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New York Time's Article

wnbubbleboy

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In the 22 years since, Mr. Kelly, 52, has risen from financial controller to chief executive and has loosened up about what he wears to work. His administrative assistant, Gillian Kelley, has seen it. She pitched in last year when he was too busy to shop for the size 14 women’s high heels he had been wanting.

“Some pretty embarrassing Web sites we had to sort through,†Ms. Kelley said. She pulled the whole outfit together. And she added, grimacing, “The most awkward thing — fitting your boss with prosthetic breasts.â€

It had to be kept hush-hush, so that the 6-foot-3 Mr. Kelly could surprise the 2,400 workers at headquarters with his most outlandish Halloween outfit ever: Edna Turnblad, the bouffant mom from the musical “Hairspray.â€

Even in drag, oddly, Mr. Kelly was conforming — to a culture that has helped make Southwest the only consistently profitable company in the domestic airline industry. The episode last October revealed him as an unusual corporate chief these days, one trying to fit the mold of his company rather than trying to mold the company in his own image.

Indeed, as chief executives, owners and strategies shift rapidly at American companies, distinct corporate cultures — the sense of history, the best and worst impulses of an organization — are often swept aside.







http://www.nytimes.com/2008/02/13/business...ml?ref=business
 

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