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The Great Management Unbundling
How AI Can Bridge the Growing Manager-Employee Gap
Tim Monzures
September 23, 2025
Your Boss Doesn't Have Time for You (And It's Not Their Fault)
Remember when your manager actually knew you? Not just your work, not just your name, but your actual situation—whether you were struggling with that Python script, gunning for that senior role, or just needing someone to notice you were languishing?
Yeah, those days are gone.
The numbers are staggering: managers today oversee roughly triple the people they did a decade ago1 . We've gone from one manager for every five employees in 2017 to one for every fifteen in 2023. And it's accelerating.
I spent a decade at Apple managing teams, growing from a solo act to twelve direct reports before I finally promoted my first manager underneath me. Even with Apple's resources and my genuine love for the role, twelve people pushed the absolute limits of what I could handle while still being, you know, an actual human being to each of them.
So when I read about managers now handling 20, 30, even 36 direct reports, the word I think of isn’t efficiency. I think of chaos. I think about Eryk Jeznach, the Vancouver manager who told the WSJ he wakes up at 4:30am in "a consistent state of inadequacy.”
That's not a management problem. That's a math problem.
And here's the kicker: companies think they're winning.
Number of white-collar employees at U.S. public companies, change since the end of 2021: WSJ
The Great Gutting: Silicon Valley's Latest Obsession
Google just cut 35% of its managers. Intel nuked half its management layers. Estée Lauder and Match Group? Twenty percent, gone.
Josh Isner, president of Axon (the body camera folks), called their old structure of four employees per manager "borderline offensive." While four employees for a manager may be on the light side, what’s offensive is not knowing the details of your team.
The religion of "flat organizations" has officially reached fever pitch. Boards and investors see fewer managers as a sign of strength, not weakness. It's the corporate equivalent of intermittent fasting—painful, trendy, and supposedly good for you in ways that nobody can quite explain. The financial savings sound great, sure. But at what human cost?
Here's what's actually happening on the ground:
One Microsoft manager now juggles eight direct reports and openly admits he doesn't know if his team members are married or single. "There is a boundary, and I do not cross it," he says. Professional? Sure. But also kind of dystopian.
Another manager with 36 reports (!) has essentially given up on management altogether. His strategy? "Ask each other for help before coming to me." That's not delegation; that's abdication.
The companies pushing this aren't struggling startups trying to stretch their runway. They're profitable giants who've decided that middle management is fat to be trimmed rather than the connective tissue that holds organizations together. They're betting that in a world of Slack, Notion, and endless productivity tools, we don't need those human bridges anymore.
They're half right. And completely wrong.
Let me paint you a picture of what's actually happening in these supersized teams. Because the real damage isn't visible in the org chart—it's in the thousand tiny fractures that appear when human connection gets stretched too thin.
Managers drive 70% of the variance in team engagement.2 Seventy percent! That's not a correlation; that's a sledgehammer of causation. And that manager juggling 20 direct reports? Good luck being on the right side of that variance.
The Communication Death Spiral
Teams working in separate locations experience lower levels of trust and higher levels of conflict3 . Now imagine those same dynamics when your team members can't even get five minutes with their manager.
Last June, I wrote about how communication overhead increased significantly as my Apple team grew past 25 engineers4 . But at least we had communication. These new mega-teams? They're running on fumes and Slack threads.
One manager told the Journal he keeps sticky notes divided by sub-team because he literally can't keep track otherwise. The next billion dollar AI company? AI sticky notes.
The Engagement Cliff
When's the last time someone with 20 reports gave meaningful weekly feedback to everyone? They're lucky if they remember everyone's project, let alone their development goals.
The result? A growing disconnect between what employees need and what managers can physically deliver. When roles aren't clear, teams struggle with frustration and misalignment5 . And with managers stretched this thin, nobody's clarifying anything.
The Silent Epidemic: Career Development on Life Support
Remember mentorship? That quaint idea where your manager actually helped you grow? It's become a luxury good.
Employees are learning to "manage up" in the worst way possible—not by taking initiative, but by becoming walking status reports. They have minutes, not meetings. They pitch their accomplishments like they're on Shark Tank because they know their manager won't notice otherwise.
The system now rewards self-promotion over actual performance. The loudest voices win, not the best ideas.
The Uncomfortable Truth About "Self-Starters"
Let's address the elephant in the supersized room: this new world works great for exactly one type of person.
You know them. The self-promoters who treat every Slack message like a press release. The ones who never needed mentorship because they were born knowing how to manage up. The "Michael Jordans" that Axon's president name-dropped—the ones who supposedly "don't need the same level of attention."
Cool. What about everyone else?
What about the brilliant engineer who's too introverted to fight for airtime? The junior employee who doesn't even know what they don't know? The high performer going through a rough patch who needs someone to notice before they burn out?
