Leadership Lessons from Herb Kelleher
This series of articles seeks to examine the character attributes of highly successful leaders, regardless of their adherence to a strong faith or moral standard. In presenting these thoughts, Leadership Ministries is not agreeing with or advocating these traits or practices, but rather presents these as ideas for discussion and development in your own leadership journey.
Herb Kelleher (1931 – 2019) was an American billionaire businessman as the co-founder, CEO and Chairman of Southwest Airlines. He was born and raised in New Jersey and went on to become a lawyer and clerk in the New Jersey Supreme Court.
Kelleher moved to Texas in 1967 intending to start his own law firm. Working as a partner at a Texas firm, he and a client, banker Rollin King, had the idea to begin a low cost airline to serve the Texas Triangle (Dallas, Houston and San Antonio). It took until 1971 to begin service and Kelleher’s early involvement was as general counsel. Following a number of challenging leaders, Kelleher was appointed full-time CEO in 1981, a position he held for 20 years.[1]
Keep it simple. Under Kelleher’s leadership, Southwest Airlines kept its strategy and operations simple in order to keep fares low. They only used a single type of aircraft, the Boeing 737. They don’t offer full meal service, even on longer flights. They avoided the hub-and-spoke schedule system of other airlines in favor of point-to-point traffic. They focused on secondary airports—like Chicago-Midway instead of O’Hare, and Orange County, California instead of Los Angeles International.
Herb Kelleher often worked the front line during busy travel seasons like Thanksgiving or Christmas, handling bags or handing out snacks on flights. Photo: Southwest Airlines
In the Christmas travel season of 2022, Southwest suffered a computer system breakdown that stranded thousands of passengers over the holiday. Long-time employees blamed the outage on a change in culture after Kelleher retired. Veteran Southwest pilot Larry Lonero said, “Herb Kelleher was… a very operationally oriented leader. Herb spent lots of time on the frontline. He always had his pulse on the day-to-day operation and the people who ran it. That philosophy flowed down through the ranks of leadership to the frontline managers. We were a tight operation from top to bottom. We had tools, leadership, and employee buy-in. Everything that was needed to run a first-class operation. Herb once said the biggest threat to Southwest Airlines will come from within. Not from other airlines. What a visionary he was. I miss Herb now more than ever.”
Hire the right people. Kelleher’s larger-than-life personality created a corporate culture which made Southwest employees well known for taking themselves lightly but their jobs seriously. At Southwest he created a “culture of commitment” devoted to the happiness of employees. He taught that happy associates would lead to happy customers, a differentiator in the airline industry. Kelleher said, “Your employees come first. And if you treat your employees right, guess what? Your customers come back, and that makes your shareholders happy. Start with employees and the rest follows from that.”[2]
Kelleher also wanted each customer to have a positive experience. He said, “What’s important is that a customer should get off the airplane feeling, ‘I didn’t just get from A to B. I had one of the most pleasant experiences I ever had, and I’ll be back for that reason.’” With this in mind, Kelleher put a premium on personality. “What we are looking for first and foremost is a sense of humor,” he said. The airline Kelleher founded and built has consistently been named among the most admired companies in America in Fortunemagazine’s annual poll. Fortune has also called him perhaps the best CEO in America.
Have fun. As the charismatic and colorful cofounder of Southwest Airlines, Herb was hardly a cookie-cutter chief executive. He showed up at company parties dressed as Elvis Presley, invited employees to a weekly cookout, handled baggage during the Thanksgiving rush, and brought doughnuts to a hangar at 4:00 a.m. to schmooze with his airline’s mechanics. He once arm-wrestled an executive from another company to settle a legal dispute and never hid his fondness for cigarettes and bourbon.
Always lighthearted and fun in his approach, Kelleher famously settled a legal dispute with another regional airline with an armwrestling match. Photo: Southwest Airlines
Herb said, “I think most of us enjoy fun, and why not at work as well as at play? And so, we’ve always encouraged people to be themselves, not to be robotic, not to be automatons. We don’t expect you to surrender your natural personality when you join Southwest Airlines. We want you to have some fun, we want you to have psychic satisfaction from your job. It’s not just about money, it’s also how you feel about what you’re doing. We want people to be recognized, participated, diligent and creative. And you can’t ask people to be someone other than themselves and have that kind of creativity and dedication and participation. So, we liberate people at work.”