🎩 Hats Off (And On, And Off Again): The Ridiculous Art of Tech Leadership

Let’s get one thing straight:
Tech leadership is not a job.
It’s a chaotic costume change where you rotate through 14 different hats a day—half of which you didn’t ask for, and a few of which are actually on fire.
Welcome to leadership.
Here’s your wardrobe.
🧢 The “Visionary” Hat
(a.k.a. Making up the plan as you go and praying nobody notices)
You’re supposed to steer the ship.
You’re also supposed to know where it’s going.
Only nobody gave you a map, and the compass is running on a dead Jira ticket from 2021.
So you paint a bold vision.
You inspire. You talk about roadmaps like you didn’t just finish Googling “what is a roadmap.”
You fake it like a champ—and guess what?
That’s leadership, baby.
🎩 The Executive Translator Hat
(fluent in C-suite and developer passive-aggression)
One minute, you’re decoding some VP’s buzzword soup ("synergize our agile growth enablement matrix"), and the next, you’re explaining to your dev team why no, we actually can’t rewrite the entire codebase in Rust just because we’re sad.
You're not bilingual.
You’re poly-corporate.
đź‘’ The Therapist Hat
("It’s not you, it’s tech.")
At least once a week, someone breaks down in your (virtual) office.
Impostor syndrome, burnout, micromanagers, weird Slack energy—whatever it is, you’re the unofficial shrink.
Do you have a psych degree?
No.
Do you listen like one?
Also no.
But you do hand out validation, empathy, and the occasional “screw that, you’re awesome” like it’s part of your benefits package.
🪖 The Human Shield Hat
(Protect the team. Always. Especially from that person.)
If someone’s asking your team for a “quick MVP by Friday,” your job is to step in like a digital bodyguard and whisper,
“That’s not how any of this works.”
You absorb pressure so your people can breathe.
You take the heat. You reroute the nonsense.
You defend like a paladin with admin access.
đź§™ The Technical Advisor Hat
(You haven’t coded in months, but Stack Overflow still haunts your dreams)
You’re supposed to stay “technical”—but also be in 17 meetings a day.
You still care about clean code and architecture, but these days your pull requests are mostly comments like:
“This looks great. What does it do?”
You're not out of touch.
You're just managing more than just the stack now.
(But yeah, maybe skim a few GitHub repos before the next retro.)
đź‘‘ The Culture Curator Hat
(Spoiler: Culture is not free pizza and Zoom trivia)
It’s on you to build the kind of culture that doesn’t suck.
One where people aren’t afraid to speak up. One where feedback is honest.
One where someone says, “I love this team,” and means it.
That’s on you.
And no, HR won’t fix it.
They’re busy making a Canva graphic for Mental Health Awareness Month. You?
You’re creating an actual healthy environment, one 1:1 at a time.
🧢 The “Why Am I Still in This Meeting?” Hat
(Time-tracking this for therapy later)
Some hats are just… punishment.
🎬 Final Hat: The Anti-Hero Hat
You’re not here to be a “boss.”
You’re here to lead. To protect. To challenge the crap that wastes time and kills talent.
You’re here to rip up the old leadership playbook and write a better one—with sarcasm, substance, and a little rage-fueled optimism.
So yeah, tech leadership means wearing a lot of hats.
But wear them your way.
And when one no longer fits? Burn it. Build your own.
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