The Unbossing of America

How We Hollowed Out Management and Left Workers Adrift

May 01, 2025

When my daughter entered the tech world a decade ago, she carried a fierce creative spirit — and a belief that great leadership would help her grow.

Instead, she encountered chaos: well over a dozen managers in 10 years — some good, some forgettable, some damaging.

" I felt like I was always starting over — having to prove myself in new teams, under new leadership, with new goals."

Her experience isn’t unique. It’s a warning signal.

Watching her navigate the churn — and hearing her honest reflections — forced me to think deeply about how far we’ve drifted from the kind of leadership that once defined the best companies. This isn’t just a generational shift. It’s a collapse of something essential.

This is a story about what we’ve lost — and how we might begin to find it again.

The Era When Management Mattered

My formative years in business came during a very different era—one when becoming a "manager" wasn't just a title; it was a milestone you had to earn. For anyone serious about their career, management was a critical stepping stone. It demanded more than ambition. It required training, self-awareness, and a true commitment to leading people.

Back then, management wasn’t handed out—it was earned. You were expected to grow into the responsibility. Front-line managers would often stay in their roles for several years before being considered for promotion or a move elsewhere.

Formal training was common. Informal mentorship was essential. If you were lucky, you learned from great managers. If not, you still learned—by watching those who clearly didn’t have a clue.

Years later, that gap became starkly clear when my daughter was promoted to manager. She asked me a question that took me by surprise: “How do I know how to be a good manager?”

My first thought was—how the hell is it possible she doesn’t know the answer to that? Then I asked her, "Have you ever had a great manager?"

She paused. "One," she said.

"Well then," I told her, "make a list of everything that manager did that inspired you—and another list of everything the bad ones did that drove you crazy. Assume you'll do the opposite. Combine the two, and you'll have a great start."

That moment made me realize how little guidance young people get these days—not just on how to manage, but even on how to want to manage.

One of my own early breakthroughs came under a CEO who saw potential in me—but also recognized my flaws. He encouraged me to work with a corporate psychologist who helped me uncover my blind spots and begin leading with greater intention. It wasn’t easy, but it was transformative. I wasn’t perfect, but I was growing into the craft of leadership.

The Google Experiment: Scaling Without Hierarchy

Years later, I joined Google. While the company was legendary for its talent, it was also defined by an internal tug-of-war.

The founders valued brilliance, flatness, and the power of the individual contributor. The CEO, Eric Schmidt, knew that to scale, the company needed real management.

"The founders wanted to avoid becoming a traditional company. Eric knew the company couldn’t scale without structure."

Their compromise created a flat, functionally driven org that rewarded engineers and discouraged layers. Managers were required to oversee at least seven people—the so-called "Rule of 7."

Product Managers were tasked with leading cross-functional teams without direct line authority. Their performance wasn’t judged by how many reported to them, but by how many wanted to work with them.

"Leadership at Google wasn’t about control—it was about influence. That’s a powerful model, but also turns out to be an incomplete one."

This all seemed like a great compromise and worked extremely well in the early years—fostering the formation of a lot of intrapreneurial teams and tons of innovation.

But, as I learned later, it wasn’t necessarily the best organizational design for something growing as rapidly as YouTube.(Substack Post to Follow).

What Got Lost Along the Way

While this structure encouraged collaboration and flattened power hierarchies, it also left gaps in how management was practiced.

Managers weren’t responsible for hiring their direct reports. Everyone at Google was hired through a generic process focused on your functional role—not the actual team you’d be joining.

The company also put only modest emphasis on mentoring or developing junior talent, teaching people how to give feedback, run 1:1s, or manage performance.

The company had a very systematic performance management system including OKRs (Objectives and Key Results) and quarterly reviews, but the critical softer side issues were not the focus—it was all bits and bytes—and popularity.

When companies like Google grew rapidly, they needed to retain top talent. The easiest way to do that was to offer managerial titles, even to those untrained or uninterested in managing. Management systems like the Rule of 7 quietly eroded.

Promotions didn’t come with the tools or structure to help new managers succeed—let alone the people assigned to them as their direct reports.

The Rise of Shallow Leadership

The pattern I observed at Google was repeated across most of the biggest tech players. As more untrained managers entered the tech ecosystem, new patterns emerged:

Company-hopping became far more prevalent.
Team-hopping became common.
Disconnection grew.
Mentorship faded.
Communication became ephemeral.

