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Crumpled Paper: "The Case for Becoming a Manager"

Published on Sunday, March 29, 2026 by Alexander Mason

Author note: This blog post style is trying something new. Instead of trying to write long-winded about a subject I’ve researched, I wanted to give a real-time reaction to something I just have read.

These micro-blogs will be much less formal and may contain social / political commentary. The goal is for these to serve as an online bookmark for things I find interesting and my opinion on them.

I always check-in with myself and ask if going into management was the right decision for me. We all have our own reasons for chasing the career ladder. On one hand, I want to climb to the highest rung. And on the other, I don’t want to limit my abilities and shift away from the high-impact technical work that I do.

I thought engineering management would sate me. Turns out it has just made me hungrier. I am always looking for the mental pivot that is needed for that next level.

The most valuable thing management has taught me is how to communicate with precision when someone else’s work depends on it. When you’re an IC, unclear communication slows you down. When you’re a manager, unclear communication breaks your team. That difference in consequences makes you learn faster than you would any other way.

I’ll give you a specific example. A few months into the role, I was briefing a team member on a content project. I had the whole thing mapped out in my head: the structure, the angle, the audience it needed to reach. I started writing it all down, basically handing over a blueprint. And then I caught myself. I was about to do the thing I’d always done as an IC, solve the problem my way, except now I was asking someone else to execute my solution instead of finding their own.

So I pulled back. I shared the goal instead. Here’s who the piece is for, here’s what it needs to accomplish, here’s why it matters right now. And what came back was different from what I would have built. It was better in places I hadn’t considered, because the writer brought their own perspective to a problem I’d only described the shape of.

Interesting note, I think I have room for growth here. I need to get better at articulating the problem for all stakeholder involved. CEO, IC, PM, doesn’t matter. They all deserve clear cut requirements and goals.

“Build a program with no dependencies that can beat Stockfish level 17.” Straightforward. The model worked for 30 minutes and came back with something that won consistently. But when he looked at what it actually built, the agent had downloaded Stockfish and used it to play against itself. Task completed. Goal completely missed.

Once he reframed the prompt to specify intent (”build your own chess engine from scratch, the goal is to evaluate whether you can implement an engine that competes”), the model understood. The difference wasn’t complexity. It was clarity about what success actually meant.

That self-correction loop is a management skill. Noticing when the output is wrong and asking what you could have communicated differently, instead of just blaming the execution.

The better you are at articulating intent and separating the goal from the implementation path, the better those [agents] perform.

Now seem’s like a good time to go update my five-year plan.

Source Article:

https://newsletter.thelongcommit.com/p/the-case-for-becoming-a-manager

-Alex

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