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What Dallas CEOs Can Learn From Herb Kelleher

The charismatic chief executive set the standard for corporate culture and leadership.
Courtesy of Southwest Airlines
When Southwest Airlines hosted a memorial service for its co-founder and former CEO Herb Kelleher in January, more than 5,000 former Southwest employees and others packed into the arena at Kay Bailey Hutchinson Convention Center in Downtown Dallas. Because, of course, an airline is careful to not overbook.

“We had to find one of the largest venues in Dallas to accommodate all of the multitude of loved ones—friends, colleagues, and admirers,” Southwest CEO Gary Kelly quipped as he opened the ceremony. “What an extraordinary tribute that is to an equally extraordinary man.”

But this was no mournful, melancholy memorial service. During the two-hour celebration of life hosted by the company on behalf of its 60,000 employees and more than 135,000 alumni and retirees—whom Kelly affectionately refers to as the “Southwest Nation”—there were far more laughs than tears, as guest speakers regaled attendees with stories of the beloved former top executive. The corporate culture showcase, complete with a performance by a drumline, could best be summed up by one retiree’s vintage Southwest Airlines t-shirt, which read: “I don’t want to grow up—that’s why I work for Herb.”

“I’ve been told my passion and enthusiasm is contagious. … I hope so!”

Crayton Webb CEO, Sunwest Communications

Southwest’s charismatic leader was known for his over-the-top Halloween costumes and publicity stunts—like in 1992 when “Smokin” Herb Kelleher arm-wrestled the then-CEO of Stevens Aviation, Kurt “Killer” Herwald, in front of pom pom-shaking middle managers and cheering sales reps at what became known as Malice in Dallas. But it wasn’t only the PR stunts and crazy antics that defined Kelleher, nor was it his penchant for chain smoking and drinking Wild Turkey. It was his leadership success.

“I’ve always thought that Herb was our Winston Churchill,” Kelly said at the event. “Like Churchill, Herb always gave credit to the people of Southwest. And also like him, Herb was tenacious, and he never gave up. … There is no doubt there would be no Southwest Airlines without Herb. There’d be no freedom to fly. And, my, what a truly awesome gift he has bequeathed to all of us.”

Much has been written in business school textbooks about Southwest’s people-first corporate culture that Herb and his longtime sidekick, president emeritus Colleen Barrett, helped to establish. Southwest Airline’s own website describes the importance of having “a warrior’s spirit,” “a servant’s heart,” and “fun LUVing attitude” as three of its cardinal values: striving to be the best, following the Golden Rule, and being a passionate team player.

Management academics like Kevin Freiberg and Tom Peters point to Southwest’s family atmosphere and ability to inspire employees to a shared goal as the golden standard for corporate culture. (It should come as no surprise that Southwest Airlines has perennially been named to Inc.’s Best Places to Work list, and Fortune magazine named the airline the Best Place to Work in America in 1998.)

In Nuts! Southwest Airlines’ Crazy Recipe for Business and Personal Success, Freiberg and Peters write: “If Southwest’s corporate culture teaches us anything, it’s that employees and customers will love us for creating an environment where they can have fun. But the permission they get to loosen up must come from example. There is a spirit of liberty and freedom among people who don’t take themselves too seriously.”

Dallas business and leadership coach Lin O’Neill, who coincidentally spent most of her career with Southwest’s rival Continental Airlines, says she has seen a shift in management culture from one of authority to authenticity—a change she says millennials have helped usher in. Author of the book Managing High-Maintenance Employees, O’Neill says leadership today is learned on the job through firsthand experiences.

She points to a defining moment in her own career as an example she uses in teaching: “In the airline industry, if you came in on a Saturday and you were the supervisor when there was a snowstorm and aircrafts were grounded, you had to go through the seniority list in reverse order to find crew,” O’Neill recalls. “The only way that you could get out of it was having had alcohol within the past 24 hours. It’s an FAA guideline. So, I started down the list and called some folks who had joined us from other airlines. They knew the drill and would answer the phone, ‘Hi Lin, I’m just sitting here with a Bloody Mary.’

“So I call and I get this sweet, new flight attendant. Her name was Anna. I remember because it’s branded on my heart. … She said, ‘I’m getting married this afternoon.’ I was new in a supervisory role at the time and in all my youthful wisdom I asked her, ‘What time is your wedding?’” O’Neill ended up taking the evening route herself and now emphasizes the importance of putting humanity first in leadership.

In addition to compassion, management coach Christopher Meade is an evangelist for self-awareness. He espouses the importance of playing to one’s strengths and identifying personal weaknesses. “Knowledge and enlightenment is a very powerful thing when it comes to leading,” he says.

Dallas-based executive leadership coach Dale Young specializes in mentoring business leaders with an interest in leading with a higher purpose. His business coaching emphasizes leveraging Christian principles, and he “incorporates Bible verses in leading a company, if appropriate,” Young says.

Business consultant Lydia Epps, who oversaw human resources for about 1,000 regional Starbucks franchises, maintains that there is no one-stop shop for leadership. “People respond to different styles and techniques,” she says. “You have to find what works for you and your organization.”

If Southwest Airlines is any model, perhaps it all comes down to being real—just like Herb: “He was authentic,” real estate developer Craig Hall said at the celebration of life event. “In a time when so many people today put on pretenses and play games, Herb was refreshing.”

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