A new kind of leadership crisis took hold—one defined by motion without depth and the impersonalization of the personal.

What Ambitious Young Talent Hoped For — And What They Got

When my daughter entered the tech world, she — like so many — carried with her the hope that creativity and strategy could coexist. That work could be a place where thoughtful leadership, mentorship, and real growth were possible.

"Creativity has always been a driving force for me — but what drew me to product design was realizing that creativity and strategy could be partners, not opposites."

But instead of finding scaffolding, she found churn.

"Constant reorgs don’t just disrupt projects — they stunt personal growth."
"Without mentorship, managing up became survival."

In her last gig, besides reporting to 6 different bosses in 5 years, she literally worked with 15 different product managers. Imagine that!

To grow in that world, she had to become her own advocate, her own coach, and her own culture leader.

"Culture leadership isn’t optional. If you want better teams, you have to build them."
"Promotions and titles follow impact — not noise."

We didn’t just lose good management. We asked a whole generation to succeed despite the structures that should have been helping them.

The Slackification of Leadership

Remote work and digital tools were supposed to make work more flexible. And in many ways, they did. But they also made leadership more impersonal and disconnected.

Zoom check-ins, Slack messages, texting, Google Doc comments, even email—these replaced office hours, mentorship chats, and the quiet confidence that comes from real-time connection.

"Slack is not a substitute for stewardship. Zoom can’t replace mentorship."

Without real human connection, feedback became shallow. Misunderstandings multiplied. Trust atrophied.

Once I left Google and began doing CEO and executive team coaching, I saw this pattern repeated time and time again.

The singular insight? Sometimes leadership is just showing up. Having coffee. Walking down the hall. Solving problems face-to-face.

It seemed so damn simple and natural. But it clearly wasn’t anymore.

The Work-From-Home Amplifier

I’m not against hybrid work. Experts suggest that hybrid models, when implemented thoughtfully, support productivity, well-being, and talent retention. But when companies go fully remote without investing in culture or connection, everything fractures.

Managers don’t meet their people. Teams rarely gather. Mentorship happens, if at all, by chance.

My daughter’s recent experience—she had one boss she NEVER met in person. Not once. No attempt to get to know her, no investment in her growth. Just a name on Slack, a square on Zoom.

In remote-first organizations, young employees are especially at risk of becoming uncoached, unseen, and unsupported.

That disconnection is not sustainable.

Meta Made Things Worse — And Silicon Valley Followed

In early 2023, Mark Zuckerberg declared Meta’s "Year of Efficiency," laying off more than 10,000 employees and restructuring management layers. Middle management was slashed.

"We’re going to be more proactive about cutting projects that aren’t performing... and lean into efficiency across the board." — Mark Zuckerberg

Other tech giants quickly followed — Google, Amazon, Salesforce, Stripe, Shopify — copying the model as if it were new gospel.

The results? Some short-term wins, but deeper fractures too:

Spans of control ballooned.
Burnout surged.
New hires floundered.
Trust eroded. Culture fractured.

The culture didn’t just shift. It fractured.

“Meta didn’t just restructure a company. It helped redefine what ‘management’ means across an entire industry—at least for now.”

A Frontline Perspective: What Young Leaders See Now

Through all of this, my daughter came away with a hard-won understanding of what it takes to survive — and grow — in today’s fractured environment.

Here’s how she now defines the difference between a good manager and a bad one:

"A good manager creates clarity, trust, and space for growth. They set clear expectations, advocate for their team's work, and foster an environment where feedback is a tool for growth rather than fear. They recognize the unique strengths of individuals and invest the time to understand how to unlock their potential. A good manager leads with transparency — sharing the 'why' behind decisions — and invites their team into the problem-solving process. They know when to coach, when to challenge, and when to step aside and let someone lead."

By contrast:

"A bad manager often creates confusion, mistrust, and a sense of stagnation. Signals of bad management include inconsistent or unclear communication, lack of follow-through, micromanagement, or the inability to advocate for their team. In environments led by bad managers, fear often replaces trust — people feel hesitant to share concerns or take risks. Growth conversations rarely happen, or when they do, they feel performative rather than genuinely supportive."

