A CEO in drag? That and more as Jeff Bailey dives deep into Southwest Airlines

After seeing the photo of Southwest Airlines CEO Gary Kelly dressed in drag, Jeff Bailey was sure he was onto something interesting.
Really, how could any reporter pass this up?
In the photo, Kelly, who stands at 6-foot-3, had situated himself inside one of Southwest's cockpits and was draped in a pink sequenced dress and high heels. His outfit was topped off with a bouffant wig as he desperately tried to pass for Edna Turnblad, the housewife star of Hairspray.
The Halloween costume gave Bailey, a business reporter for The New York Times, a glimpse into the airlines colorful CEO and eventually led to his story, "Southwest. Way Southwest."
The story details Southwest's unique culture, one that has helped it remain "the only consistently profitable company in the domestic airline industry."
Bailey, who has covered airlines for The Times since 2005, tells us how he found the story and tapped into the minds of executives to help readers understand Southwest's unique yet successful environment.
How did you decide to do the Southwest Airlines piece?
I'd met Gary Kelly a few times and thought he was in an interesting position: following (with one guy in between) the colorful Herb Kelleher, Southwest's founder, he seemed a little drab, but next to the CEOs at other airlines he seemed quite colorful. When I saw the Edna Turnblad pics, I knew I needed to do a story on him. One of those cases where the art helped get me off my duff and do what I should have done much earlier.
How did you get access to the top executives? How did you get them to share details with you?
I called the company and asked for time with him and others. As I said, I'd visited there on prior stories. I'd like to think it has something to do with me personally, but the sad (and wonderful) truth is that working for a huge and important paper like The New York Times means that doors open quite quickly in most cases.
On getting them to share, I find that if I'm reasonably well-informed about the subject and then ask some honestly-curious questions, people are great about opening up and talking. I try to have fun and laugh and often the interview subjects do the same. Plus, this is a company that cultivates its image of being a little whacky, so it wasn't exactly a hard sell.
What techniques did you use to get in-depth details about how this company operates and feels?
I read up before visiting and did some phone interviews to make sure the trip would be a success. Then went to Dallas and saw as many people as I could and asked away, without worry that they wouldn't want to answer questions. So, the CEO's assistant was kind enough to cough up the stuff about getting his big high heels online and the other in-drag stuff, and others shared, too. I'd say this was a pretty straightforward reporting task. No tricks involved.
What was the biggest challenge you faced when reporting this story?
The story was about Southwest's corporate culture, and how it affects the airline's business. Challenge was to keep it focused on the culture, which is a soft topic not quantifiable, and deal only very briefly with more concrete stuff that has numbers and hard facts to back it up. As business reporters, we're drawn to those numbers and hard facts, as we should be, but this was one story that set out to dwell in mushier areas. So maybe the bigger challenge here was in the writing -- what to leave out.
What tips do you have for other business writers when profiling a company's CEO?
Make the story about the person and not just a look at the company through his or her eyes. If there is something really interesting about the CEO, narrow the piece to that and be willing to exclude all the usual corporate doings that can lard up a story. The more we report, the more sprawling out stories tend to become, and that's a disservice to readers. Most stories should really be about one thing. So, truly make it a profile of a person.