Listening is one of the more critical diagnostic skills you can practice.

At one company I worked with, the support team kept getting tickets for their fax modem banks… busy signals, dropped connections, intermittent failures across the document ingestion system. The issue could last for hours if not longer at times.

And every time it happened, the team would review the hardware. They would check the intake software that controlled the modems, restarting the software controllers. They would pull logs and look for errors. Even testing equipment by running extensive self-checks. They usually found nothing wrong.

Then the problem would go away on its own, and apparently this had been going on for months.

One day it happened while I was in the room. I listened to the troubleshooting for a few minutes and asked one question:

“Has anyone called the number to hear what it’s doing?”

Blank looks.

I picked up a phone and dialed the line. Fast busy tone. Beep beep beep.

“The problem isn’t here. It’s at the exchange. Call the telco.”

An hour later the carrier opened a service investigation and found intermittent hardware failures on their end.

Months of tickets. Hours of internal troubleshooting per incident, and the final fix was simply getting it to the right people. Granted one of the guys asked me later how I knew what that kind of beep meant. I referenced past work at an ISP (oh, the skills you pick up over a career).

The instinct when something breaks is to look inward. Check your code, check your hardware, check your config. But sometimes the problem isn’t in your domain at all. And no amount of expertise applied to the wrong layer will get you there.

The diagnostic that matters most is often the simplest one nobody thought to run.

Today I walked through an empty warehouse, powered down the internet connection, collected the last IT equipment for recycling, turned off the lights, and locked the door.

For almost six years, I was often the one to handle the difficult conversations, the one to stop and drop everything to run halfway across the state to handle an emergency because we needed boots on the ground. Terminations, restructuring staff, the meetings nobody wants to be in, a fraction of my work but just as critical as anything else. That just became my job while building out an enterprise grade IT environment for the company (IT that just worked and stayed out of the way). The kind of work that never ends up in a job description, but the kind of work that finds the person willing to do it.

After a few years it became a running joke. If I showed up to a job site unexpected, the first question was “who’s getting let go now?” followed by “Bryan’s going to be the last one here. And if Bryan’s gone, we’re all done anyway.” Polite chuckles. It was always in good fun. I never took it personal and teased them right back.

Every single person I was tasked to let go from the company I tried to do so with as much dignity, respect and empathy as I could provide regardless of the reasons for the termination. Even in rough cases I still reached out and offered my hand in parting.

My time with this company is now past tense. And I was, in fact, the last one out the door. No handshake. No hug. No “you did your best.

If you’ve ever been the person in your org who does the work nobody else wants to do, you already know how this story ends. You don’t get a ceremony. You get an empty building and a set of keys to return.

And you look for the next chance to do the right thing where you can.

#OpenToWork. #Leadership

As technology leaders, our most critical job is understanding the actual architecture of the tools we buy. If we evaluate probabilistic AI models using the same procurement mindset we use for enterprise software, we expose our organizations to catastrophic, invisible risks. I looked at the recent DoD/Anthropic negotiations as a case study in how dangerous this category error can be.

(Read, The Room Where It Gets Built — Essay #8: LLMs Are Not Shelf-Stable Products)
 

You walk into a store. The price tag makes no sense. “Who’s paying for this?!?”

Not you. The store did the math. They figured out they don’t need you. They don’t need ten of you. They need one of a different customer who pays sticker and doesn’t blink.

I wrote an essay about how this same dynamic is playing out across the entire hardware market and most people haven’t noticed. About what happens when data center equipment comes off cycle in three to five years. And about why even a flood of cheap enterprise surplus might not help you, because the consumer operating system is being redesigned to lock you out of it.

Thirty years of pattern recognition on this one.

(Read, The Room Where It Gets Built — Essay #6: You Are a Decimal Point)