Absurdly Driven usually looks at the world of business with a skeptical eye and a firmly rooted tongue in cheek.
When you can't imagine what the world will look like in even a month's time, it's hard to know how to rebuild your business.
So how do you begin to attract customers back to your brand?
In a video to employees, he declared:
We will not be downsizing the airline.
Rational observers may have noted the passion behind such a statement, while also wondering whether his perspective was a little askew.
Soon, Kelly was offering more restrained predictions, admitting that the sudden drop in business was "breathtaking."
You might imagine, then, that Southwest would make as many cost-cutting moves as it could, bracing itself for a better tomorrow -- or a better some-day-in-the-distant-future.
Yet I opened my email on Tuesday to receive a quite cheery message from Southwest:
Ready for summer fares?
This was coupled with an enticement that one-way fares were as low as $49.
I hope I'm ready for a lot of things, but I'm not sure whether -- or even how -- it'll be safe to fly from, say, one state to the next, never mind to another country.
Here, though, was Southwest acting as if little had really happened and it was time for a regular old fare sale.
It's an interesting strategy. And, in its way, very much in line with Southwest's fundamentally positive brand.
For customers, however, it's an invitation to gamble. Yes, Southwest offers the advantages of not charging cancellation fees or change fees. Or baggage fees, for that matter.
If there's one airline that I'd be tempted to take my first flight post-virus it might, indeed, be Southwest.
But as I scanned further down the email, I could see Southwest promising that its planes now enjoyed enhanced cleaning procedures. The airline also encourages people to bring their own masks and hand sanitizer.
Somehow, then, it really isn't business as normal. And do I really want to get on a plane -- even for a couple of hours -- and wear a mask?
On CBS's Face the Nation, Kelly rebounded to optimism:
I don't think the risk on an airplane is any greater risk than anywhere else, and in fact, you just look at the layered approach that we use. It's as safe an environment as you're going to find.
Customers want to believe this. Until, that is, they read headlines such as: "Scientists find air travel is main driver of COVID-19 outbreaks."
I still admire Southwest's approach. It's a contrast to some of its rivals, which appear keen to protect only their shareholders and to treat their employees as if they're entirely disposable.
Look at United's telling some employees they're only part-time now, even though the airline has received its bailout money.
Normal times may not return for years, if ever.
I suspect, though, that Southwest's approach may at least maintain its emotional connection to its customers, while the likes of United will have to start from the emotional beginning. Yet again.