I’ve often told the story of my first meeting with Herb. Obviously, living in Dallas since 1970, I had read about Herb, and I had seen him around town. I knew people that knew and adored him, and I had great experiences with his airline.  I had met with and knew many CEO and Board Members by that point in my career. However, I wasn’t sure what to expect when I had my first meeting with Herb that day in 2001.

Gary Kelly, who is now the CEO of Southwest Airlines, was the CFO at the time. Gary cautioned me that Herb didn’t like computers in a people-oriented business and wasn’t too fond of formal presentations. So, I proceeded to his office with a pen and yellow pad in hopes that during our one-hour together we could connect on the subject of IT. We spent the first 15 minutes with him asking about me, my family, what I liked to do, my career. That was great and fun, but, I only had 45 minutes left to explain the importance of IT in a network business like an airline. And here’s how the rest of that meeting went…

I drew a few pictures about the customer experience on the day of flight, and we talked about simplicity vs. complexity. For every thought I would put down, he would launch into a story. I kept trying to bring him back to the point I was trying to make, but, frankly, we were both having such a good time that I kept forgetting what I was there to accomplish. Needless to say, I was a little shocked when we hit the 40-minute mark for the meeting and he said thanks – I’ve got it. I was dismayed, but Gary assured me that he did “get it” and would be supportive of an IT transformation.

Play it forward 10 years, Herb encouraged me to write my first book, Blind Spot: A Leader’s Guide To IT-Enabled Business Transformation. My first draft of that book was a very thick book about the importance of IT to business leaders. I brought it to Herb for review. His first reaction was to throw it in the trash. And, this is when I first really realized how special and unique he was. He took me back 10 years, back to that meeting in 2001, and said, “you need to simplify this like you did for me on your pad in my office.” He proceeded to recall and remind me of what I had scribbled down that day 10 years before. I had talked to him back then about how they managed the business of Southwest Airlines vs. how they managed IT. He actually recreated the comparison (see page 109 of The Blind Spot book) from his memory of our 40-minute meeting where I didn’t think he was paying attention. That’s pretty incredible. But, that is why Herb was Herb. He had an incredible ability to:

  • Absorb complexity and simplify it
  • Be present in the moment
  • Recall detail from years ago
  • Be fun to be around
  • Make you feel special
  • And many more great abilities…

This week I was honored to be invited to Herb’s Celebration of Life at the Dallas Convention Center. Thousands of people that he touched showed up. I have believed all these years that I had a “special” relationship with him. But, what was clear at this event, was that thousands of others felt the same way about their relationship with Herb.  The message was that we aren’t special, he was.

Author: Charlie Feld, Founder, The Feld Group Institute
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