Colleen Barrett, You Were My Role Model for a Modern Elder.

May 29, 2024

Colleen Barrett, You Were My Role Model for a Modern Elder.

May 29, 2023

Thirty years ago, when I was a young, inept CEO of my boutique hotel company and we were about to take over our fourth San Francisco boutique hotel, I surmised that the only way Joie de Vivre could grow into a successful enterprise is if we invested in our culture. I defined culture as “what goes on around here when the boss is not around.” And, I realized as we grew the number of our hotels, I couldn’t be everywhere.

So, I wondered which corporate exec could teach me about culture and I thought about which company I most admired for their culture. Southwest Airlines was at the top of the list. So, I called Dallas, Texas with the intent of scheduling a meeting with the infamous Herb Kelleher (who ultimately served for 37 years as the CEO of Southwest). The company switchboard dispatched me to Colleen Barrett, Herb’s long-time executive assistant, who quite graciously told me Herb was “a little too busy” to become my mentor, but she encouraged me to write a letter to him asking a few questions about Southwest’s legendary culture.

Dutifully, I wrote a letter that afternoon asking Herb three questions. And, lo and behold, three weeks later, I received a letter back from what felt like Santa Claus with Herb complimenting me on my insightful questions, answering them, and saying that I could write to him once a year as his favorite topic was culture and he loved to cultivate young leaders. 

So, that’s how my ten-year pen pal mentoring relationship with Herb Kelleher started. But, I do believe after a couple of years, it was Mrs. Claus (Colleen) who was responding to my emails. And, Colleen went on to become the first woman President of a U.S. airline, becoming the Heart of the company (notice that Southwest’s logo has a heart and its stock ticker symbol is LUV). It’s a testament to Herb that he saw the potential talent of Colleen such that she could grow from legal secretary and executive assistant to become the President of the most valuable airline in the country. 

Earlier this month, Colleen took a Southwest flight to heaven as she passed on. During this Memorial Week, I just wanted to remember her as well as Herb. I was fortunate enough to be on the cover of Southwest’s in-flight magazine “Spirit” in January 2019 which was such an honor because the company and these two leaders have given me so much. It was that very month that Herb passed away. It’s because of modern elders like Colleen and Herb that I do my best to give back to young leaders who seek me out. 

-Chip

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