They're getting left behind. And companies know it.
Here's what nobody wants to admit: we're creating a two-tier system. The loud, the confident, the already-capable—they'll thrive in this brave new world of radical autonomy. Everyone else gets to figure it out or flame out.
That's not leadership. It's organizational Darwinism dressed up as "efficiency."
Enter AI: The Janitor, Not the Manager
Alright, enough doom and gloom. Let's talk solutions. Because while companies are busy cosplaying as flat organizations, technology is quietly building the scaffolding that might actually make this mess work.
By 2030, AI could automate up to three hours per day of routine activities6 . Three hours. That's not replacing managers—it's giving them back the time to actually manage.
But let's be real about what's happening right now, not in some magical AI future.
What AI Actually Does Today (The Unglamorous Truth)
Forget the hype about AI replacing jobs. Here’s what it’s really doing: the grunt work that made managers want to quit in the first place.
That Bayer VP with 24 reports? Routine expense approvals are auto-handled.
Microsoft managers use Copilot to generate meeting summaries so they’re not rewriting the week every Friday.
Tools like Asana and Motion auto-schedule work and flag obvious conflicts so calendar Tetris isn’t a full-time job.
This isn’t revolutionary. It’s janitorial—and that’s fine. Floors should be clean.
Where it gets interesting is the force-multiplier effect: some tools watch patterns and flag risks earlier, or track workload to pre-empt burnout. Useful, yes. But notice what’s missing: these tools mostly move data around. They don’t maintain shared context or protect commitments across channels. They summarize what happened; they rarely detect what’s about to not happen.
The AI landscape today, in four buckets:
Admin automation: expenses, approvals, calendar math.
Summarizers & searchers: notes, digests, retrieval.
Task routers & schedulers: assignment, prioritization, workload.
Signal pingers: reminders and check-ins.
Valuable—yet mostly reactive. They tidy. They don’t coordinate.
The Hinge
The gap is obvious once you feel it every day: today’s AI sweeps the floor but doesn’t hold the room together. It moves information; it doesn’t maintain shared understanding. It files the receipts; it doesn’t notice the promise we made in last Tuesday’s standup is already off-track. That missing layer—the part that keeps teams coordinated and people seen—is exactly what I couldn’t find. And it’s what finally pushed me to leave Apple.
This Time, It's Personal
I loved managing my team at Apple. Twenty-five engineers, three countries, new hardware every year. It was controlled chaos, and when it clicked, it was magic.
But the job slowly morphed into archaeology—digging through email, Slack, calendar shards, and meeting minutes to reconstruct decisions, owners, and why we did what we did. Meanwhile, the work that actually mattered—coaching, spotting risk early, protecting people from avoidable fire drills—got whatever scraps of time I had left.
I didn’t leave because I disliked management. I left because I loved it enough to fix what was breaking it.
Attrove: handles the archaeology so managers can do the anthropology.
Cross-channel context: Email, Slack, meetings, and calendar stitched into a single, living narrative of who-decided-what-and-why.
Commitment capture: Promises made in meetings or threads are automatically tracked, with owners and dates—no more “who had the ball?”
Early-risk detection: Emerging bottlenecks and dependencies are flagged before they become escalations.
Human-first design: Free managers from status archaeology so they can coach, decide, and build culture.
One early user told me Attrove gave them back two hours a day. They didn’t spend it writing better updates. They spent it having real conversations.
That’s the point.
The Pendulum Will Swing (But Not How You Think)
Here's my prediction: in two years, some McKinsey report will breathlessly announce that companies need more managers. The pendulum always swings back. But it won't swing all the way.
We're not going back to the cozy days of four-person teams and weekly one-on-ones for everyone. That ship has sailed, been decommissioned, and turned into a WeWork.
What we're heading toward—what we need to head toward—is something different. Managers with bigger teams but better tools. AI handling the administrative overhead so humans can focus on being human. Intentional design instead of just cutting layers and hoping for the best.
The companies that win won't be the ones with the flattest org charts. They'll be the ones who figure out how to scale human connection alongside team size. Who use technology to amplify management rather than replace it. Who remembers that even Michael Jordan had Phil Jackson7 .
The Choice We're Making
Every company slashing management layers is making a bet: that efficiency trumps effectiveness, that tools can replace relationships, that people will figure it out because they have to.
Some will. Most won't.
We can do better than organizational Darwinism. We can build systems that help overwhelmed managers actually manage. We can create tools that surface what matters instead of drowning everyone in noise. We can recognize that in a world where work is more complex and distributed than ever, we need more connection, not less.
The management crisis isn't a problem to be solved with layoffs or reorgs. It's an opportunity to reimagine how we support each other in doing the best work of our lives.
Your boss will always be busy. But this time around, they’ll have the bandwidth to know not just your name, but you as a person.
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