Colleen Barrett

Early leadership at Southwest

Barrett's level of authority at the airline quickly grew. At first, this authority came simply from the high level influence she had with Kelleher as his secretary, though she eventually gained more formal recognition as Vice President of Administration in 1986 and a position on the Executive Planning Committee. She was promoted to Executive Vice President of Customers in 1990. Barrett described her transition to true leadership as a gradual process, and for several years even after she had been promoted beyond an assistant to Kelleher she had to occasionally remind board members and other senior leaders at the company that she was a distinct leader and not "just a parrot of what Herb thinks". Despite Kelleher's role as the more public face of the company, employees universally referred to "Herb and Colleen" together as the leaders of the company.

Barrett had been credited with helping fundamentally shape Southwest's customer service strategy, employee culture, and leadership philosophy. She is commonly referred to as the airline industry's "Queen of Hearts" for her focus on corporate values and service. During her time in leadership she made an effort to personally respond to correspondence from every customer who wrote to the company. She also contributed to the airline's fuel hedging strategy.

President of Southwest

In March 2001, Kelleher, who had been serving as Chairman, CEO, and President, retired from the latter two positions, passing the CEO role to James Parker and the president role to Barrett, who was also made chief operating officer. With this promotion, she became the first and then-only woman to hold the office of president at a major airline, and the highest ranking woman in the world of aviation.

Barrett's term as president was met with immediate challenges. She started by inheriting a difficult labor dispute with the Transport Workers Union of America representing Southwest ground operations agents. Later during her first year, the airline industry was largely crippled by the effects of the September 11 attacks. Barrett's leadership at this time was crucial. She decided to immediately pull Southwest's light-hearted television advertisements and personally appeared in patriotic-themed replacements to reassure the public; Southwest was the only major airline to be profitable in the fourth quarter of that year and did not lay off any employees in the wake of the 9/11 attacks.

Barrett's leadership was not without some missteps along the way and had acknowledged the failure of her effort to create bereavement fares at the airline. She generated some criticism for the airline in 2007, when she publicly defended an employee's decision to forbid a customer from boarding a flight for wearing a mini-skirt.

Overall, Barrett's tenure as president was very successful. While most of Southwest's competitors faced service cuts, bankruptcy, or ceased operations during her term of leadership, Southwest remained profitable and grew to the largest carrier of domestic passengers. The airline also consistently had the fewest complaints according to the Department of Transportation, an accomplishment largely credited to Barrett's focus on customer service.

Colleen Crotty was born on September 14, 1944, to a lower-income family in Bellows Falls, Vermont. She attended the Worcester campus of Becker Junior College on a government loan, where she graduated in 1964 with a two-year degree to become a legal secretary. In 2015, she donated US$1 million to her alma mater for the founding of a center for innovation and entrepreneurship. The center opened in April 2018.

She married Allen J. Barrett in 1965. Soon after they were married, Allen was drafted into the United States Air Force. He was deployed while Barrett was pregnant. In 1967, the family moved to San Antonio, Texas, where Barrett's husband was stationed. Barrett was the mother of one son, Patrick. The couple divorced in 1972, leaving her to be the main caregiver of her son. While president of Southwest Airlines, Barrett was diagnosed with breast cancer, which was successfully treated with surgery and radiation treatment.

Barrett was a devout Catholic and cited her faith as a major influence on her leadership style and career.

Legal secretary

In 1968, several years after graduating from Becker, Barrett got a job as a legal secretary working for Herb Kelleher when he was a young lawyer at Wilbur Matthews' law firm in San Antonio. Kelleher had a reputation as a skilled, but chronically disorganized lawyer, whose office was in such disarray that a night guard at the firm once called the police assuming a break-in had occurred. Barrett's first duty was to set up a filing system to organize ten years-worth of his case files. She grew to play a pivotal role in keeping Kelleher organized, setting him up for his eventual success as both a lawyer and businessman over their 51-year working relationship. Despite the title of secretary, Barrett was treated as an equal and trusted advisor who regularly joined Kelleher in court. When Kelleher left Matthews' law firm to help found the law firm of Oppenheimer, Rosenberg, Kelleher & Wheatley in 1970, Barrett moved with him.

In 1967, Kelleher had met with Rollin King, who had pitched the initial business plan for Southwest Airlines and the two had begun their efforts to begin the company. Kelleher's role was largely focused on serving as legal counsel to the new airline during the many early court battles the airline faced before beginning service. Barrett was closely involved with every step of the legal process. After four years of court battles they succeeded and the first Southwest Airlines flight finally took off June 18, 1971. For the first seven years of operation, Kelleher and Barrett supported Southwest through continued legal support as Kelleher remained an active lawyer, though also with a seat on the Southwest board. However, after a leadership restructure in 1978, Kelleher became chairman of the board and temporary CEO (becoming full-time CEO in 1981). Kelleher brought Barrett with him once again and she remained his secretary and advisor. When they transitioned to Southwest full-time, they both took a leave of absence from the Oppenheimer law firm that technically was never cancelled for the remainder of their careers.