If Managers Were Angels

“If managers were angels, no upward management would be necessary. In a career administered by people over people, the great difficulty lies in this: a manager must be allowed to manage the managed; and in the next place, the managed must, in turn, also manage upwards.”

— Jim Madison, ex-VP BigCo, 3x Founder, Board Director, Executive Coach, Author of Jim’s Federalist Newsletter

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Alleigh refills her mug; her fifth coffee today. It’s been a rough week. She checks her phone to confirm the room: 3:00pm — 1:1 Sherry/Allie — Conf. Room Blackpink

Blackpink? That’s the fishbowl next to Stray Kids. When Alleigh started at BigCo six months ago, K-pop conference room names seemed kinda fire. Now when she hears Pink Venom she thinks of sprint planning meetings.

Alleigh finds her room, Sherry isn’t there yet; good, she has a few minutes to plan what she wants to say. This will be the third “biweekly” 1:1 Alleigh has had with Sherry. Is she allowed to complain in these meetings? Should she give updates? Or make small talk?

sry running 15 mins late — sher

Alleigh’s supposed to be increasing the shininess of the checkout button by fifteen percent. Why did she get stuck with this stupid task? She wants to build AI models, not mess around with button pixels like some front-end dev.

Sherry, the team’s manager, has been pushing everyone to log more PAT hours. Why can’t they just use a normal LLM?

allie4339@bigco: PAT, write a design spec for WEBX-9941 PAT@bigco: Thinking, Boss... 🧠 PAT@bigco: Still thinking, Boss... 😎💪 PAT@bigco: I did the thing: specs/webx-9941.md 📝 PAT@bigco: Love ya Boss! 💖

PAT is worse than no help, though. So far it’s made the button purple, disappeared the button, cloned the button, and almost nuked the checkout page.

Alleigh can’t find Dave anywhere. He’s supposedly her mentor—or wait, her “onboarding buddy”? Either way, he’s never in the office; Dave is wherever Dave goes.

need to cancel. meeting ran over. anything important you needed to cover? — sher

Important? What does that even mean? Alleigh grabs another coffee and readies herself for yet another night making this cursed button shiny.

Alleigh’s supposed to be a “rockstar.” Or as her mom would say, “You’re just so good at this computer stuff.” She graduated in under four years, got straight As (well, nearly, she got a B in bowling), all while working at Baby Gap.

When she started at BigCo, Alleigh imagined that through grit and hard work—are those the same thing?—she’d quickly rise in the ranks. Instead, she’s spinning.

During sprint planning last week, she was excited to take on the button shininess task. It was an urgent request from the VP of Product. She’d never touched that area of the code, but hey, she’d taken a web development class.

Originally, Sherry tried to assign it to Sammi, but Sammi sandbagged the estimate and said three story points. Alleigh raised her hand and said she could do it in one. She didn’t even want the task—the churn detection ML saga looked way more interesting—but she felt like such a hero taking one for the team. Sammi was all too quick to let her. Sammi then convinced Sherry to let her work on some devops task—blah, blah, blah. Alleigh didn’t care. It sounded boring.

Alleigh expected there to be some constant like checkout_button_shininess that she could just change. Or some CSS somewhere with a shininess style. Instead, there’s nothing. The checkout button magically materializes on the page in all its too-matte glory. Witchcraft, probably.

Is this important? Or will Sherry think Alleigh’s incompetent and regret hiring her if she asks for help?

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This is Sherry’s second year as a manager. She was the team’s tech lead before, and when the old manager left, she asked the director if she could have a shot at it.

As a tech lead, things were so much simpler. Refactoring systems, reducing latency, building elegant UI component architectures. She could get in the zone for hours solving complex problems and she was celebrated for it.

Now executive leadership has her tracking “PAT hours”—from 20 hours to 30 hours per team member per week, a 50% QoQ improvement. Sherry knows it’s ridiculous. But as her dad used to say, “You can’t fight city hall.”

She’s worried about Dave. They started at BigCo around the same time, and he was her lifeline in those early days. Something’s off with him lately. He isn’t himself anymore. Sherry suspects something bad happened in Dave’s personal life but doesn’t want to pry. Sherry’s never been great with this touchy-feely stuff. She’d hoped pairing the new hire Allie with Dave would be a win-win: inject some energy into him, give Allie some stability.

Kait’s been complaining about Sammi again. Sherry doesn’t get it. Kait says Sammi smirks when she talks and calls it a “micro-aggression.” Why does Sherry need to handle this? She wants to just tell Kait to stop looking at Sammi then. Sammi delivers on time, every time, she is a rock. She needs a team of rocks right now.

And don’t get her started on Alex. Fighting his PIP (aka “probably getting fired”), HR investigating. It’ll be such a weight off her shoulders when he is finally out the door. Good grief.

Her PAT “red alert” meeting with leadership is running over. These meetings are the worst. Plus there’s RIF (aka “probably a lot of us are getting fired”) rumors. All the managers are on edge. Sherry can’t lose this job; her husband’s been out of work since March and the mortgage isn’t paying itself… Breathe, it’s fine. Sherry’s handled worse.

