< Back to blog

What would Herb do? What we can learn from the Southwest 2022 debacle


We’re just a few days into January 2023 as we write this. Hopefully, as you’re reading these words, you’re where you planned to be, comfortable at home or in your office. Not stranded in an airport somewhere. And you know where your luggage is. Or at least you’re reasonably sure when you can expect it to show up.

We stayed home in our mountain town of Telluride over the holidays. So everything we know about what happened with Southwest Airlines we learned from the news and watching the social media threads. But we do know that Southwest was uniquely affected by more than just the winter storm that blew across the country the week before Christmas. All the airlines were able to muddle through with minimal disruption. Southwest, however, was disabled on an epic scale.

It’s still too soon to know exactly what fell apart during those days that hundreds of thousands of passengers and crew are by now trying very hard to forget. The facts will emerge in due time. What interests us here is the business saga behind the human drama – how an airline so beloved for its value proposition of treating both employees and passengers with a merry kind of joy and, well, “luv,” as they have put it in their branding messages for decades, could strain to the point of breaking the very thing that sets it apart: the long-standing relationship between the business model and the humanity engaged with each other for almost 50 years.

Here's the brand message that put wind under the airlines wings since it began in 1971 (and we’re paraphrasing here): We’re cheap and scrappy. But we love you and we want you to be “free to move about the country.” We can continue doing it but only if you’re okay with the cheap and scrappy part. And we’ll make up for it by being fun. And we’ll treat you like a human being.

But last month, in 2022, as we watched the unfolding of events via the various social media posts (admittedly not all of them), we discovered a telling trend: the encounters between angry passengers and Southwest staff officially assigned to deal with them rarely concluded with anyone feeling better, more informed, or more respected for being humans who had somewhere they really wanted to go. Answers were official and unsatisfactory. Reactions were infuriated and frustrated. 


We noticed that there were a few instances where Southwest insiders stepped outside their official job descriptions to give their own insights into what caused the cascading calamity. And how they’re very truly, very personally so sorry for what it has done to the passengers’ holiday plans with their families. And how they’re stuck too, far from home in some staff lounge with Styrofoam coffee and vending machine food to keep them fueled. And their own phone calls to scheduling aren’t getting answered either. But there was no whining. No complaining. Just a human to human exchange of facts and experiences – as could be understood from the ground. 

The result of these kinds of exchanges? Everyone tapped into their own personal wells of empathy. The conversation transformed from one between angry passengers and abused, defensive staff into human beings feeling each other’s pain and wishing only the best for each other.

Human to human: Those are inklings of the old Southwest culture, still smoldering like embers, just a little bit here and there. But unmistakable. And absolutely revivable.

What Would Herb Kelleher Do?

We were especially moved by a post from a pilot who has been flying with Southwest for 35 years – which means he started with the airline when the company itself was just starting out under the founding vision of the irascible, unduplicable CEO, Herb Kelleher. If you were around in those days, we’re sure you still remember his wild, high-flying behaviors, that infectious ain’t-life-grand grin, the way he would show up unannounced randomly throughout the country behind ticket counters, at the baggage carousels, speeding passengers in wheelchairs to their gates. His leadership style was simple, no-nonsense, and yet memorable in every way. Who else could say proudly, while somehow gently mocking his competitors: Sure, “we have a strategic plan. It’s called doing things.” Perhaps Southwest’s best next steps were never better articulated than when he said "If you create an environment where the people truly participate, you don't need control. They know what needs to be done and they do it."

Kelleher’s subliminal message to the crew and employees was, “If I can be this crazy out of passion for our purpose, you’re safe to go to extremes too.” Safety was never compromised, of course. But caring was off the charts. And the stories from those wild, wonderful days are plentiful. And still in circulation.

Back to the pilot and his post: These stories are clearly still alive in his heart. Those fires of enthusiasm, joy, service, celebration that Herb had lit 35 years ago still glow deep within. He still has so much faith in the steadfastness of the Southwest culture of authentic caring that he even took the risk of signing his name, letting all the world (including Southwest HR) to see who wrote this 1,000 word essay explaining the entire situation from his historic perspective and deep well of institutional knowledge.

There was sadness and frustration in his voice. Absolutely. But there was also immense loyalty and earnest hope for the new CEO’s success to turn the company around to point its purpose back to the days when making air travel accessible and even fun for everyone who doesn’t mind the short-term hassle of no seat assignments.

What this pilot bravely shared with his readers was the perspective of a loyal, purpose-driven employee who has stuck with the company through all phases of its evolution, still intensely loyal to the initial spark of joy that Kelleher had breathed into an airline that was created from a sketch on a cocktail napkin. That pilot, whose job it is to go everywhere, isn’t going anywhere.

He is the keeper of the flame because his passion is working for a company where people matter. He fervently hopes that Southwest will return to that core value. And he’s got the stories to prove that it’s possible.

What Would You Do?

The word-of-mouth stories about Southwest that are still in circulation right now need to settle down and let the official investigations and after-action reports commence. But there are two things we know for sure right now:

  1. Culture-wise, there is agreement across all the stakeholders that Southwest has lost its way over the years, especially after the retirement, then passing, of Herb Kelleher. Where once the passion activated the purpose – which was to lift hearts and minds with accessible air travel – the perception now is that process activates another purpose – which is to get-them-on-get-them-off as soon and as cost-effectively as possible. Is that true? Investigations will tell. But perception tells its own story, which is just as harmful to Southwest’s health as any spreadsheet at this point.
  2. The stories of what’s good and true and beautiful about your company, no matter how old they might be, are still smoldering in the hearts of the true believers who still believe in your company.

Business models come and go. CEOs come and go. But the flame that makes your company great – for everyone associated with it – still burns in the stories and experiences and perspectives of the people who love your business most. Do you know who they are?

Success or failure will not be predicted by the quality of the ideas but how they translate in the hearts and minds of the people around you.

They’re the ones who matter.

Stay in touch. We want to hear from you!

Sending love and grounding. Take good care of yourself! 

Yours on the journey,



Awaken the leader within

Our sole purpose at Leadership Landing is to help leaders awaken great leadership within themselves and their organizations. Often that process starts with an idea.  Our blog explores questions and ideas that leaders face through the lens of the Five Attributes of Great Leadership. Come explore with us »

Recent Posts