The Worst Customer Experience EVER

(and what I learned from it)

Sep 25, 2025

Happy Rosh Hashanah to those who celebrate!

We talk a lot about strategy. Segmentation, channels, flows, discounts, CX, etc. But sometimes the best lessons come from the most basic place: being a customer.

I’ve said this before, but the reason I’m great at leading CX teams is that I’m a difficult customer. I absolutely hate it when things go sideways and no one steps up to fix them.

Over the past few weeks, I’ve had three very real, very memorable customer experiences. One was infuriating. Two were fantastic. All three taught me something simple and true that every brand, regardless of size, can learn from.

But most importantly, they reminded me how critical it is to understand the “job to be done” and who your customer really is.

Let’s get into it.

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HELLO, IS ANYBODY HOME??

I was with T-Mobile for years. It worked. I never really thought about it, which is exactly what you want from a phone plan.

But then my wife finished medical school, and we discovered something cursed and beautiful: the physician discount.

There’s a whole underground world of discounts for doctors. Cell service, hotels, rental cars. If you’ve got an MD or DO after your name, you can apparently save $9 a month on almost anything. So naturally, we went shopping.

AT&T had a solid offer. A new customer deal, some decent trade-in value so I could trade in the iPhone 14 for a free 17 Pro, and the sacred physician discount. We made the switch. That’s when the fun began.

The number port didn’t go through. I gave it a day, nothing. Called support, sat on hold and got tossed around for over 5 hours (!) on a Sunday. Finally got someone who told me the port had been canceled by mistake and they could not reset it for 72 hours. No explanation. I’d have to wait a few more days to try again.

Meanwhile, I was stuck in no-man’s land. Couldn’t receive texts. Couldn’t verify anything. Couldn’t even log in to some of my accounts.

I spent the better part of a week bouncing between T-Mobile and AT&T, trying to find someone, anyone, who could fix it. Every call started with the usual security questions that I can now answer in my sleep, and ended with a transfer to someone who had even less context than the person before.

Nobody followed up. Nobody emailed. Nobody said, “I’ll see this through.” It was just one long game of customer support hot potato.

Eventually, I filed a complaint with the Better Business Bureau. That’s what finally worked. Someone from the Office of the President reached out. The tone shifted immediately. They fixed everything in under 24 hours. Port completed. Pricing fixed. All good.

Which is great, but also kind of insane? I had to escalate to a government-adjacent complaint system just to get someone to take the wheel.

The takeaway:

The problem wasn’t the port. It was the absence of ownership. There were plenty of people involved, but not one of them thought, “This is mine to solve.”

And that’s where it all unraveled.

It didn’t matter how many systems they had in place, or how polite the reps were, or how many teams I got passed between. If one person had actually stayed with it, this wouldn’t have spiraled into a weeklong mess and a BBB complaint.

If you lead CX, this is the thing to focus on. Not faster macros or better routing logic. Just make sure someone actually stays on the case and feels OWNERSHIP.

IT SHOULDN’T BE THIS EASY

A few weeks ago, my son decided to go full WWE and launched himself off the couch onto our dining table. The table didn’t stand a chance. It snapped clean in half. He was fine. The table was done.

We needed a new one. I texted a friend who works at Nathan James, asked for a recommendation, and ordered the one she suggested. It arrived fast, looked great, and everything was going smoothly, until one of the chair screws didn’t fit properly.

Normally, this is the part where you get stuck. Support asks for your order number, then five photos, then a video, then tells you to try a different screw. You go back and forth for a few days, and maybe, eventually, they mail you a single part in a padded envelope with no tracking.

Instead, Nathan James made it stupidly easy. I got a prompt to submit a short video through their support tool, Hark. I recorded it on my phone, hit send, and figured I’d wait to be disappointed.

Twelve hours later, on a weekend, someone followed up asking for the lot code on the chair, and said they had already processed a full replacement chair.

It felt oddly professional. Like this was a company that had already decided to believe its customers unless they had a reason not to. They removed every ounce of potential friction. I have not smiled this way about a customer interaction in a hot minute.

The takeaway:

Nothing about this interaction was showy. No apology note or gift card. No overdone brand moment.

What made it memorable was the lack of friction. I didn’t have to chase anyone. I didn’t have to prove anything. The process worked, and it worked fast, and that was more than enough.

Most people don’t want to be wowed. They want to be done. And if you can give them that, if your team can make the boring stuff seamless, you’ll get a lot more loyalty than any surprise and delight stunt can buy.

This one stuck with me. Mostly because I expected to have to fight for something basic, and I didn’t.

GET OUT OF THE WAY

My wife wears Figs. She’s a doctor, which means she’s either in scrubs, changing into scrubs, or ordering more scrubs. We placed an order during one of their recent drops, and one of the items didn’t fit. So we went to reorder. That’s when I noticed the discount code from the original purchase wasn’t applying to the second one.

Technically, it made sense. It was a one-time code, and this was technically a second order. But practically, it was just an exchange. I sent a quick note to support explaining what happened, fully expecting a few rounds of back-and-forth or at least a conversation about policy.

Instead, twenty minutes later, I got a reply from someone who had already refunded the difference. They didn’t ask for screenshots. They didn’t explain why this was an exception. They didn’t quote the terms and conditions. They read the note, understood what was going on, and just fixed it.

And that was the whole thing.

The takeaway:

Figs clearly knows who their customer is. These are busy professionals who don’t have the time or the energy to chase down a promo code. They’re not looking to negotiate. They’re just trying to reorder something that didn’t fit.

There was nothing flashy about this interaction, but it stuck with me because of how little friction there was. It didn’t feel like support. It felt like a brand that respected my time and understood the context before I even had to explain it twice.

The refund was already processed. The response was clear and final. There was no follow-up needed. That’s what good support looks like. Not fast for the sake of fast, and not generous for the sake of PR, just functional in a way that feels rare.

Support should never make the customer carry the weight of the mistake, even if the system thinks it’s “working as intended.” The best teams know when to step aside and let the fix happen.

Figs did. And I’ll remember that the next time we’re reordering.