Leading Through Loss
A Philosophy at the Crossroads of Leadership, Grief, and Organizational Change
Leadership is demanding. Physically. Mentally. Emotionally. But over my 20 years studying, investigating, and exercising leadership, including coaching and advising leaders at senior levels of their organization, I’ve seen it ask more of us than we might imagine. It asks us to hold others through grief and loss — sometimes as we’re experiencing it ourselves.
Most leaders, however, were not trained to hold the weight of what that asks us to carry — I certainly wasn’t. Not until I experienced grief and loss on my own leadership experience.
No one warned me about this. I had to learn about these pains of change myself, including how to help and hold others through the losses I and others were asking them to take on. I also learned how to hold their anxiety and witness their grief in the process — and the cost of not doing so.
Now, I create supportive spaces for people including senior leaders, teams, and organizations to help them develop more awareness and learn from what they’ve been unable to see alone — about themselves, about the systems in which they operate, and about what the situation actually requires.
Helping leaders hold what they were never trained to carry
Every significant act of leadership asks someone to give something up. A role. A team. A dream. A version of ourselves. A way of working that worked. A future we had counted on.
Regardless, most leadership programs ignore loss. Or, they treat it as a change management problem.
It isn't…it's grief.
And almost no leader has been trained to carry it — their own, their team’s, or their organization's.
But the leaders I work with rarely arrive thinking or talking about loss or grief.
They feel stuck, but see some way forward, even if it’s blurry. They’re hoping for some advice. More resilience. For new tools, frameworks, or training to get people on board with their new vision. There’s a need for change…to change. They’re seeking help with a restructuring that isn't working. A team who can’t stand to be in the same room with each other. A need for a new strategy or “strategic planning.” Or a former star is now underperforming since the strategy shifted. They’re questioning a promotion that was supposed to feel hopeful and instead feels unfulfilling. A relationship with a colleague, a boss, a board that's changed, and seems heavier than anyone is acknowledging. Balancing work and life seems impossible, especially with the needs of a new born child or ailing parent. There’s a sense that something has ended — though no one has said so aloud — and that they are supposed to just be keep going as if it hasn't.
But when we pause, slow down, and remain curious, something else usually comes into view. There has been a loss. Often several. The leader is carrying them, mostly alone, while continuing to show up for everyone else.
This is the territory of Leading Through Loss.
Leadership begins where certainty ends
WHAT LOSS ACTUALLY MEANS IN A LEADERSHIP CONTEXT
We tend to reserve the word grief for bereavement or death of a loved one. But that could be limiting our ability to lead.
David Kessler, collaborating with and extending the work of Elisabeth Kübler-Ross, has spent decades making the case that grief is the human response to any significant unwanted loss — not only death.
Relationships end. Identities are outgrown. Competencies become obsolete. Cultures shift. Roles are reorganized out of existence. Organizations pivot, and with every pivot, someone loses something they had built their professional self around.
These losses are real. Their pain is real. And so is the impact, even if we don’t see it.
They follow recognizable patterns. And when they go unnamed, they go underground — where they surface later as cynicism, disengagement, change fatigue, “quiet-quitting,” or the kind of performative resilience that organizations reward and that slowly amplifies the underlying problem.
For those in roles or positions of formal authority, the picture is more complicated still. A leader is frequently the person asking others to accept a loss — to give up a product, a team, a way of working, a piece of their identity — while also carrying their own losses from the same change. And, sadly, there is rarely a container for that leader's own grief. Regardless, they are expected to remain composed, decisive, provide answers, and move things forward — to drive results. But the grief doesn't disappear when we hit our strategic goals or KPIs. It lingers….
WHY LEADERS ARE OFTEN UNPREPARED FOR LOSS
Three things make this harder for people in positions of authority than for almost anyone else in the organization.
The first is training. Few, if any, business schools, leadership development programs, or coaching certifications meaningfully address grief. Leaders learn about power and influence. How to set strategy, manage stakeholders, communicate with impact or “executive presence.” Curriculums cover trust, psychological safety, and high-performing teams. They learn their leadership style. Or how culture eats strategy for breakfast. They might gain some insights into emotional intelligence or how others perceive them through 360 surveys. These are all important and can all be beneficial. But they don’t teach leaders how to sit with what is being lost while leading through change, or how to hold others in the process.
The second is the defensive architecture of organizations. The late British psychoanalysts Elliot Jacques and Isabel Menzies Lyth showed how institutions construct so-called social defenses against anxiety — routines, rituals, jargon, hierarchy — that protect the system from seemingly unbearable feelings and emotions. One of the things organizations most reliably defend against is grief. The forward-looking language of strategy. The relentless optimism and positivity crafted into change-related communications. The implicit instruction that professionals should get "on board" with the new direction. These are not just neutral norms. They are anxiety-management tools. They help the organization keep functioning. But they make it nearly impossible to name a loss while it is happening. They might hold us back, preventing real progress.
The third is existential. Terror Management Theory — a body of social psychology research developed by Jeff Greenberg, Tom Pyszczynski, and Sheldon Solomon and others, building on Ernest Becker's work on mortality awareness — demonstrates that when human beings are reminded of their own death, even subtly, they cling more tightly to their cultural world views, their self-esteem projects, and the structures that buffer them against that existential angst and anxiety. Organizational loss makes our mortality salient in many ways: the end of a role, the failure of a project, the need to upskill, the aging of a founder, the dissolution of a team, the announcement of layoffs — especially in the age of artificial intelligence (AI). Much of what looks like "resistance to change" in organizations is death anxiety in disguise. It might be unconscious, not yet seen or known. And leaders who cannot see this pattern mistake it for miscommunication, a motivation problem, or lack of engagement, leading them to apply the wrong tools.
