Leadership Lessons From Herb Kelleher

Let me begin by saying that that I loved Herb Kelleher. So much so, in fact, that I have had a hard time sitting down and writing this piece.

I wanted to process it all for a while before putting pen to paper. People who live big lives leave big, unfillable holes when they go. That’s just how it is. They are irreplaceable and one of a kind. If you have people like that in your circle, be thankful that you know them. I am thankful for Herb and the lessons we all learned from him about how to live a full and robust life while still building a thriving business. And, by the way, he had fun with all of it.

I discovered Southwest when I moved from North Carolina to Texas in 1985. They were a wonderful wake-up call for me.  No seat assignments, only peanuts and cokes on board, and flight attendants with humor and flair.  My devotion to Southwest was instantaneous and to this day it’s my first choice in carriers.

Their history is representative of their leader. They were daring, a small startup flying just one route between Houston and Dallas Love Field. Before long they grew into a regional powerhouse, then national, then international.

Unlike other airlines they were entertaining. There was a lot of joy and quirkiness. Flight attendants sometimes sang the pre-flight seat belt instructions, etc. Nobody seemed to miss the seat assignments, or TV’s or luxuries. They were there to get you from point A to point B as cheaply as possible.

And, don’t mistake all of the razzmatazz for a lack of efficiency. Just the opposite was true. They had efficiency down to a fine science. For example, they decided early on that they wouldn’t choose to fly into an airport where they couldn’t turn their planes around in 30 minutes or less. They also chose a fuel efficient model of airplane, the Boeing 737. Their efforts paid off. The planes I rode on through the years always seemed to be chock full. No wasted trips for Southwest with half empty planes. Maybe it happened occasionally but I never saw it.

Their motto was Love. How about that? Can you even suggest such a crazy idea in the hard data driven world of business? Love seems like such a soft science to build an organization on. But guess what? It worked!

And the love started at the top with Herb. He loved his people and his customers. He wanted to be called “Herb,” not Mr. Kelleher (As you can see, we are honoring his wishes in this article). Once, in the early days, when cash flow became a problem, his advisers suggested that he lay off some of his employees to save money. He rejected that notion out of hand and did something that lives in Southwest Airlines legend: he sold one of their airplanes and bridged the cash gap until their wheels were up again and they were flying high. I have heard it said that love is something you do. No better example of that than Herb Kelleher.

Herb was not a buttoned down, Mercedes driving CEO. He rode Harleys and he was known to kick back a drink or two from time to time. He dressed as Elvis. He would ride on his own planes just to meet people and see how things were going. Ever have him on one of your Southwest flights? Wherever you were going there was definitely going to be a party on the way. He was who he was and he was unapologetic about it. In fact, he reveled in it.

Which is why people loved working in his organization. He hired for individuality and then he nurtured and encouraged it. He wanted his people to, like him, be their true selves every day with every customer and every interaction. Win or lose, this is how we are going to roll.

Today, Southwest Airlines is a consistent powerhouse in an industry that has seen its share of turbulence. Southwest has consistently made money, expanded with success and careful deliberation, and become everything Herb dreamed of all those years ago when the first plane took off from Dallas.

Like Frank Sinatra, he did it his way and everybody who ever had the privilege of being touched by his endearing smile and can-do attitude is eternally grateful for it.

RIP, Herb Kelleher. You will be missed.