A Story about How Southwest Airlines Lost a Customer

Steven Duran
5 min readJul 7, 2016

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I always fly Southwest Airlines if I can help it. In my experience, they’ve got the best prices, and they fly to almost anywhere I could ever want to go. My love for Southwest goes beyond the cheap flights or the convenient destinations. When I fly Southwest airlines, I just feel different. Whether it’s the flight attendants or the customer service reps, I am always treated with respect and nearly always with a smile as well. The smiles are extra meaningful to me these days because now I usually fly with my almost 2 year old daughter. Let’s be honest, almost NO one smiles when they see a baby get onto a long flight.

I remember one time I was flying cross-country on this Boeing 737, and the flight attendants started cracking jokes throughout the entire safety instruction process. The guy on the mic was equal parts witty and self-deprecating which made for a really enjoyable experience in a normally boring safety routine. Turns out that my experience of the fun safety instructions presentation on that flight wasn’t unique. In fact, it’s something that frequently takes place on Southwest flights all across the country. However, it turns out that over the years not everyone appreciates the humor as much as I do. One customer took extreme measures to inform Southwest of her disapproval. This story comes from Alexander Kjerulf and I thoroughly enjoyed every line:

One woman who frequently flew on Southwest, was constantly disappointed with every aspect of the company’s operation. In fact, she became known as the “Pen Pal” because after every flight she wrote in with a complaint.

She didn’t like the fact that the company didn’t assign seats; she didn’t like the absence of a first-class section; she didn’t like not having a meal in flight; she didn’t like Southwest’s boarding procedure; she didn’t like the flight attendants’ sporty uniforms and the casual atmosphere.

Her last letter, reciting a litany of complaints, momentarily stumped Southwest’s customer relations people. They bumped it up to Herb’s [Kelleher, CEO of Southwest] desk, with a note: ‘This one’s yours.’

In sixty seconds, Kelleher wrote back and said, ‘Dear Mrs. Crabapple, We will miss you. Love, Herb.’”

I used to think that I couldn’t love Southwest Airlines any more than I already did until I read this story. In fact, I think I’m one raucous night away from getting a Southwest tattoo. I think there’s a number of things that we can learn from this story, but I only want to focus on three key pieces of business insight:

1). The CEO went to bat for his people — I’m an ESTJ on the Myers-Briggs scale which means that I naturally gravitate toward people who show a strong sense of loyalty. Herb Kelleher clearly understood loyalty and put this money (technically lack of money) when his mouth (technically a letter) is before he eventually retired as CEO. To me, this is the exact kind of leadership example that inspires people which sets the tone for an entire organization. Bravo Herb!

2). This company understands who they are — The most important (and unsexy) thing you can strive for in business is organizational health. The thing about organizational health is that it starts with a deeply rooted sense of identity. Once a company or brand understands who they are and how they act, then all decisions should flow from that place. When Herb (I’m gunna pretend like we’re on a first name basis) sent Mrs. Crabapple that response, he wasn’t just handling a disgruntled employee, he was making a first stance about who Southwest Airlines is and how it will be successful. Clearly it worked because Southwest is doing just fine for themselves.

3). The Customer Service team sent a customer complaint to the CEO — One of the biggest signs of a good business leader is someone who can be approached by anyone in their organization. The fact that the customer service team at Southwest Airlines felt comfortable enough to send the CEO of a $2.2B organization a letter from a disgruntled customer is truly remarkable. The fact that the CEO of a $2.2B airline took the time to read the letter and respond to it is even more incredible. I’m in the middle of building a new start-up organization so this notion of leaders being made available to their employees at every level really strikes close to home especially when managing a team of millennials.

Whenever a business makes a claim that customer service is important to them, there are several criteria that I think we should consider. First, the way in which an organization treats its employees is certainly an indication of how it will inevitable treat it’s customers. Second, when the executive leadership at an organization is involved in the nitty-gritty of customer satisfaction, that’s when you can tell that there’s something special going on there. Have I ever had a bad experience with Southwest airlines? You bet I have. Why do I continue to almost exclusively fly Southwest? Because loyalty is a two way street. You don’t give up on someone or a company for a single mistake, especially if they’ve earned your trust or admiration. The reason that I trust Southwest Airlines and know that they give a damn about their customers is because they didn’t give a damn for Mrs. Crabapple and her inability to enter into the business culture that Southwest has built and fostered over the last forty years.

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Steven Duran

Director of eCommerce | BigCommerce | Shopify | Direct-To-Consumer | B2B | Amazon