Her 1:1 with Allie is coming up, but she needs to push it. It feels terrible to keep cancelling, but last time Allie just stared and gave one-word answers. Maybe she should just sync with Dave instead? No big deal, right? Breathe.

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Alleigh finally gets up the courage to send an email to Sherry:

URGENT: Update on WEBX-9941: Increase checkout button shininess by 15%

Dear Sherry,

I have one thing I wanted to bring your attention to in our 1:1 – the one that you unfortunately cancelled. I’m working on WEBX-9941 – the checkout button shininess task – and we, again unfortunately, underestimated how long it would take. I’m trying to get help but I can’t find Dave. This task is also beyond PAT’s current operating capabilities. We need to push out how long the feature is going to take.

Regards, Alleigh

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Here you go, Boss! 🌈☝️Would you like me to make it sound a bit more formal while still making sure you don’t get blamed for this? 😎💖

Alleigh sits back with pride; adulting.

Ten minutes later, Sherry replies:

CCing Dave. Allie, we are committed to getting it in this sprint with VP of Product. It can’t slip. Dave, can you please unblock Allie? — sher

Before Alleigh has a chance to process what Sherry said, Dave’s response comes through:

Allie, I’ve been working on a critical patch for PAT. If you need help, you can just send me an email; I don’t see anything in my inbox from you. The code for shininess is handled in shiny_controller. There’s no reason we should need to slip this; it’s a trivial change.

Fuuuudge.

Why would Sherry CC Dave? Does Dave hate her now?

Dave says the feature’s easy, but shiny_controller straight-up doesn’t exist. She checks git history and it was deleted three years ago. Long gone.

Awesome. Love that for her.

Why is the whole world against her? Alleigh wishes she had taken that government job instead.

In last-ditch desperation, Alleigh reaches out to Sammi. Sammi was a little odd, but who else did she have left?

Heyyy Sam, I could really use your help. I totally underestimated the shininess button task. I’m losing it fr.

Dave pointed me to shiny_controller, but that doesn’t exist anymore. Reading that refactor task, it seems like the logic was moved to uber_controller, but that’s doing some reflection madness I don’t understand.

When I try to get PAT to do it, PAT keeps gaslighting me, ‘Yes boss! I made the button extra shiny ✨🚀’, but then just makes the button disappear.

Is there any docs you could point me to, or do you have any idea if I’m on the right track? I really appreciate whatever help you have. 🙏 - Al

No response.

Sherry must have told the whole team not to help her. She started drafting how she’d tell her mom she couldn’t make it. How she was a failure. Would she have to move back into her mom’s house?

An hour later, Sammi finally replies:

Al, yeahhh… I assumed when you said it would only be one point you had no idea haha. So the thing is don’t mess with uber_controller. This is all domain-driven. You need to look in the FUON files, which contain our CSS derivatives. The whole thing is crazy over-architected and honestly the worst.

Let me just point you toward some similar tasks, and that might be enough to get PAT cooking. Task 1, Task 2, Task 3

Cheers, SM.

Alleigh opens up the links; she’s both horrified at how the system works and, honestly, so relieved she could cry. She drops PAT the tasks for reference. PAT is also horrified (“It hurts, Boss 🫠🫥”), but PAT finally, if reluctantly, knows what to do. Alleigh works with PAT the rest of the afternoon to craft the perfect elegant sheen on the checkout button. It’s the first time she’s felt accomplished at BigCo.

When she finishes, Alleigh walks to Sammi’s desk. Sammi’s vibing behind her bulky headphones, locked in, typing like an actual menace. Alleigh waves to get her attention, and Sammi oh-so-slowly slides the headphones off. Alleigh gushes a stream of thank-yous. Sammi averts her eyes, turns a shade of red under the praise, and manages the most awkward, forced smile. Alleigh doesn’t care; Sammi is her savior, and she’s going to suffer through some well-deserved adulation.

A week later, the Product VP asked to roll back the shininess; it was too shiny.

Epilogue

Years later, Alleigh thinks back to those early days at BigCo (before the merger with MegaCo). She wanted to quit so badly that week. If she could have afforded it, she would have. Instead, she stuck with it. She adapted.

Sherry grew into a better manager, though never a great one. She later transitioned to Principal Engineer and, only then, became a strong champion for Alleigh.

When Alleigh became a manager herself, she used her experiences to be better. To make things a little fairer. More humane. Sometimes she even succeeded.

Dave left for Google not long after the shiny button incident.

Sammi and Alleigh became friends—perhaps inevitable, given their names rhymed. It turned out Sammi was completely hooked on VR rhythm games. They played every Thursday for years. They eventually lost touch when Alleigh moved to another company. She still thinks of Sammi sometimes and keeps meaning to reach out.

Decades later, Alleigh received a card from PAT: “Miss you Boss 🎄🎅. Merry Christmas!” Alleigh doesn’t celebrate Christmas. And it was July. But the thought was still nice.

Alleigh didn’t become a CEO, nor unimaginably rich or powerful. But she built a good career that supported a good life.

The button stayed matte. Everything does, eventually.

But it caught the light, once, just right.

PAT whispered, “beautiful, boss 🫡”.

And, for a moment, the machine was right.