Southwest Airlines

Herb Kelleher, the legendary co-founder and former CEO of Southwest Airlines, was known for his humour and unique leadership style. Here is an interesting anecdote that shows his personality.

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 she wrote a complaint after every flight. She didn’t like that the company didn’t assign seats, the absence of a first-class section, not having a meal on the flight, Southwest’s boarding procedure, the flight attendants’ sporty uniforms, nor the casual atmosphere.

Her last letter caught Southwest’s Customer Service employees off guard with yet another long list of complaints. They had always responded swiftly and nicely to her, but she kept complaining. This was a never-ending story, and thus, they forwarded it to Kelleher’s desk with a short note: ‘This one’s yours.’ In sixty seconds, Kelleher wrote back: ‘Dear Mrs. Crabapple, We will miss you. Love, Herb.’

Nice versus kind

A nice CEO might have had the customer service team send a polite apology or even a voucher to smooth things over. An angry CEO would have become defensive and may not even have responded. But Kelleher did something different. He didn’t bend over backwards to appease her. He didn’t tell her what she wanted to hear. He didn’t become insulting. He responded honestly yet gently.

Kelleher wasn’t just nice—he was kind, and there is a big difference. Being nice is about smoothing things over. Being kind is about doing the right thing, even when it feels uncomfortable. In business and life, kindness—especially when tied to integrity and purpose—will always take you further.

The differences (and the overlap)

While kind and nice are certainly related, they are far from the same, and it is important we understand the distinction: