We’ve created an amazing world of convenience. AI is incredible, and texting is fantastic—smart inventions that have improved our lives in many ways. But when the flawless surface cracks, how do we find our way back? And in the inevitable mess that follows, who is the asshole? Is it me, the frustrated customer? The overworked, script-bound representative? Or is it none of us?
Are we all just slaves to the machine?
My recent experience with Verizon began with a simple, practical need. My 256GB phone was running out of storage, and my watch battery was dying by 5 or 6 PM. Both had exceeded their usefulness for me. The initial upgrade process, handled through the Verizon App and a quick call to an online sales representative, was a model of modern efficiency. I compared plans with other carriers, secured high trade-in values for my old devices, and within three days, my new phone and watch arrived. So far, so good.
The first hiccup came with the watch band. I discovered it wasn't just about width, but also about loop size. The tiny "S" on the package, hidden behind the "49mm" label, was a silent sign of a problem that the sales rep had not mentioned; whoops, a mistake was uncovered. The band was a struggle to get over my hand, a significant flaw for a device that needs to be recharged daily.
This is where the story shifts from a simple upgrade to a frustrating, hours-long ordeal.
My journey to exchange the band exposed a core flaw in our hyper-connected, text-and-bot-driven world. I began my search on the Verizon app, seeking a simple solution, and was immediately plunged into a maze. An hour later, after navigating a labyrinth of AI bots and live agents, I realized a key truth: we, as customers, have no idea what department handles what. What’s “Customer Service” at one company might be “Technical Support” at another, making it nearly impossible to pose the right prompt to get to the right place. To make AI work, we need to ask the right questions to get to the right place—but the map to that "right place" is constantly changing. The tech itself isn't the asshole here; the system’s design, which traps us both in a rigid, unforgiving process, is the villain. Human logic gives way to the system’s unyielding demands.
Here's a perfect example. I asked an AI assistant: "What department at Verizon Wireless deals with a watch band exchange?"
The AI’s answer was a masterclass in direct, clear information. It told me I'd deal with the customer service or sales department, and it laid out the timeframe, conditions, and where to go. It even provided a handy list of what information to have ready, a perfect prescription for a smooth and efficient exchange.
But the real-world experience was anything but smooth.
Days 3, 4, 5, and 6 were a blur of calls, holds, and frustrating conversations. I was promised call-backs that never came. I re-explained my simple problem to multiple agents, starting over each time because no one had a record of the previous conversation. Finally, after an hour on the phone, I was given an order number for the exchange. The victory felt hollow; this simple task had been far more difficult and time-consuming than the entire process of buying the new devices in the first place.
But the worst was yet to come. I was eventually transferred to an agent in the Sales Department who insisted there was no way to exchange just the band. His script-driven solution was for me to return the watch and the band, which would trigger a "new order." This, he explained, would require me to pay the sales tax on the new devices upfront. When I questioned this, I was told with an air of finality, "Mr. Robert, that's why we have terms and conditions. It's all in the terms and conditions."
In person, nobody has ever called me “Mr. Robert” before.
Even worse, the new "order" would inexplicably raise my monthly bill. I had wasted so many hours, and now the solution was not only convoluted but also more expensive. My face flushed with frustration. The agent insisted that a supervisor would tell me the same thing: I should just "read the terms and conditions." The representative wasn't the asshole here; he was a slave to the system, forced to follow a script that didn't allow for an ounce of creative thought.
Finally, after insisting, I was transferred to a supervisor named Jacob. Jacob, I have to admit, was a skilled listener. After a brief but honest back-and-forth, he bypassed the entire broken system. He recognized the absurdity of the situation and the value of a single, simple decision. The watch band was worth $199. He credited my account for $220 to cover the band and the sales tax. "No need to send the band back," he said. The mission was accomplished, and I went to the Apple Store online to buy a new, correctly sized band. An extra workaround step, but successful nonetheless.
This experience brought to mind what customer service used to be.
You'd go to a store, talk to a human, show them the product, and leave with a "yes" or "no" based on store policy, sometimes relying on a human judgment call. The good retailers who understood this—stores like Nordstrom, known for accepting almost anything back—made you want to shop there. Today, companies like Costco and Amazon stand out because they simplify returns. REI Co-op goes even further with a one-year satisfaction guarantee on most products. I find it especially helpful for shoes.
The Verizon snafu is not exclusive to me. It's a symptom of a larger issue.
We have a society that prioritizes the speed and efficiency of technology, yet we still struggle to address human needs when things go wrong. We're all stuck in these digital mazes, trying to find someone who can go beyond a script and provide a creative solution. This is the ultimate paradox of our era: the very tools meant to simplify our lives have often created a system that can be pretty frustrating. There's plenty of room for improvement and opportunities to make AI and our interactions with companies much smoother. If we apply the same problem-solving mindset to our technology and business processes, we could all benefit greatly. I believe others have ideas on how to fix this, and I'd love to hear them.
Meanwhile, suppose you’d like to learn how not to be an asshole. In that case, my new memoir is available Tuesday, August 19th, in audiobook format through Audible, Spotify, Apple Books, and other popular audio services, or you can request it in CD format at your local library. Check it out.