I was doing this talk, which I’d done dozens of times before. Good, well-practiced deck. I was speaking to CTO-types (current and aspirational) as a favor to a friend. This was a monthly morning coffee chat for this crew, and they invited folks like me to speak. It was on a weekday morning near Slack in downtown San Francisco.

No problem.

Practiced talk, small group, low stakes. I was editing the title slide to update the location and name of the event. No practice necessary; again, I’d done it before.

The piece was based on this piece called Stables and Volatiles. The brief pitch. Stables are those who happily work with direction and appreciate that there appears to be a plan and the calm predictability of a well-defined schedule. Volatiles are the opposite. Read the piece; I like it.

Finished quickly. I was told this was more about a discussion than a presentation. Fine with me. Q&A tells me precisely how well the deck landed, and I’d done this talk enough to believe the Q&A would be rich. Healthy banter. It started that way. Questions about my first stint at Apple and whether well-known people were Stables or Volatiles, but then Leo in the Back Row lost his shit.

“This is bullshit. It’s a false dichotomy.” Leo, the CTO in the Back Row, was pissed about my presentation. For those without ChatGPT at the ready, a false dichotomy is “the fallacy of presenting only two choices, outcomes, or sides to an argument as the only possibilities, when more are available.”

After some back and forth, I told Leo, the CTO in the Back Row, that, like most of my writing, I liked to describe humans in stark, clever ways. This often took the form of a “THIS or THAT” black-and-white structure, but I was 100% clear that the answer to humans was a hard-to-define grey area. My job was to get you to think, not to define every possible configuration of human behavior.

I’d delivered that answer before, and it worked, but Leo, the CTO in the Back Row, was having none of it. He was still angry and — now, I am guessing — because I’d wasted his time. He was promised a structured model, and I delivered confusing poetry.

Leo, the CTO in the Back Row, was the Police. And the Police don’t like poetry.

Guess What, Leo

I have another false dichotomy for you: the Poets and Police.

Poets:

• Finish things. Usually.
• Use rich language to describe abstract situations.
• Believe well-formed, highly descriptive ideas make the world an understandable place.
• Are fine with ambiguity because they understand it’s all just shades of grey.
• Fall in love with ideas. They’ll fall in love with a single choice word.
• Like to use the word “feel” because feelings are distilled intuition expressing themselves as inspiration.
• Love thoughtful compliments.

Police:

• Finish things. Wow, they finish things.
• Crave well-defined structure and rules.
• Believe rules make the world an understandable and measurable place.
• Hate ambiguity because it provides no direction.
• Deeply enjoy both debating and enforcing those rules. They believe this is how you make future measurable progress.
• Will debate a single word that is out of place until clarity is achieved. (Poets do this, too.)
• Are excellent at measuring anything with metrics. Are unlikely to believe unmeasurable truth.
• Never use the word “feel” because feelings are irrelevant to getting the job done.
• Appreciated well-defined accomplishment.

Two things.

First, as a Poet, I know I am describing the Police from my perspective. Police will profoundly disagree with many of the attributes I describe. I am eagerly listening.

Second, yes, this article is similar to my much earlier piece on Organics and Mechanics, but I feel it’s stronger writing.

Third, I am making up a third thing. To annoy the Police who were keeping count because that is how we Poets roll.

Success is Both

As a self-declared Poet, I can confidently describe the Police because it is a job requirement that develops strong working relationships with these essential humans. I need them because the Police do the challenging work of keeping the trains on time. This isn’t simply holding conductors to a schedule but also maintaining the trains, taking care of the track, and ensuring we have a qualified staff of humans to do all this work. Oh, and how about a budget? How are we going to afford all of this? Someone needs to build a credible business plan for this train company so we can afford to keep the trains on time.

As a self-declared Poet, we also need to understand the aspirational goals of this train company. I also understand the importance of consistently sharing this vision with everyone. I know we need to listen because we need to understand how the company feels. I’m adept at organizing teams of humans with differing ideas and skills. It’s an endless puzzle that I enjoy attempting to solve. I love celebrating our victories. I feel our failures deeply, but I know that with the Police, we will learn from these failures.

Listen. Leo. The CTO. You there — in the back row. I get why you’re mad. See, while we differ in how we view the work, we are the same regarding what’s essential. We want the team to succeed, and we want them to advance. I’ve learned some of my favorite moves watching you work, Leo. I’ll work hard to try not to waste your time with too much poetry if you work hard to understand that poetry is part of how we describe and achieve the impossible.