And ultimately, she summed it up this way:

"The strongest signal of a good manager is this: when you're working with them, you feel a little braver, a little smarter, and a little more capable than you did before. And over time, you see it reflected not only in your own growth, but in the collective strength of the team they lead."

These aren’t just reflections. They’re the essential markers of what real leadership should still look like — and too often doesn’t.

Will AI Make This Better—or Worse?

The rise of AI in the workplace is already reshaping how we work. But will it help solve the management crisis—or deepen it?

On one hand, AI can be a powerful tool:

It can automate repetitive managerial tasks—like scheduling, status tracking, and documentation.
It can surface performance signals, suggest training paths, and even summarize 1:1s.
It can free up managers to focus more on people than process.

But here’s the risk: If we treat AI as a substitute for leadership rather than a support for it, we may make the problem exponentially worse.

As organizations rush to adopt AI to boost efficiency, the temptation will grow to flatten orgs even more, reduce human layers, and let machines take over “management.” But AI cannot mentor. It cannot coach. It cannot replace the human presence that makes people feel seen, valued, and invested in.

Without a deliberate course correction, AI may supercharge the unbossing trend—delivering even more scale, but even less soul.

As futurist John Naisbitt predicted in Megatrends: “The more high tech we become, the more high touch we need.” He saw this coming as far back as the 1980’s.

We’ve built high-tech workplaces. Now we need to restore the human touch that once defined great management.

The Silent Exit of Mid-Level Talent

While younger employees like my daughter feel the erosion of leadership firsthand, mid-level managers — the traditional glue of organizations — are quietly walking away.

A Korn Ferry survey found that 44% have experienced management cutbacks, and 40% now feel directionless. Gallup found that only 44% had received formal management training.

"Middle managers are being asked to do more with less — often without the tools, authority, or time to lead effectively."

This is the true organizational hollowing: not just a thinning of roles, but a loss of stewardship at the center.

The Path Forward

This is our inflection point. We can use this moment to go back to first principles—and actually build something better than what came before. AI can more than deliver the theoretical savings companies hoped to achieve through unbossing. In fact, it creates space for the return of true leadership:

Treat management as a position to aspire to—not overhead to minimize. Make it a destination, not a detour.
Re-establish a structured development path to becoming a manager. Training and apprenticeship should be prerequisites.
Return to principles like the 'Rule of 7.' Keep spans of control human and scalable.
Reaffirm the value of in-person interaction. Encourage travel, team off-sites, 1:1’s, and in-the-room leadership presence.
Encourage longer tenure in managerial roles. Build in rewards for staying and growing with your team.
Create transparent, well-rounded performance reviews. Incorporate feedback from direct reports, peers, and leaders.
Invest in ongoing manager training. Teach mentorship, coaching, emotional intelligence—and make it a cultural cornerstone.

Some companies are already showing what this looks like. IDEO, for example, has long prioritized leadership development as a core part of its culture. Managers are trained to foster creativity, provide consistent mentorship, and lead with empathy—hallmarks of their design-driven philosophy. It's not an accident that IDEO’s teams are known for high trust and high output.

Firms like Atlassian and HubSpot have also restructured performance management to include peer feedback, mentorship programs, and longer-term leadership incentives. IBM and Blackstone are investing in structured management apprenticeships and internal leadership pipelines to strengthen continuity and coaching across teams.

These organizations are seeing stronger retention, deeper engagement, and better results—not despite more management—but because of better management.

“The companies that win in the AI age will be the ones that pair smart tools with smarter leadership.”

Epilogue: What We’re Really Losing

The deeper story here isn’t just about org charts or efficiency. It’s about meaning—and what we’ve quietly lost in the race to optimize.

Once upon a time, I flew across the globe to meet every person I managed. At the head office, I held “breakfast with the boss” (at 8:00am!), which was always full. That would seem absurd today. But it built something: trust, alignment, connection.

Today, that kind of presence is seen as a luxury. And soon—with AI and automation accelerating—what little remains of it may vanish.

Speed without context
Performance without cohesion
Output without culture

“We may soon have organizations that run smoothly on paper—but feel lifeless in practice.”

Employees will drift—unmoored, unmentored, and uninspired. And companies will wonder why.

Because tools don’t build culture. Dashboards don’t coach. And no tech stack can replace a manager who knows you, sees you, and wants you to grow.

It’s not too late to put people back at the center of leadership—where they’ve always belonged.