On leadership, the grief of disconnection, and what it takes to build institutions that remain human.
Someone recently asked me how the executives at my organization stay connected to the work.
I stumbled through an answer.
It was a fair question, and one I should have been prepared for; I have spent years building an organization around the very problem it seemed to describe. What caught me off guard, I think, was the distance the question assumed.
We have become accustomed to leadership existing somewhere apart from the work. The people making decisions are expected to operate at a higher level, where individual experiences become trends, relationships become reporting structures, and complicated human realities are translated into something manageable. There are good reasons for this. An executive who cannot distinguish the needs of an institution from the needs of any one person will struggle to lead it.
But somewhere along the way, distance from the work became confused with the capacity to lead it. And we have built an extraordinary number of institutions around that confusion.
What gets lost on the way up
I founded Kind Therapy Inc as a therapist.
In the early years, I conducted our new-client intakes myself. Those conversations taught me how differently an organization can look from the perspective of someone seeking its services.
Today, our master's-level interns conduct those intakes, while I continue to maintain a clinical caseload alongside my responsibilities as Founder and CEO. I have also intentionally structured our clinical supervision around smaller, consistent networks, preserving the continuity and trust that can so easily disappear as organizations grow.
These choices reflect different ways of approaching the same problem.
Some responsibilities needed to move away from me. Others I have chosen to retain. And some required structures that would allow people to remain known to one another as the organization grew.
I was not trying to keep Kind small, nor was I interested in growth for its own sake. I wanted to expand access to therapy for people who could not otherwise afford it, without losing the relationships that make care possible: the dignity of being known, the trust built through continuity, and the ability of those closest to the work to shape how it is done. None of these should become privileges dependent on the attention or goodwill of those at the top.
There is a difference between knowing how many people an organization serves and knowing what it feels like to seek its services. Between reviewing a staffing report and understanding what an ordinary workday requires of the people represented in it. Neither kind of knowledge is sufficient alone. The trouble begins when one is treated as more legitimate because it is farther from the experience it describes.
A budget can be accurate and incomplete. So can an employee survey, a performance review, or a strategic plan. The numbers may tell us what happened. The people living with the consequences may know why.
The people who stop explaining
I have been thinking about the grief that accumulates when institutions repeatedly fail to recognize what people know.
A patient tells their story again because the previous telling did not travel with them. An employee identifies a problem, watches it become a committee discussion, and eventually encounters the proposed solution as another requirement added to their day. A manager learns that raising concerns will make them responsible for resolving problems they lack the authority to change.
At first, people try harder. They explain more carefully. Document what happened. Find the appropriate person. Learn the language of the institution.
Then something changes.
They become quieter.
We may call this disengagement, cynicism, or resistance. Sometimes those descriptions are appropriate. But sometimes we are witnessing the consequences of a person learning that participation has become expensive.
Research on workplace connectivity offers one example. A 2026 systematic review found that expectations of after-hours availability were generally associated with poorer psychological detachment and greater strain. The finding concerned expectations, not simply whether people used technology after hours. An employee may be told they are free to disconnect while learning that the people who remain available receive greater recognition. Both things can be true.
The same contradiction appears in research on workplace mistakes. A study of UK financial-services professionals found that women felt less comfortable than men acknowledging mistakes, especially on teams dominated by men, though both expected the same formal penalties. The study cannot establish why. It does show that knowing the rules is not the same as trusting what will happen when you rely on them.
Trust is built through experience, not assurances. An institution can formally welcome honesty while its everyday responses teach people to fear the consequences of being honest. Over time, that contradiction changes how people participate. Curiosity becomes caution. Generosity becomes self-protection. Knowledge that might have strengthened the organization remains unspoken, not because people have stopped caring, but because they no longer trust that their care will be received without cost.
We call the result disengagement, as though it began with the individual. We measure what people have withdrawn without examining what taught them to withdraw.
The work that never disappeared
There is a temptation to believe that better technology and more sophisticated organizational design will solve this distance. They may help. I use both. But efficiency has a peculiar way of making responsibilities appear to disappear when they have merely changed hands.
A 2026 case study of an organization operating without conventional middle-management layers reported that the functions of management remained necessary. Coordination, support, resource allocation, and organizational development were carried through alternative roles, shared practices, and self-managing teams.
The organization had changed where authority lived. It had not abolished the work required to make collective life function. Understanding this matters as AI accelerates the production of decisions.
A system can generate an operating model without knowing the history of every relationship affected by it. It can identify a redundant process without understanding the failure that originally made the process necessary. The recommendation may be intelligent. The savings may be real. And the person responsible for implementing it may still recognize something the analysis cannot see.
