LEGEND Spotlight: Gary Kelly

Gary Kelly

Chairman and CEO
Southwest Airlines


During your time at Southwest, how has your leadership style evolved and what motivates you as a leader?

I just celebrated 35 years as an Officer with Southwest, starting as Controller in 1986, then 15 years as Chief Financial Officer, and now 17 years as CEO, 13 as Chairman. With that progression, I’ve had to evolve from a functional leader to more of a general manager. I’ve had to rely less on my own subject matter expertise and more on judgement, commons sense, and especially other subject matter experts. I’m highly motivated by our Southwest Purpose and to take care of our People, our Customers, and our Stakeholders.

One of TBHF’s core values is excellence. How do you define “excellence” in business?

In business, excellence boils down to quality and value and relevance. Jim Collins says it well, you need three things to be successful: passion for what you do; strive to be the best at what you do; and make a profit. One could be the best in the world at something, but if no one wants it, it’s kind of irrelevant!

TBHF recognizes leaders who are transformational in business and their local communities. How does community leadership go hand in hand with business leadership?

It’s all about relationships, and Southwest is all about relationships. We want to connect and be a part of our Communities. Our Employees and Customers are in those Communities, so it enriches those relationships. We want to give back and invest our time and our treasure. As businesses, we have a responsibility and an obligation to support the places we serve, at a minimum.  

What advice do you have for business leaders about leading during times of challenge? In your career, how have you approached and overcome obstacles?

You just have to do three things: be prepared for tough times; be resilient in those times; and maintain a deep belief that you will find a way to fight your way through. We’ve faced many serious challenges during my 35 years: 9/11, the Great Recession, the pandemic. In all cases, we were financially prepared with a strong balance sheet and lots of cash to weather the storm. We supported our Employees with no furloughs, no layoffs, no pay cuts—and lots of frank information about the challenges ahead. Importantly, we communicated about our strengths, our plans, our determination, and our vision for the future once the challenge is met. It’s all about the Team and tirelessly and imaginatively attacking the problem. Failure cannot be an option!

What has been the most rewarding aspect of your involvement with TBHF?

I’ve enjoyed immensely getting to know the People and establishing some great friendships. It’s a wonderful organization with a great cause, and it’s been a rich and fulfilling experience for me, both personally and professionally.

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