As he walked through weeds on the banks of the Snake River in Wyoming, Herb Kelleher could not find his boat. This was some twenty-odd years ago. Kelleher was then the maverick CEO of Southwest Airlines. He was taking a guided fly-fishing trip with his wife, Joan, a Texan whose mother was an heir to the massive A. S. Gage Ranch near Big Bend. But where was the boat?
Though a brilliant litigator and renowned executive, Kelleher was notoriously disorganized. Important papers were so likely to disappear in his desk that the drawers were kept locked. His car keys often vanished, as did his car itself. Finally, on that day at the river, he came upon a couple of twentysomething guides. “Which one is the Kelleher boat?” he asked.
The guides looked at him, wide-eyed. Their jaws dropped. Finally, one stammered out, “You’re Herb Kelleher. You’re our hero.” The guides were MBA students when they weren’t setting hooks for tourists. They’d studied the turbulent ride that brought Southwest Airlines into existence, and they were enamored with the company’s entrepreneurial moxie.
Kelleher, though, was flabbergasted. When he told me this story back in 2006 (well before his death in 2019), he said no one outside Southwest had ever called him their personal business hero before. “This was the only time that’s ever happened to me,” Kelleher insisted, waving around one of his ever-present cigarettes.
It seems surprising that Kelleher, whom Texas Monthly once named CEO of the Century, had never been venerated by a couple of strangers before. But it’s less surprising that the company Kelleher helped get off the ground still worships him. That’s evident in a self-published book Southwest is releasing today at the online Southwest the Store—the airline’s answer to Whataburger’s Whatastore. The book is called Leading With Heart: Living and Working the Southwest Way. It might as well be titled The Gospel According to Herb.
Over seventeen chapters, the book details Southwest’s corporate values, its leadership philosophy, and its strategies for hiring, adapting to market changes, and customer service. The book, written by (although not credited to) Texas Monthly contributor Loren Steffy, with the help of a corporate media group called History Factory, is dedicated to Kelleher and his longtime assistant turned Southwest president, Colleen Barrett.
Kelleher is quoted frequently. Sometimes his pronouncements come off sounding like commandments thou shalt follow at Southwest. In explaining why “there is no perfect knowledge,” Kelleher decrees, “Do not endlessly plan, discuss, and study in an effort to avoid the risk involved in actually making a decision.” The book also explains that—capital letters included—“Herb believed happy Employees make happy Customers,” although he also said that work at Southwest was “not about having fun,” but rather “about having fun while working very hard.”
Leading With Heart is more management tome than corporate history, but it does tell stories that some of those Snake River MBA students might have learned, like the time Kelleher arm-wrestled another airline executive for the rights to an advertising slogan, or when tiny Southwest bested big ol’ Braniff in a 1973 fare war by employing a brilliant gimmick. Fly on Braniff for their discounted price of just $13, or fly on Southwest for the full price—$26—and Southwest would give you a free fifth of whiskey.
That’s the kind of corporate lore that new recruits to Southwest hear during their training at “Southwest University,” and the book reads like a manual on how Southwest staffers should think. Then again, Southwest has plenty of good reasons to be preaching the gospel of Herb to its own choir, particularly at this moment.
The airline’s famously fun, familial corporate culture was rattled during the COVID-19 pandemic as revenue plunged, and Southwest posted its first loss in 48 years (the last one was just before the $13-fare war). Its two biggest unions—representing pilots and flight attendants—publicly griped that the airline’s management had veered from the “people-first” ethos that Kelleher is credited with creating in Leading With Heart. The heads of both unions told me last year that Southwest had pursued growth to the detriment of its people. They said employees were overworked and that the company hadn’t invested in enough technological upgrades to deploy the right people and planes to the right parts of the country to head off weather events and other disruptions.
All of that came to a head around the time of two holiday weekends in 2021, when thousands of flights were canceled and tens of thousands of passengers were stranded. Those problems were layered on top of difficulties in hiring enough workers (a familiar theme across the airline industry and the rest of corporate America), as well as a challenging work environment in which unruly passengers physically assaulted Southwest employees in airports and even on planes.
Southwest’s new CEO, Bob Jordan, told me on a couple of occasions that making amends with the airline’s employees was his top priority. And last week, when I spoke to Gary Kelly—Southwest’s executive chairman and the CEO from 2004 until Jordan took over in February—he said Jordan’s efforts to “love on our people” seem to be paying off. “Bob is very focused on strengthening our culture and reinforcing the values,” Kelly told me. “Knock on wood, but I’m really optimistic for the rest of this year. We’re going to be solidly profitable here in the second quarter, and that just makes all the difference.”
Leading With Heart was planned for release last June, as part of Southwest’s celebrations around the fiftieth anniversary of its first flight, on June 18, 1971. As with so many other things, the pandemic delayed the book’s release. Kelly told me the reason Leading With Heart leans on so many Herb-isms it that “you just can’t think about Southwest over fifty years and not think about Herb.”
