An in-flight interview with Southwest's leadership and an on-time arrival
While flying as far southwest as Southwest flies
Hello readers, friends, and those who fill the middle of the Venn diagram.
I launched this Substack without a specific plan, but I wanted a place to share a bit of the behind-the-scenes of my full-time reporting and photography work. Twitter was a great platform for journalists and outlets to promote work they were proud of and share context and analysis behind interesting reports, but its rapidly deteriorating utility has me wondering if a longer-form approach here on Substack could work instead.
I personally think that journalism as a whole could benefit from sharing and explaining more of the process with news consumers. Separately but concurrently, my job offers some singularly enjoyable and valuable reporting opportunities, and I’d like to share more from that.
I should note off the bat that I am writing this independently, not in collaboration or under review by my employer. Like Twitter has been, this is my personal platform, all thoughts are my own, retweets are not endorsements, etc.
With that out of the way…I thought this would be a good opportunity to highlight my recent feature, out this week on The Points Guy and in our aviation newsletter, on Southwest’s efforts to prevent another meltdown comparable to last winter’s, and how it plans to try and convince customers that it can be reliable — at least as much so as any other airline. The story is based on interviews with airline CEO Bob Jordan, Chief Operating Officer Andrew Watterson, and VP of sales Dave Harvey, all conducted on board a Southwest flight above the Pacific Ocean.
Read here: Southwest has a plan to get back on track after holiday meltdown. Here's what execs tell TPG
In short, after some poor communication early in the crisis, and an insistence in the ensuing weeks that this was really a weather disaster, not a Southwest-specific problem, it felt notable to hear the airline’s leaders own the mess throughout our conversations. It can be paraphrased as: “We messed up badly. Here are the specific places where we messed up, and how we’re addressing those. Here’s how we want to communicate that to customers.”
For more on that, take a look at my full report over at The Points Guy. I’m biased, but I think it’s worth reading, and if nothing else, your click and read over there will help me justify using Substack.
Now, a bit on how this interview happened.
In April, Southwest unveiled a special Hawaii-themed livery (paint job) on one of its planes. Southwest has a ton of special liveries, including a bunch of planes painted in the state flags of some of the airline’s key markets. This jetliner was a bit unique because one, Southwest launching Hawaii service was a huge deal when it happened, and it remains a key part of the airline’s business plan, and two, because it was the first state livery that didn’t incorporate the flag.
Read more about the design here: Southwest unveils stunning new Hawaii-themed aircraft
We were invited to send a reporter to an employee event on a Friday in Long Beach, one of Southwest’s departure points to Hawaii, where the plane would be “officially” unveiled at a rampside employee event.
From there, the plane would fly as a special employee charter flight to Honolulu with various airline employees on board, before making its way to each of the airline’s Hawaii bases, and finally entering service for passenger flights.
As part of the pitch, we were invited to hitch a ride on the charter flight to interview Jordan, the CEO, and any other employees on board, with no limits on topics — meaning that despite the theme of the event, we didn’t have to agree to focus solely on Hawaii, as (genuinely) fascinating as Southwest’s push there may be.
So, that was that. I flew to Los Angeles the night before the event — I managed to clear the upgrade list and get a lie-flat seat on a Delta 757, which was nice since I was incredibly tired and really needed the nap I was able to take. I stayed at a hotel by LAX, and Ubered to Long Beach the next morning.
The event itself was solid, in terms of photography and reportage. We were able to access the ramp and enjoy unobstructed views of the new plane flying by, landing, and taxiing.
There were speeches, ceremonies, and celebrations, and a few hours for lunch (which I spent wolfing down a salad and trying to edit photos, write a story, and file it before EOD in New York).
I’d estimate the flight was around half full, so even though the charter boarded like any other Southwest flight, even people in the lower boarding groups (like me) had their choice of seats.
The flight was fun, with a casual vibe and a lot of casual walking around and chatting. There were drinks passed around by the working flight attendants fairly early for toasts to the airline’s employees and founder, Herb Kelleher — the drink options included Wild Turkey, notoriously Herb’s favorite drink.
It all made for a decent interview environment, minus the engine noise on my tape recorder. Still, casual chats are a great way to learn more about any business or topic. Plus, I found out that I was sitting across from Southwest’s TikTok team, and told them that a video a few weeks earlier had made me actually laugh out loud.
The interview with Bob was a bit more of a formal sit-down thing, only because his attention was in high demand — I needed someone from the PR team to help me get on his radar for a few minutes. We did the interview sitting towards the front of the plane, far from the engines, making for the best audio quality I could hope for while I took notes as a backup.
Incidentally, it wasn’t my first in-flight interview with a Southwest CEO; in late 2021, I interviewed retiring CEO Gary Kelley on an actual commercial Southwest flight from Dallas to San Antonio.
We landed, and there was another ceremony with photos and speeches, followed by a reception with food — and more speeches — in the terminal.
After a hasty bite to eat while listening for anything newsworthy in the speeches, I picked up my rental car, drove to the hotel, and slept for about 11 hours (it had been a really long day, and a really long week). I took the next day off to recover, explore Oahu a very little bit, and enjoy “Spam Jam,” and flew home on a rough redeye the next day after a quick detour to see the memorial at Pearl Harbor.
All that was left was to write the actual story, which took a few weeks — the topic was more or less evergreen until early summer, and a mix of busy days at work, breaking news, a sick kid, and moving meant I kept having to put it at the bottom of my triaged to-do list. But I finally had time to finish it, and got it up well within its relevancy window.
If you’ve made it this far: thank you for reading!
This is probably longer than my usual posts here will be, but I’m looking forward to using Substack to try and highlight some of my work and shed some light on what I do, how I do it, and why I might make certain choices. And maybe more, as time goes on.
Till next time!
And in case you missed it: