Customer Service: A Meaningful Lesson in What NOT to Do

Soooo here's the last chapter in "Why Customer Service Still Sucks (and how it could be so damn easy)."

I have a $200+ travel credit with Southwest. I got it from a trip we had to cancel and keep forgetting to use. Over the weekend, I went to book a new flight for an upcoming trip. When I attempted to add the travel credit, it wouldn't allow it.

Their system would not allow me to book with the credit because the credit will expire between the booking date and the travel date. Ok, fine - I get they have to set and follow a set of policies.

Here is where the whole scenario gets absolutely ridiculous...

I call customer service to see if there is anything they could do. I've been flying Southwest forever - Companion Pass, Top-Level Status, Business Card, the whole shebang. There was a time I was basically on a first-name basis with their flight attendants.

Anyway...The agent who answered the phone was very nice. However, she was absolutely no help what-so-ever.

Here is their policy🙄:

I cannot use the credit now unless I complete the travel before February 24th. However, If I call anytime on or after February 25th, they can extend the credit and give me an additional 90 days (from the call) to use the credit. I can literally request this 90 extension of the credit anytime over the next year.

Soooo in other words:

I have a credit with Southwest. I want to use that credit. They will allow me to extend and use it beyond the expiration date, but only AFTER it is expired. My brain hurts from trying to understand their logic in establishing these policies.

This is straight up policy spelunking. It's people chasing edge cases instead of solving problems. It's like telling someone, "Sure, you can have that thing you've already paid for, but later...and maybe."

This got me thinking. 🤔 This isn't an airline problem. This is a business problem.

It's important to note: The thing that separates companies that people LOVE from companies people TOLERATE is not price. It's not loyalty programs. It's not how fancy your app looks or behaves.

It is how you handle the moment someone actually needs help!

Read that again.

This is a reality that hits really close to home for me. We are in the real estate business - a totally different industry, but the same rule applies:

Here's how it looks in our world:

Someone is about to move their family...or drain a savings account...or carry two mortgages for a month...or explain to their kids why they are changing schools...or leave the community they've nurtured for 20 years...or or or...

These are not low-stakes transactions. Therefore, when emotions are already running hot, the worst possible move is to respond with something that sounds like a shrug wrapped in professionalism.

Clients don't need to hear all the reasons something cannot be done. They need a partner who is willing to pick up the phone, make the call, escalate the thing, think creatively, try one more angle, and get shit done.

Half the job is knowing the rules and how the system works. The other half is knowing when to push on them and how to ethically (and legally) circumvent the system.

Clients remember who fought for them, who anticipated every issue, who said, "Hang on - let me see what I can do." They remember who had their back when it would've been easier to shrug and blame the process.

That's the job. THAT is customer service - not hiding behind processes and defending broken systems, but rather solving the human problem sitting in front of you.

The reality is, there isn't a single "villain" here. Nobody woke up one morning and said, "Let's frustrate customers today!" This happens because policies get rigid...because systems are built to protect the company, rather than to serve their customers...because frontline employees have zero autonomy.

The problem with companies like Southwest Airlines is they fail to realize one very important business truth. Customer service is not a cost center. It is your reputation in motion.

In my experience, Southwest's brand looked like, "Sorry. Call back later."

This post is already long, so I'm not going to get into all the ways they could/should have handled this situation differently.

Tell me about your worst "this makes NO sense" customer service experience.

If we can collect enough stories, maybe we can start a support group...or write a "how to (or how NOT to)" guide.