Indeed, Kelleher’s chain-smoking, Wild Turkey–swilling, workaholic, laugh-a-minute persona was so associated with the airline, and vice versa, that Wall Street frequently fretted Southwest might fall apart without him. It didn’t. In the company’s first year in business, it was an upstart David that had two hundred people on staff and just three jets dogfighting with the industry’s established Goliaths. By the time Kelleher left the CEO post in 2001, the airline had ballooned to more than 31,000 employees and 355 planes. Then, without Kelleher at the helm, it got much bigger.
Today almost 60,000 workers operate a fleet of more than 700 jets, and the company carries more domestic passengers in the U.S. than any other airline. Southwest is a Goliath. That’s one reason why it seems a bit dubious for the book to conclude, “The culture that Herb established continues to define us.”
While it’s true that Southwest still flies one aircraft type and offers one class of service without frills, the airline long ago ceded its title as “the low-fare airline” to smaller carriers like Spirit and Frontier. Southwest was also once primarily a short-haul specialist. Thanks to bigger, more technologically capable Boeing 737s, Southwest’s route map now includes cross-country trips as well as service to the Caribbean and Hawaii. With all that growth and strategic change, one wonders if today’s Southwest is defined not by the culture Herb left behind but against it. The airline isn’t the same, so how could its culture be? “You can’t go through two generations and have nothing change,” Kelly told me. “Herb would be the first to say that if you don’t change, you’re going to die.”
But Kelly insists that the “people-first” ethos that Leading With Heart repeatedly hammers home has not changed. He explained that you can think of “people first” to mean management caring about employees or staffers caring about customers. “It’s about the Golden Rule here,” Kelly said. “It’s about treating people with respect and dignity and acting with civility. Those are really important themes here.”
The Golden Rule was first preached at Southwest by Colleen Barrett. She was the first to realize that Southwest needed to actively nurture its unique culture. She created a Culture Committee that was something of a roving band of apostles—composed of executives and those on the front lines—that traveled to various Southwest locations to spread the word about the airline’s history and values. Kelleher once told me Southwest’s culture “wasn’t something we came up with because we were geniuses,” but that thanks to Barrett, it was something Southwest decided to protect once it recognized it was an important asset.
Therein lies the rub about Leading With Heart’s claim that Kelleher “established” Southwest’s culture. He himself didn’t believe that to be true. And the book omits key figures who had a hand in fostering that culture during Southwest’s start-up phase, when competitors were trying to kill it in court and blow its planes—literally, according to Kelleher, in one case not mentioned in the book—off the tarmac. Most notably, the book seems to go through tortuous contortions to avoid using the name of Lamar Muse, Southwest’s first employee and first president, who came up with the booze giveaway. It was Muse who led the original band of employees into daily combat.
But Muse ended up resigning after a knock-down, drag-out boardroom fight with Southwest founder Rollin King. (King, by the way, is falsely credited in Leading With Heart with presenting his business plan to Kelleher on a cocktail napkin in a bar. King told me and others that much-repeated story never happened.) Muse went on to start a competing airline, Muse Air, and hard feelings lingered between his family (he died in 2007) and Southwest—which may or may not have something to do with an error in Leading With Heart. The book says Kelleher became CEO in 1978, after Howard Putnam left that role. In fact, Howard Putnam began in the CEO role in 1978 after Lamar Muse resigned. Putnam stayed with Southwest until 1981, when he left to try and rescue Southwest’s old nemesis, Braniff, from a financial tailspin. That was the year Kelleher became CEO. (If you want to get technical about it, Kelleher did serve as CEO in 1978, but only for a few months while Putnam was brought on board.)
These may be nitpicky concerns that most readers won’t care about in a management-philosophy book that’s unapologetically self-promotional and that touts cultural quirks such as the idea that every meeting should begin with “ten minutes of fun.” And, to be sure, it’s been a while since a management book has been written with this much detail about Southwest’s thinking. Nuts! Southwest Airlines’ Crazy Recipe for Business and Personal Success was released in 1998, and the 2005 book The Southwest Airlines Way also delved at some depth into the company’s strategy. But Leading With Heart tells the tale with more clarity than those earlier tomes and features many of Southwest’s current crop of C-suiters offering up the secrets to their strategic successes.
Still, it’s worth noting on the book’s release that Kelleher declined more than a few journalists’ advances—mine included—about writing a book that would tell his story and offer his thoughts on Southwest’s strategy. The reason, at least as he gave it to me: he didn’t want to act like he or his airline had all the answers. He didn’t want to be, he said, “messianic.” Does Leading With Heart come off that way? That depends on whether you think a messiah would proclaim: “Never rest on your laurels or you’ll get a thorn in your ass.”
