executive vs product-thinker

Topic: A personal year-end reckoning with a difficult year
Axis varied: voice
A: Executive B: Product Thinker

What to notice

A frames the year as bets that did not pay. Effort staked, outcomes bet on.

B frames it as a problem mis-specified. “The problem I was solving last year was not the one I named at the start. That gap is where most of the year went.”

The tell: A’s unit of analysis is the decision; B’s is the problem definition. B is still trying to get the question right; A has moved on to accounting for the answer.

A: executive

The year delivered two significant failures, and I am not going to describe them as growth opportunities. A project I had staked twelve months of effort on closed without the outcome I had bet on. A relationship that had been genuinely important to me changed in ways I did not choose. I am writing this to account for both clearly, not to resolve them into a more comfortable story.

The project failure was in significant part mine. I had seen signals of drift early and chosen to hold position rather than adapt. That decision was explicit. I owned it in the room and I defended it when it was questioned. It was wrong. Looking back, I was optimizing for the outcome I wanted rather than the one the situation was actually offering, and I held that position well past the point where the evidence supported it.

The relationship is harder to account for. Marcus and I built something that mattered, and then we did not. What I know is that we communicated well when things were stable and poorly when the stakes were highest. The gap between what I said and what I meant grew until it cost us more to close than we could agree to pay. I do not have a clean read on how much of that was circumstances and how much was accumulated failure on both sides. I am not pretending to.

What I am choosing to carry forward: a shorter timeline for naming a problem before it compounds, and a genuine skepticism of positions I find myself defending primarily because I invested in them. The next question I am actually sitting with is what I am prioritizing now - not as recovery, but as a real recalibration of what I am willing to bet on.

I do not know yet whether I am getting that right. That is the honest signal.

B: product-thinker

The problem I was solving last year was not the one I named at the start. That gap is where most of the year went.

The project - call it Meridian - was supposed to help a small team of independent researchers coordinate their work without drowning in a ticket tracker nobody updated and a chat tool that buried decisions under reaction emojis. The job to be done was clear: “I want to know what’s happening without attending every meeting.” We had alignment on the problem. What I got wrong was the user.

I had built for the researcher I interviewed three years ago, not the one who existed now. The friction I was solving had shifted, and I had not gone back to check my assumptions. When the pilot ended without adoption, I wanted to explain it as a resourcing problem, a timing problem. The post-mortem I avoided until months later was plainer: I had shipped a solution to a problem the current user no longer had.

That reckoning coincided with a harder one. A friendship with someone I had worked alongside for seven years changed in ways neither of us chose well. What I want to say is that I handled it gracefully. What is true is that I framed every conversation as a product problem - here is the friction, here is the fix - when the job she was trying to do was not to resolve a process gap but to feel heard without a solution following right behind.

Both failures share a shape. I led with what before I understood why. I had answers before I confirmed the question.

What I am choosing to carry forward is not a lesson about resilience. It is a question I have started asking at the beginning rather than after the fact: whose problem is this, and am I still talking to the right version of the person who has it?