Recent research on algorithmic scheduling illustrates how organizational efficiency can coexist with diminished control over personal time. In a study of hotel employees, greater exposure to automated scheduling was associated with lower working-time control, more work/family conflict, and greater burnout-related strain. Supportive supervision weakened some of those associations.
The study was observational. It cannot prove that scheduling technology caused the reported outcomes.
But it asks us to consider something that conventional efficiency measures often leave out.
When an organization becomes more efficient, whose life becomes easier?
And whose life becomes more difficult to arrange?
The Conference Board's recent research on AI-enabled leadership raises related questions about unclear decision ownership and the need to preserve human judgment as work changes.
I do not think the problem is that machines are beginning to think.
I think it is that organizations can become increasingly capable of producing answers without becoming equally capable of receiving the knowledge needed to judge them.
When care becomes the operating model
There is another danger in trying to build something different.
When you have seen what institutional distance can do to people, you may become determined never to reproduce it. You remain available. You remember the details. You take the difficult conversation. You make the exception because you understand the circumstances that make the exception necessary.
At first, this can look like unusually attentive leadership. It may even be unusually attentive leadership.
But there is a point at which the person trying to build a humane institution becomes responsible for personally compensating for everything the institution has not yet learned to carry.
The expectation can be affectionate. It can come from colleagues who trust you, employees who need you, or a community that has experienced too many organizations unwilling to listen.
The expectation can also take root in your own sense of responsibility. You have witnessed what happens when institutions abandon people, and you are determined not to reproduce that harm. So you intervene where structures fail, absorb responsibilities that have no clear home, and protect others from consequences they did not create. Over time, the institution learns to depend on your intervention rather than confront the conditions that make it necessary. Your competence becomes a substitute for institutional accountability, and what appears to be exceptional leadership may be evidence of a system that has never learned to carry its own responsibilities.
I have had to examine this in myself. There is a familiar idea that good leaders should be willing to do any job in their organization, including cleaning the floors. I agree that no work becomes beneath a person because of their title. But respecting every kind of work does not mean becoming responsible for performing all of it.
An executive who cannot tolerate ordinary work has misunderstood leadership. An executive who must perform every kind of work has not built a sustainable institution. Personal sacrifice can conceal organizational weakness for a remarkably long time.
A capable person fills the gaps. They preserve relationships, remember what has not been documented, and absorb the consequences of decisions made elsewhere. Their competence becomes evidence that the organization is functioning. Until they stop. And the institution discovers that something it believed belonged to the system had been living inside a person.
The tyranny of comparison
I have noticed another cost of trying to build institutions differently.
So much of the work can become organized around what we are refusing to reproduce.
We explain why a familiar practice is inadequate. Defend an unusual structure. Justify the resources required to preserve relationships that a conventional efficiency model might consider unnecessary.
We become fluent in the failures of the institutions that came before us. And sometimes, without realizing it, we allow those institutions to determine the terms of our imagination.
The work becomes a continuous argument against something.
I understand why. Companies that concentrate authority, obscure responsibility, or normalize human exhaustion can cause profound harm. Their influence does not disappear because we have decided to work differently.
But I have become increasingly interested in what happens when we stop organizing our aspirations around the failures we inherited.
What would we build if we were not perpetually defending the legitimacy of building it?
This does not mean escaping accountability. A different organizational model deserves scrutiny precisely because it claims to offer something worth sustaining. Nor does it mean that smaller teams, flatter structures, or more compassionate leaders are inherently better.
A small organization can concentrate power just as effectively as a large one. Decentralization can become abandonment. Flexibility can conceal constant availability. A mission can become a justification for asking people to give more than they can sustain.
There is no organizational form that makes human judgment unnecessary. The task is to keep designing, observing, and correcting the relationships through which power and responsibility are exercised. To be less interested in appearing different than in discovering whether the difference holds.
What our measurements cannot tell us
I think institutions are often most vulnerable where they appear most confident.
We know how to count services, revenue, retention, output, and time. We are less certain how to account for the human conditions that make those outcomes possible.
A recent review of organizational assessment research found that studies frequently established conventional psychometric validity while giving comparatively less attention to justice-related questions about how measurements are interpreted and used. That is a technical finding with a deeply human implication. We can become very good at measuring people without becoming equally good at understanding what our measurements mean for them.
An employee who no longer offers ideas may receive a lower engagement score. The instrument may be working exactly as designed. It may tell us very little about the experiences that taught the employee to stop speaking.
A leader who works extraordinary hours may appear productive, committed, and indispensable. The measures may be accurate. They may also be describing an organization that has failed to distribute responsibility.
