Absurdly Driven looks at the world of business with a skeptical eye and a firmly rooted tongue in cheek. 

It seems like a good idea. 

Truly.

We're talking about Southwest, the airline that prides itself on caring for humanity.

So the notion of letting you know as soon and as conveniently as possible that your departure time has been changed is consistent with its brand.

But then there's the small matter of whether it works.

Last year, Southwest Airlines kept emailing me that my flight was delayed. 

I believed these emails told me the truth.

Until, that is the flight left without me and several others who were getting these emails -- which told them the plane wouldn't depart till much later. 

And, yes, it was the last flight of the night.

Southwest gate agents at LAX had no interest in helping, so we all had to find somewhere to sleep for ourselves.

Still, a couple of weeks ago I found myself booked on another Southwest flight. 

I took my seat on plane. But you know, though, that things can still go wrong.

So when the pilot announced that there were severe winds at San Francisco airport and the flight would be delayed, no one was entirely surprised.

It wasn't Southwest's fault, we knew that. 

We sat and we sat. 

And then I got an email from Southwest: "We wanted to let you know that your upcoming Southwest flight, Flight XXXX on June 15 from SFO, has a new departure time of 2.00PM. We know delays are frustrating, and we apologize."

Two things were frustrating about this.

One, the pilot had already announced many minutes before that we wouldn't be leaving before 2.30. 

And two, the email about my upcoming flight was sent at 2.01. That's a minute after the very same email said the flight was departing. 

It seems that nothing has changed since my last experience. 

The technology, however, wasn't done with making me ruefully chuckle. 

I soon received another email: "We wanted to let you know that your upcoming Southwest flight, Flight XXXX on June 15 from SFO, has a new departure time of 2.30PM. We know delays are frustrating, and we apologize."

Please don't worry. This wasn't sent at 2.31. It was sent at 2.30. 

So one email told me that the flight was leaving literally this minute (it wasn't) and another told me it had left a minute before. 

I asked Southwest why, oh, why this kept happening.

"We can understand your frustration," an airline spokeswoman told me. "Our goal is to create a positive travel experience for the millions of customers who choose to fly with us, but we've fallen short of that for you. We are continuously working to improve our technology and have a dedicated focus on enhancing our ability to provide customers real-time updates."

The last time this happened, a Southwest spokesman told me there had been a communication failure and the airline would, oh, improve its technology. 

This time, I'm told the technology is being continuously improved. 

It's been 17 months. And, as far as I can see, nothing seems to have been improved at all.

It might surprise you that United Airlines is trying to be in the forefront of fixing such things.

It's trying a new service called Every Flight Has a Story, in which it promises to tell passengers the whole truth a few minutes after the airline has informed Flight Attendants.

I know that Southwest means well, but at some point someone has to say: "Yeah, this isn't quite right, is it?"

On the way back, my flight was again delayed. This time, I received no email. 

Perhaps that's progress.

Published on: Jun 24, 2018