around how to respond (besides my usual tricks like “let me speak to a supervisor”)? After all, I originally discovered the alternate flights and modeled through the alternate situations by asking AI about it. Why wouldn’t ChatGPT be a good negotiating partner? Sure enough, I pasted in the interaction, and AI came back immediately with a boilerplate piece of copy to paste into the chat using FAA language to state why I was owed a refund to my original method of payment.

Here’s a direct transcript from the AI session with ChatGPT:

Henry — you’re doing exactly the right things, and you’re making the right arguments, but JetBlue is giving you the scripted, lowest-authority answer.

Let me break down what’s happening and how to win this.

1. JetBlue’s Agent Is Wrong About the 3-Hour Delay Rule

JetBlue is applying the “< 3-hour delay = no free cancellation” rule that applies to point-to-point flights, not connections.

But your problem isn’t the departure delay. Your problem is JetBlue sold an illegal (or near-illegal) connection that became impossible due to their own delay.

JetBlue’s Contract of Carriage gives you rights here.

If a schedule change causes you to miss your connection, or materially changes your itinerary, you are entitled to a refund.

Not travel credit. Not a $100 fee. A full refund.

This is standard across airlines.

You are arguing the correct principle:

“The schedule change made the itinerary unusable.”

1. The Agent Isn’t Understanding the Key Point

They’re stuck on:

“The flight delay is less than 3 hours.”

But your correct response is:

“This is not about the delay.
It is about JetBlue’s delay making my connection impossible.
JetBlue cannot require a customer to take a trip itinerary that no longer works.”

You already started articulating this — but we can sharpen it.

1. Your Strongest Argument (Say This)

Copy/paste this EXACTLY into the chat:

“JetBlue’s delay made the connection physically impossible to make. This is a material schedule change. JetBlue’s Contract of Carriage states that if a schedule change or delay makes the itinerary unusable, I am entitled to a refund to the original form of payment. I am not refusing the trip — the trip is no longer operable due to JetBlue’s change. Please escalate to a supervisor.”

If they push back, follow with:

“This is not a voluntary cancellation. This is involuntary because JetBlue’s delay prevents completion of travel as ticketed. Please process a full refund or escalate.”

1. If they STILL push back — add the nuclear line

This gets supervisors involved immediately:

“If this cannot be resolved here, I need written documentation of refusal so I can file with the DOT. Under DOT rules, passengers are entitled to a refund when an airline’s delay prevents them from completing their scheduled itinerary.”

Airline agents become very flexible when “DOT” shows up.

The chat went dark for a few minutes, and I asked if they were still there (“Yes, absolutely. One moment please,” they responded). Within 30 seconds, I saw a cancellation email come through to my inbox. The agent immediately said that payment in full would be refunded back to my credit card. I felt elated, supercharged, almost like I had some sort of magical power. I wanted to share this experience with you because it’s the beginning of the holiday season, and I’m sure you’ll have some travel shenanigans in your future where something like this might come in handy. Think about conversations with vendors or customers. Having the AI there live to give you feedback isn’t intellectually lazy. It just gives you other options to consider. I never in a million years would have figured out that boilerplate language to paste into the chat that magically created that refund scenario.