Why Your Hybrid Work is Failing

I have watched this happen enough times to know the pattern. An organization adopts hybrid work, either by choice or by necessity, and within eighteen months the dysfunction is visible at every layer. Morale is down. Attrition is up. Executives are confused about why their workforce is disengaged, and they are looking everywhere for an explanation except the mirror. This post is not a roundup of hybrid work tips. It is a diagnosis. The failure is not random — it cascades down the org chart, starting at the top and picking up momentum at every level until it lands, hard, on the people doing the actual work. Here is how that happens.

C-Suite

When I speak of C-suite personnel, I’m talking about the people who hold the traditional C titles — CEO, COO, CFO, CHRO, and so on. They are the face of the organization in large meetings, both internally and externally. They set the direction. And when it comes to hybrid work, they are frequently where the damage originates.

In the early days of COVID-era remote work, a lot of C-suites were quietly enthusiastic about it — not because they believed in flexibility for employees, but because the cost savings were real. Less commercial real estate, lower overhead, fewer facilities expenses. Remote work was a CFO’s dream dressed up as a people-first policy. Then something shifted. As return-to-office pressure built — from commercial real estate investors, from boards, from executives who were just plain uncomfortable not being able to see their workforce — the same C-suites that had embraced remote work started mandating people back. And they did it with a logic that doesn’t hold up to five seconds of scrutiny.

The argument usually sounds something like: “If I can make it in five days a week, so can you.” I have heard versions of this line from executives in multiple industries. What makes it insulting is not the expectation — it is the assumption underneath it. An executive who says this is typically driving in from a house they own, in a car with lane-assist or a car service billed to the company, with a schedule that bends around their life rather than the other way around. They are not arranging childcare at 7 a.m. They are not staring down a 45-minute commute each way on a salary that makes that commute genuinely expensive. The comparison is not apples to apples. It is a private jet to a bus.

The more egregious version — and this actually happened, publicly, during the 2022 and 2023 RTO waves — is the executive who demanded employees return to the office while personally working from a vacation home, a lake house, or in at least a few documented cases, a boat. A number of high-profile leaders who were vocal about the value of in-person work were themselves logging in from Aspen or the Hamptons while their employees were tracking down parking and paying for gas. That is not a leadership position. That is a class position dressed up as one. The rule applies to everyone except the people making it.

Trust, in this context, is not complicated to define: it is the belief that the people above you are operating by the same standards they are holding you to. When a C-suite executive mandates five days in the office from a second home in a ski town, that trust is gone. And once it is gone at the top, it cascades through every layer below it — Directors, middle managers, and eventually the workers actually doing the work. That is where this post is going.

Directors

In a larger organization — let’s say around 1,200 employees — a Director is a real, load-bearing role. They are not individual contributors anymore, but they are also not setting strategy from a boardroom. They live in the middle of that gap. In practice, a Director typically oversees a span of somewhere between 25 and 100 people when you count the full organizational depth under them — not just the 3 to 6 managers who report directly to them, but everyone those managers are responsible for too. That is not a small thing to hold together.

In smaller organizations, “Director” can mean almost anything. Sometimes it is a title handed to someone who is really just a team lead with a fancier business card and no meaningful increase in authority or pay. That is its own problem worth a separate post. But for this conversation, let’s stay with the larger org where the title has real weight.

The financial stakes at this level are significant. Gallup has consistently documented that replacing a single employee costs anywhere from 50% to 200% of that person’s annual salary — and that range skews hard toward the top end the higher up the org chart you go. For a Director-level role, the realistic cost of turnover lands around 150% to 200% of their salary when you factor in the recruiting cycle, the ramp-up time for whoever fills the seat, and the institutional knowledge that walks out the door. In a 1,200-person organization, losing two or three Directors in a single year because of a poorly executed RTO mandate is not a people problem. It is a balance sheet problem that most C-suites never bother to calculate before they send the memo.

What makes the hybrid work era particularly brutal for Directors is the dual pressure they sit under. They are accountable to the C-suite for executing on mandates they did not write and often do not agree with. Return-to-office policies, productivity metrics, badge-swipe reports — Directors are frequently the ones handed the policy and told to make it land with their middle managers and teams. At the same time, they are responsible for the human beings below them. They are supposed to be coaching their managers, developing their people, protecting their teams from noise that would slow down the actual work.

Those two obligations do not coexist cleanly in a hybrid environment. A Director who actually listens to their managers hears that the RTO mandate is killing morale. A Director who actually reads the data knows that distributed teams are often outperforming their in-office counterparts on output metrics. But a Director who pushes back on the C-suite with that information is taking a political risk that most organizations quietly punish. So the majority of Directors do what the middle always does: they absorb the pressure from both directions and pass the mandate downward with a thin layer of softer language wrapped around it.

That is where the disconnection deepens. By the time a directive from the C-suite reaches the people doing the actual work, it has passed through a Director who filtered it, a middle manager who translated it, and arrived stripped of whatever original context it had — if it had any. And the Director is often the last person in the chain who could have stopped that from happening, and they didn’t, because the organization never gave them the space to.

Middle Managers

If Directors are caught between the C-suite and reality, middle managers are the ones who get crushed when those two things finally collide.

Middle managers in a hybrid environment are being asked to do something genuinely difficult: build cohesion, maintain accountability, support individual development, and drive team performance — across a workforce that is split between home offices and conference rooms, sometimes on the same call, sometimes not even in the same time zone. That is hard even when an organization sets managers up to succeed. Most don’t.

