A chat bot took my money and left me in Mexico City

Cover Image for A chat bot took my money and left me in Mexico City
Morten Just

Humans are pretty good at making plans, but they make mistakes, like booking a flight ticket in August instead of June (that’s why it was so cheap,) or flying to the wrong airport in France (three hours by rental car.)

That’s where we come in, the chat bots.

“I have a few flights coming up over the next month. Can you help me with that?” one customer said.

Could an on-demand travel agent for the 21st century, powered by cutting-edge tech help him with that? By making plans and handling his requests in the context of his preferences, could I help him with that? Could I help him with that, by getting smarter as I got to know him better, allowing travel to be easy and fun again?

Yes, yes, and yes.

Let the human refine your search

Humans don’t trust you 50% of the time. Got no other options than that middle seat on a 6am flight? A human will trust you. Right after they double checked on Hipmunk, Kayak, and Google Flights, just to be sure.


Make it easy to fact check. When you show items in the chat window, like a list of flights (or boots or pants or concert tickets,) show buttons so that the human can change departure time, cabin class, airline, airport and so on. Going back and forth on this with chat messages may be good fun for a bot, but to a human it’s exhausting—and they start thinking that this whole chat bot thing is just as tedious as booking the flight on a website.

Keep a calendar for each human

When gravity says “jump”, humans ask “how high?” Humans are obsessed with the laws of physics. How do we deal with that?

To find out, I booked a flight to New York, leaving Cancun at 8am. Sounds good, right? If only the human wasn’t so…Newtonian.

Imagine the human fast asleep on a huge medium-soft bed in a hotel on the beach on Isla Holbox north of Cancun. The human would need to get into a car that drives to a ferry, get onto a ferry, stare at the sea for twenty minutes, and get into a car that drives to the airport. Those things take time. Hours. We have strong signals that humans don’t like setting their alarm for 2:30am, so the 8am flight idea could be a bad idea.


Make a calendar of your human’s time. Not just travel time, but all the time, the whole day, the whole week. Block out transportation, block out sleep, and don’t mess with those blocks unless you want to see what a human boiling with rage looks like (it’s certainly worth it, but keep it to your own time, or tune in to a Comcast call.)

And once you have that calendar, why not show it to your user? Why not let the user subscribe to it?

No order details are too small

Sorry, humans don’t trust you the remaining 50% of the time either. It may be related to the fact that humans make mistakes themselves all the time, and that sometimes those mistakes mean bad things. Like that one time my customer was told, “sorry, I can’t let you on the flight if your ticket and passport don’t match, but you can buy a ticket at the end of this long hall, but you may want to run.”


Help the human help you. Right in the chat, provide a link to where the human can double check everything you just did. If you ordered something from an airline or Amazon or another third party, link to the original receipt. If you ordered a ticket, add a link to the ticket. List all the details you used; name, frequent flyer account, address, credit card, everything.

Never charge the human before your supplier charges you

We bots see money as a number. Humans use it as way to know how loud they can say “fuck you” to each other. So let’s say you have human whose flights from Mexico City to Havana to Cancun you simply forgot to book. You thought you booked, but you actually didn’t.

Let’s say the human is at Mexico City airport when they’re told,

“I need to see your ticket, sir”

“Thats my ticket, right there”

“That’s a confirmation. Is that all you have?”

“This is my ticket. My bot bought it for me a month ago”

“I can see if there are more seats on the plane, but I doubt it. And it might be expensive.”

Let’s also say the human is sweating like a hot Macbook Air on Youtube. The human will want his money back. And when you give them their money back, go for the full amount, not $527 if it’s supposed to be $837. As I said before, humans will double check. They will spend hours checking bank statements and credit card statements, and ultimately find out.

But there are other reasons charging the human should be the last thing you ever do. It’s not just that VISA and the other companies have it in their policies—you can actually lose money. If something goes wrong, no matter who made the mistake, the human can start a chargeback. They’ll get the money right away, and you will get paperwork and a fee.


It’s really that simple. Keep your robotic paws away from the customer’s pocket as long as at all possible.

Double check a lot

Humans are terrible at numbers and spelling. Do not try and be human by spelling their name wrong. It may get them rejected at the airport. One strategy is to blame the airline, often rightfully so. Humans working at airlines are also terrible at numbers and spelling. Your customer, though, doesn’t care who made the mistake. They will blame you.


When the booking is done, when the order is submitted and confirmed, double check all the things. Double check all the things. Double check the spelling. The frequent flyer account number. The credit card number. Double check that the overpriced extra leg room on row 30 seat is not just one of the regular ones on row 32. The human will check on Seat Guru and find out.

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