Measurement is necessary. So is the humility to recognize its boundaries. The purpose of an institution is not to produce a convincing account of itself. It is to remain answerable to the reality of what it does.
The distance between us
I have returned to the question that caught me off guard.
How do the executives at Kind stay connected to the work?
I could have answered by describing my clinical practice, our supervision networks, or the ways responsibilities have changed as the organization has grown. Those are meaningful choices. They are also incomplete answers.
I have come to think that connected leadership is not principally about how often an executive returns to the front lines.
It is about whether the institution has preserved the means for people closest to its consequences to influence the conditions producing them.
Whether a concern can travel upward without losing its meaning. Whether responsibility can move outward without becoming abandoned. Whether people can remain known without being dependent on the attention of one unusually conscientious leader. And whether those entrusted with authority remain willing to encounter realities that complicate the stories they tell about their own success.
I do not believe the answer is to abolish distance. Leadership requires perspective, and perspective sometimes requires stepping away from immediate demands. But distance should serve understanding, not protect us from it.
There is grief in what happens when institutions lose that perspective. In the people who stop explaining, the professionals whose judgment no longer reaches decisions, and the leaders who exhaust themselves trying to bridge every gap personally.
I do not want that grief to become the organizing principle of our future. I want us to become more interested in what we can build than in endlessly demonstrating the failures of what already exists. I want institutions capable of carrying care without requiring anyone to become inexhaustible. I want the people who understand the work to have meaningful influence over how it is organized. And I want leadership to be measured, at least in part, by what becomes possible without the leader's constant intervention.
Perhaps that is why I struggled to answer such a simple question. I was being asked how executives remain connected to work, when I had spent years questioning why we had designed leadership to become separated from it.
I still see clients. Other people now carry responsibilities I once held. Our organization continues to change, and I continue to discover where our design falls short of our intentions. I cannot know every experience within it. I should not have to. The work is to build an institution capable of knowing what I cannot, and of responding without waiting for me to know it.
The distance between leadership and the work should never become the distance between power and responsibility.
Research Behind This Essay
The following research informs the essay's examination of organizational design, autonomy, measurement, and institutional accountability. These studies use different methods and populations; none independently establishes the broader Work Ecology framework.
Martela, F., Mäkkeli, J., & Kostamo, T. (2026). The ten functions of middle managers: Identifying their functional substitutes in a decentralized organization without traditional middle managers. Journal of Organization Design.
https://doi.org/10.1007/s41469-026-00207-w
A qualitative case study of how a decentralized organization redistributed managerial functions through self-managing teams, shared practices, and supportive roles.
Geldof, L. T. D., et al. (2026). The association between organizational culture and climate elements on W-ICT (non-)use outside working hours and employee psychological wellbeing: A systematic review of qualitative and quantitative studies. Frontiers in Organizational Psychology, 4.
https://doi.org/10.3389/forgp.2026.1919818
A systematic review examining organizational expectations surrounding after-hours digital connectivity and their associations with employee wellbeing.
Lordan, G., & Will, P. (2026). Is it ok to make mistakes at work? Perceptions of differential treatment of mistakes by men and women in the workplace. Frontiers in Organizational Psychology, 4, 1619562.
https://doi.org/10.3389/forgp.2026.1619562
Survey research examining differences in perceived psychological consequences of acknowledging workplace mistakes.
Wang, M., & Kunasekaran, P. (2026). When algorithms set the roster: Algorithmic scheduling, work-time control, and work-related burnout among hotel employees. Frontiers in Psychology, 17, 1958975.
https://doi.org/10.3389/fpsyg.2026.1958975
A cross-sectional study linking exposure to algorithmic scheduling with working-time control, work–family conflict, and burnout-related strain.
Amursi, E., Devine, M., & Abraham, P. (2026). Leadership disrupted: Preparing for an AI-enabled workplace. The Conference Board.
https://www.conference-board.org/publications/leadership-disrupted-preparing-for-an-AI-enabled-workplace
Institutional research examining AI-enabled leadership, organizational redesign, accountability, and human judgment.
Bazzoli, A., Vo, T. T., Campillo-Martínez, A., Downey, A. N., Pires Gifford, L., & French, B. F. (2026). Building justice-informed validity arguments in organizational psychology: Where the evidence is (and isn't). Frontiers in Organizational Psychology, 4, 1861006.
https://doi.org/10.3389/forgp.2026.1861006
A review of 63 organizational-assessment studies examining the evidence used to establish measurement validity and the extent to which justice-related considerations are incorporated.
