Learnings from a Manager's Past: Part 1 - Diving In

Learnings from a Manager's Past: Part 1 - Diving In Context Look, I'm not managing people anymore. That chapter of my life closed around early 2022. It was only a five-year stint, but man, those years were packed with lessons. I wanted to jot down some of the stuff I learned, the experiences and learnings, just to have it somewhere. I'll try to keep it in order... as best as I remember. Before the Real Deal I've been coding since 2008-2009. Got promoted to Senior Software Engineer quickly, then to Lead Software Engineer by 2011. The new title sounded fancy, but it was mostly just me keeping tabs on one other person, technically speaking. Planning features, writing stories, tracking progress—stuff I was already doing for my own projects. So, I don't really count that as "management." For me, it only started when I got my first proper direct report. The First Step: Into the Deep End When: Q4 2017 People Managed: One There I was, happy as a clam, thinking I'd just keep coding away, when my boss drops this on me: "How about you take over the Engineering Manager role?" Or whatever the title was, some "Lead of Technical Squad" thing. I was like, "Wait, what?" So, I ask about the responsibilities, and he kinda... glossed over it. Said it was basically what I was doing, plus one direct report. Looking back, he played it smart. If he'd laid it all out, I probably would've said no thanks. I was all about the individual contributor and hard skills life. Anyway, they'd already hired someone for my "team," which meant I missed the opportunity to interview the guy. Big rookie mistake. As any manager knows nowadays, hiring the right people is half the battle. One clear memory I got from this position is this one time, we're hashing out the design for an abandoned-cart feature. My direct says, "You need to listen to my ideas." It threw me for a loop. I was used to just talking code. But he was right, he needed to feel heard. I listened, even though I knew his approach wouldn't work. Thing is, he felt dismissed. Learning: "You gotta listen, really listen, weigh things up, and explain your reasoning. To your team, to anyone." That was a wake-up call. I started reading up on management, realizing how many good engineers get stuck with bad managers. It's a real problem. And being a manager? It's way more than just telling people what to do. It's managing work, careers, expectations, your own sanity, office politics, how you talk... the whole enchilada. Around then, I got to do some interviews, hire someone myself. That was cool. Finding someone who clicked with me and my direct? That felt like a win.

Mar 30, 2025 - 18:51

Learnings from a Manager's Past: Part 1 - Diving In

Context

Look, I'm not managing people anymore. That chapter of my life closed around early 2022. It was only a five-year stint, but man, those years were packed with lessons. I wanted to jot down some of the stuff I learned, the experiences and learnings, just to have it somewhere. I'll try to keep it in order... as best as I remember.

Before the Real Deal

I've been coding since 2008-2009. Got promoted to Senior Software Engineer quickly, then to Lead Software Engineer by 2011. The new title sounded fancy, but it was mostly just me keeping tabs on one other person, technically speaking. Planning features, writing stories, tracking progress—stuff I was already doing for my own projects. So, I don't really count that as "management." For me, it only started when I got my first proper direct report.

The First Step: Into the Deep End

When: Q4 2017
People Managed: One

There I was, happy as a clam, thinking I'd just keep coding away, when my boss drops this on me: "How about you take over the Engineering Manager role?" Or whatever the title was, some "Lead of Technical Squad" thing. I was like, "Wait, what?"

So, I ask about the responsibilities, and he kinda... glossed over it. Said it was basically what I was doing, plus one direct report. Looking back, he played it smart. If he'd laid it all out, I probably would've said no thanks. I was all about the individual contributor and hard skills life.

Anyway, they'd already hired someone for my "team," which meant I missed the opportunity to interview the guy. Big rookie mistake. As any manager knows nowadays, hiring the right people is half the battle.

One clear memory I got from this position is this one time, we're hashing out the design for an abandoned-cart feature. My direct says, "You need to listen to my ideas." It threw me for a loop. I was used to just talking code. But he was right, he needed to feel heard. I listened, even though I knew his approach wouldn't work. Thing is, he felt dismissed.

Learning: "You gotta listen, really listen, weigh things up, and explain your reasoning. To your team, to anyone."

That was a wake-up call. I started reading up on management, realizing how many good engineers get stuck with bad managers. It's a real problem. And being a manager? It's way more than just telling people what to do. It's managing work, careers, expectations, your own sanity, office politics, how you talk... the whole enchilada.

Around then, I got to do some interviews, hire someone myself. That was cool. Finding someone who clicked with me and my direct? That felt like a win.