I want to tell you a story about an airline.

A few months ago I booked a flight on Air Canada. To say I have an axe to grind with them would be an understatement; I likely have a warehouse full of sharp chainsaws at this point.

Almost all of my complaints have to do with their online processes and policies, but sometimes it gets physical, like the time I found a staple in their kale salad. It poked a hole in my mouth, but I let the staff know, and slept it off on an intercontinental flight.

Plenty of minerals in that Kale. Don’t worry, the red is mostly strawberry.

I say this so you’ll understand that what I write is by no means nonpartisan. I have lots of issues with their pricing, service, loyalty programs, and more, fuelled by numerous issues over decades of travel. It’s become something of a running joke with my friends.

But this particular example is indicative of something more than my personal annoyances. It’s a concrete example of just how desperately companies need to modernize their processes.

William Gibson famously said, “the future is here, it’s just not evenly distributed.” Well, the past is still here, and it’s not evenly distributed either, but it lurks in neglected processes, voicemail hells, and outdated systems. It’s low-hanging fruit, and for many companies, fixing it will yield far better results than whatever shiny new project the CTO is enamoured with.

Air Canada’s an easy target. Their website breaks when you press the back button (in 2018!). And it constantly throws out gems like this one:

This is tremendously helpful.

So I want to dig into a recent experience a bit more closely, to see what’s broken, and how it might be fixed.

Last December, I booked a flight on Air Canada. The receipt for the purchase was sent to my gmail account . But apparently Air Canada had done something to itself flagged as spam, which meant the receipt went to my spam folder for 30 days, and was summarily deleted.

Now, my (entirely digital) accounting process involves forwarding such receipts to Expensify and Tripit when they appear in my inbox. Naturally, having them vanish is bad for my records, as well as for my expense reports and my pocketbook.

A couple of weeks ago I needed the receipt, and couldn’t find it. I search in vain using the six-character code in my inbox. Then I go to Air Canada and click on “my bookings.”

My upcoming flights. Plus the ubiquitous error seven. What’s error seven? I need to know!

This only shows upcoming flights, not past ones. No luck there, and nowhere to search for a flight by code. I surf around a bit and find this:

Easy! Show me my flights!

To my surprise I learn that this booking (for a flight I definitely flew on) has been cancelled:

Hi, I’d like a refund for EVERY FLIGHT I’VE EVER NEVER TAKEN PLEASE.

First I wonder if I’ve found a goldmine loophole by which I can fly for free all my life. Then I think that might be morally wrong, and that it just means you can’t find a flight from that code once it’s flown.

A bunch more clicking and interminable waits while the site reloads (it’s really, really slow) and I find, on the contact page, a form I can fill out to request a past receipt.

Shouldn’t this just be a list of flights?

Now, pretty much every other travel site has a way to look up past purchases. When you’re logged in, you generally get a list of past transactions. In some jurisdictions this is even mandated by law as a form of consumer protection. I mean, here’s United:

Note I can see a receipt for a past ticket, AND find a reservation by confirmation number, immediately.

I mean, it would be way easier for me to just click on a past flight and see my old tickets, but I’ll fill this out.

Except I can’t.

Ticket numbers only appear on the original receipt, not confirmations and check-in notifications.

There’s no way to search by six-character confirmation code. Oh, well, I guess I’ll click that box and enter all the required data.

But I can’t really do that, either. There are only options for one-way and round-trip; this was multi-city.

Multi-city trips need not apply.

Without a receipt I can’t find my ticket number. However, as I realize after thirty minutes of hunting through my inbox, in this specific case I’d requested (and not received) an upgrade—and that upgrade notice contained the ticket number. So by sheer wild coincidence, I have the ticket number.

My kingdom for a ticket number. Well, my expense report at least.

I enter it in the form, and await a copy of the receipt. Instead, I get this:

Wait, what?

I was expecting a bit more detail, or maybe them sending a mail to an email address on file. But not this. This sounds like humans. And yet everything in this process is digital, right?

Anyway, I wait five days, and get no mail. I even check spam. So I fill it out again. And wait.

A couple of days later, when booking a flight, their purchase process locks up. I book the flight again, and then notice two charges on my credit card. So I call them and get them to cancel one of the charges. While I’m on the phone, I say, “perhaps you can help me. I’m trying to get a copy of a receipt but nobody seems to be answering.”

“Oh, yes, that takes up to twenty-one days.”

“Really?” I ask, surprised. “The site says five.”

“Well, hang on a second and I’ll call them. When I send them a request it usually takes a couple of days.”

Them?

Anyway, a couple of days later I get a copy of the ticket receipt. And if you’ve read this far, well, let’s just say it’s worth it. Because after a human spends up to 21 days looking for a ticket number that’s in an electronic system, this is what you get:

Aren’t you glad you read this far?

This is an object lesson in innovation. There are so many customers, becoming infuriated by so many little things, wasting so much of their time, that simply making something basic work properly is a revelation to us.

When we wrote Complete Web Monitoring back in 2009, @seanpower and I learned that Southwest was consistently rated one of the best sites out there. It had big, ugly radio buttons everywhere. It was boring. It eschewed fancy design. But it worked. It was navigable, and rock solid. The pieces fit together.

Southwest had an advantage: It was an island. A renegade of air travel, it didn’t need to connect with partner airlines or other systems the way most airlines did. And that gave it an edge on simplicity.

In the past few years, we’ve seen very visible IT trainwrecks in the integration of large healthcare, payroll, insurance, and finance systems from both the public and private sector. Each is a perfect example of information siloes glued together by human APIs, and how they push all the work onto the consumer.

Many large incumbents — particularly those in monopoly positions; those that deal with high-priced products; and those heavily reliant on data and information — would be wise to put more emphasis on a delightful customer experience. That might not seem like the kind of leadership that gets on the cover of magazines, but it sure makes for less angry customers.

Oh, by the way, while filling out a form in order to write this post, I got a pop-up. Literally while typing in a field.

Yes, I need more time. I want the hours I spent trying to resolve this back, please.

Writer, speaker, accelerant. Intersection of tech & society. Strata, Startupfest, Bitnorth, FWD50. Lean Analytics, Tilt the Windmill, HBS, Just Evil Enough.