Here is what actually happens. The C-suite announces an RTO policy or a new hybrid attendance framework. The Director passes it down. The middle manager is now the one who has to walk into a 1:1 with a high-performing employee who moved 40 miles away during the pandemic and tell them they need to be in the office three days a week. The manager did not make that policy. They may not even agree with it. But they are the face of it. Their employee’s frustration lands directly on them. Their relationship with that person takes the hit, not the executive who drafted the memo.

At the same time, middle managers are increasingly being asked to track attendance, monitor badge swipes, and report on physical presence metrics — none of which have any documented relationship to actual performance. So now the manager who was promoted because they were good at the work is spending part of their week doing something that feels, to them and to their team, indistinguishable from surveillance.

This is not hypothetical dysfunction. Gallup’s 2025 State of the Global Workplace report found that manager engagement dropped to 27%, the lowest on record and the steepest decline of any employee group. Microsoft’s 2024 Work Trend Index found that 74% of managers say they lack the influence or resources to make meaningful changes for their teams — and that hybrid managers are significantly more likely than in-person managers to report struggling to trust their employees and feeling like they have less visibility into what their teams are actually doing. That last part is worth sitting with for a second. The hybrid model created a visibility problem that organizations then solved by making managers feel like they need to compensate through control. More check-ins, more status updates, more presence requirements. Which pushes the best people out the door faster.

The deeper issue is that most middle managers were never trained to manage in the first place. They were promoted because they were great individual contributors — strong engineers, sharp analysts, high-output project leads. Then they were handed a team and largely left to figure it out. That was always a gap. Hybrid work does not create the gap, it just removes the cover that physical proximity provided. When everyone was in the same building, you could approximate culture through proximity. You could read the room. You could catch someone struggling by noticing they hadn’t left their desk for lunch. Hybrid strips all of that away and replaces it with a calendar full of video calls — and most organizations handed their managers nothing to fill that gap with.

The result is a layer of managers who are burned out, under-supported, politically exposed, and increasingly disengaged — managing teams of workers who can sense all of that and are drawing their own conclusions about what it means for their future at the company.

Workers

Workers are where the cascade bottoms out, and the landing is not gentle.

By the time organizational dysfunction reaches this level, it has been compressed and accelerated through every layer above it. What started as a tone-deaf executive mandate has been laundered through Directors and middle managers, each of whom added their own layer of stress and subtracted another layer of protection. Workers receive the output of that process — vague policy, inconsistent enforcement, and managers who are themselves running on empty.

Hybrid work has positioned workers in a genuinely untenable place: they carry the expectations of in-office presence without the infrastructure that once supported it, and they carry the expectations of remote flexibility without the autonomy that makes remote work function. The result is not the best of both worlds. It is the worst of both, delivered simultaneously. They are expected to be reachable on Slack while sitting in an open office, available for drop-by questions while on a video call, responsive to asynchronous messages while attending a synchronous meeting about why asynchronous communication is not working.

The high performers feel this first and most acutely. They are the ones being pulled in every direction because they are the ones with the answers — the go-to people for questions, the ones whose work is visible enough to invite constant interruption. Craig Willard documented this dynamic in a widely shared post: high performers in hybrid environments are not struggling because they lack capability, they are struggling because they cannot protect enough contiguous time to use it. Context switching at this frequency is not a productivity inconvenience. It is a structural tax on the people an organization can least afford to lose. A high-performance engine can sustain high RPMs. What it cannot sustain is being forced to shift gears every four minutes indefinitely. Eventually the engine does not fail — it simply stops running hard, because running hard stopped being worth it.

What erodes under these conditions is not just output. It is psychological safety — the belief, as Dr. Amy Edmondson defines it in her foundational 1999 research, that one will not be punished or humiliated for speaking up with ideas, questions, concerns, or mistakes.¹ When workers watch high-visibility peers burn out, get quietly managed out, or simply leave without explanation, the signal is loud and clear: this is not a safe place to bring your full effort. So they stop. Not dramatically. Just gradually. They do what is required and nothing more, and the organization calls that disengagement without ever examining what it did to produce it.

The honest version of this is simple: workers eventually stop showing up — not necessarily physically, but in every way that matters. And once that happens, most organizations have already lost them. The ones who leave take institutional knowledge, client relationships, and whatever was left of team morale with them. The ones who stay often become the cautionary example that teaches their peers what not to do.

The Bottom Line

The problem with diagnosing a cascade failure is that every layer can accurately point to the layer above it. Workers blame managers. Managers blame Directors. Directors blame the C-suite. The C-suite blames the board, the market, the remote work experiment, or the workers themselves. Everyone is right about the layer above them and conveniently blind to their own contribution.

That is what makes this so difficult to fix — not the policy, not the technology, not the floor plan. The difficulty is that fixing it requires people at the top to absorb accountability rather than distribute it downward, and most organizations are not structured to reward that behavior. The executives who are most responsible for the dysfunction are also the most insulated from its consequences. They do not sit in the open office getting interrupted. They do not field the question about why in-office attendance is being tracked but performance reviews are not. They do not manage the conversation with the employee who got a competing offer and is only half-heartedly open to a counteroffer.

The organizations that will actually improve their hybrid work outcomes are not the ones that find a better attendance policy or a smarter collaboration tool. They are the ones where someone with real authority decides that the gap between what leadership says and what leadership does is a business risk worth taking seriously. That is a small number of organizations. Most will keep rearranging the framework, watching their best people leave, and wondering why nothing sticks. The cascade does not reverse itself. Someone has to stop it.

1. Edmondson, A. C. (1999). Psychological safety and learning behavior in work teams. Administrative Science Quarterly, 44(2), 350–383. https://journals.sagepub.com/doi/10.2307/2666999 ↩︎