Southwest Airlines And The Parable Of The Ass-Kicking Line

“Have I ever told you about the ass-kicking line, son?”
 

My father appeared in the muddy foyer.
 

Drywall was delivered, not yet installed.
Trash was everywhere.
 

Bundle of shingles.
Two empty boxes of Vulkem.
Junction box knockouts everywhere.
Jr. bacon cheeseburger wrappers from Wendy’s.
 

My father stared at me while I continued sweeping.
 

The nice part of landing my first job out of college near my hometown was that I was close to family. My father could drop by unannounced and watch me perform my new role as a construction manager.
 

The downside to this geographical proximity was whatever was going to come out of my father’s mouth next.
 

“Fairly certain it’s in your contracts,” my father began, “for these trades to clean up after themselves. But, let me guess: given your inexperience and lack of credibility, these trades ignore you. In order to get the job done, you’ve simply decided to do it yourself.”
 

He continued.
 

“Probably bought that nice new broom with your own money. Right?”
 

Right.
 

“Well son, you’ve chosen to get in an ass-kicking line. You know what that is?”
 

I continued sweeping, head down.
 

“An ass-kicking line can be long. Or short. But at the front of every ass-kicking line is a large man with a giant steel-toed boot. When you get to the front of the line, he winds up and kicks you as hard as he can, right in the ass.”
 

I pushed my broom faster.
 

“Sometimes people quickly learn their lesson. They get out of that ass-kicking line. Other times people don't. They rub the seat of their pants and walk right back to the end of that line.”
 

I was hoping this was over soon.
 

“It appears to me, son . . .” my father paused for a dramatic finish, “that you are in an ass- kicking line. And if you find yourself in an ass-kicking line, you’ve got just one job: get out of that line.”
 

“Leading change when people don’t want to change is never easy. That’s why leadership is hard.”

Southwest Airlines was in an ass-kicking line.
 

It was a long line.
Really long.
So long it took years to get to the front.
 

Some employees were aware they were in a line. Others didn’t realize it . . . until a few weeks ago.
 

Then Southwest got to the very front of the ass-kicking line.
 

The week of Christmas—the busiest and most meaningful week of the year—Southwest cancelled nearly 17,000 flights. One of those canceled trips was my parents’ flight out of Denver that would unite the Hartmann family as we celebrated their 50th wedding anniversary.
 

Didn’t happen.
 

Plane was there.
Pilot was there.
 

No flight attendants.
 

The root cause was Southwest's outdated crew-assignment software, comically named Sky-Solver. Sky-Solver is a decades-old, off-the-shelf software application, built for legacy mainframe computing.
 

In 2019 on the GE Aerospace Blog, Senior Program Manager Kellie Kelley (yep—real name) noted, “The game-changing feature of this tool is . . . timely, reliable information is now available to relevant team members. With the push of a button, we have the data we need to make decisions every day to handle irregular circumstances.”
 

False.
 

As Southwest was using everything from Excel to crayons to the Hogwarts Sorting Hat to determine which crews should work which flights, COO Andrew Watterson said Sky-Solver wasn’t designed to solve problems of that scale.
 

Lauren Woods, the recently promoted (gulp) Chief Information Officer, commented that Sky-Solver works well with typical disruptions, but fails during “extreme circumstances.”
 

Snow in December—apparently beyond Sky-Solver’s capacity to handle “irregular circumstances”—now qualifies as an “extreme circumstance”?
 

It wasn’t extreme at American Airlines.
Or Delta.
Or United.
 

These airlines handled the highly predictable and common winter weather patterns well.
 

Southwest wasn’t a victim of extreme circumstances outside of their control. Its outdated technology platforms were, in fact, the cause of these extreme circumstances!
 

Southwest Airlines leadership—knowing their technology was outdated—decided to get in the ass-kicking line.
 

The assumption was it was a really long line.
And in a sense, they were right.
 

It was a long line.
But not long enough.
 

So why didn’t Southwest leadership act sooner?

Why didn’t they develop a plan and invest in a major technology update?
 

Probably for the same reason you and I don’t do the same.
 

Costs a ton of money.
Takes forever to implement.
Employees resist change.
It frustrates your customers.
 

In short: major technology updates change everything.
 

It’s signing up for immense pain and no short term gain.
 

It feels like committing to a major tech upgrade is itself opting to join the ass-kicking line.
 

And in a sense, it is.
 

Anyone who has ever been involved in a platform overhaul knows what that ass-kicking feels like. Not great.
 

But that’s what leaders do. Leading change when people don’t want to change is never easy. That’s why leadership is hard.
 

Leaders take their teams—drag them if they must!—to places they need to go.
 

Regardless of the annoyance and frustration.

Regardless of the ass-kicking.
 

Southwest CEO Bob Jordan said Southwest’s meltdown may push forward its plan for modernization. He then used an odd double negative that provided confidence to no one.
 

“I cannot imagine that this doesn’t drive changes to the plan.”
 

In-flight announcement from the cockpit, Bob: You’re in the ass-kicking line. So now you’ve got just one job: Get out of that line!

Over decades of relentless improvement, Southwest earned incredible trust from its customer base. Much of that evaporated over 72 hours in late December.
 

“I’m getting all my Pickleball pals to short Southwest stock. I’ll never fly them again.”
 

My father is still processing his anger.
 

I remind him he’s getting 25,000 mea culpa frequent-flier points from Bossman Bob Jordan. That’s a start to a decent apology, I say.
 

“You kidding me?” my father bellows. “They still haven’t fixed the system. It still snows in Colorado. What am I gonna do? Go back to Denver International and sit around all day for a second time knowing I may damn-well have the exact same experience again?”
 

I had an idea of what he’d say next.
 

“No thanks, son. Not getting back in that ass-kicking line.”
 

It’ll be a while before Southwest gets done sweeping up this mess.
 

You, on the other hand, can start now.
 

What technology updates—major or minor—require your attention, focus, courage, and leadership this year?