Put together, these three present the conditions most senior leaders are quietly living inside: they’re asked to do developmental work they've never been trained for, inside systems designed to prevent that work from surfacing, while managing an existential undercurrent that almost nobody in the room is willing to name.
THE COST OF UNPROCESSED LOSS
But what’s at stake here? What’s the cost? When grief is not acknowledged in a system, it does not disappear. It metastasizes. Even worse, it is acknowledged but judged by others, known as disenfranchised grief.
Teams become cynical in ways that look like individual attitude problems but are actually collective grief with nowhere to go. Change initiatives stall because the people being asked to change have not been given space to let go of who or what they're being asked to leave behind. Leaders burn out — not from the volume of work, but from the invisible weight of the grief they are carrying on behalf of systems that refuse to name.
New cultures — built on values and behaviors — form from the losses nobody spoke about. The founder's departure. The layoffs that were announced as "restructuring." The product that quietly disappeared or the report that was shelved. The version of the company that existed before the acquisition. These unprocessed losses lurk in the shadows of an organization — unaddressed, but powerfully influencing what people think and feel and how they behave.
Leaders who cannot hold grief cannot lead change. They can announce change. They can implement change. But they cannot lead people through it. The difference shows up in retention, engagement, execution, and in the leader's own capacity to last.
Leadership is an art of seeing
WHAT IT LOOKS LIKE TO LEAD THROUGH LOSS
Leading through loss is not a technique. It is a quality of awareness. It requires intention and curiosity. Courage and care.
It begins with the willingness to name what is being lost — in a strategy announcement, in a reorganization, in a personal transition. Not to dwell there. Not to wallow. But to acknowledge, with clarity and compassion, what people are being asked to give up. That small act of witnessing, when done well, can change the emotional landscape of what follows.
It requires the leader to develop their own grief literacy — to recognize loss in its many forms, including the ones that don't look like loss from the outside. A promotion is a loss. A merger is a loss. A successful exit is a loss. The achievement of a long-held goal can be one of the most disorienting losses a leader or team ever faces.
It means creating what psychologist Donald Winnicott called a holding environment — a container strong enough for difficult feelings to be present and processed without being acted out. For leaders, this is both an internal capacity and an organizational practice. The internal capacity is built by doing one's own grief work. The organizational practice is built by modeling what it looks like to name a loss without collapsing into it. Leadership requires balancing challenge with support.
And it means understanding that, as Ronald Heifetz and his adaptive leadership framework puts it, the work of leadership is to disappoint people at a rate they can absorb or tolerate. Every complex, adaptive challenge asks people to let go of something. The leader's job is not to soften their loss into invisibility. It is to hold their attention with enough care and walk along side them through it — honestly, steadily, vulnerably, and with the kind of clear seeing that comes from having done the work oneself.
THE FRAMEWORK THAT SHAPES THIS WORK
My approach to Leading Through Loss draws on several intellectual lineages, woven together by twenty years of federal leadership experience and a practice rooted in the belief that leadership is an art of seeing.
The grief literacy comes from David Kessler and the tradition he carries forward from Elisabeth Kübler-Ross — especially Kessler's sixth stage of grief, finding meaning, which describes what becomes possible on the other side of loss that has been fully faced.
The existential dimension comes from Terror Management Theory and the broader existential philosophy tradition — Ernest Becker, Otto Rank, Rollo May, Kierkegaard, Sartre, de Beauvoir, Nietzsche, Heidegger, Camus, and others — that has shaped how I think about mortality, authority, and the defenses that organizations construct to manage death anxiety.
The interconnected lens comes from the Tavistock tradition of systems psychodynamics — Wilfred Bion, Eric Miller, Elliot Jacques, Isabel Menzies Lyth, Mannie Sher, Eliat Aram, and others — which offers the most rigorous account I know of how organizations collectively manage anxiety and how those defenses shape what is possible at the level of individual leadership.
The Adult Development frame derives from Robert Kegan's constructive-developmental theory — especially as studied and applied by Jennifer Garvey Berger and her colleagues — or vertical leadership development, which describes how adult growth happens. This is not through acquiring new information, but through seeing what we are often subject to and the power it has over us. Grief, and the eventual meaning we can see despite it, embodies this kind of developmental growth edge.
The leadership architecture comes from Ronald Heifetz's adaptive leadership framework — the distinction between technical and adaptive work, the discipline of holding steady in the heat, and the recognition that all adaptive change involves loss.
The internal defense systems also draw on Internal Family Systems — developed by Dr. Richard Schwartz and expanded on by others, including Dr. Frank Anderson — seeing an internal system of protective parts, each carrying important roles but also burdens. With that, we can reconnect to the ever-present energy, insight, and awareness that becomes accessible when we see and hold those parts with curiosity and compassion, rather than judgment, rejection, or resistance.
And the contemplative thread runs throughout, draws on my training as an student, instructor, and advisor at the Miksang Institute for Contemplative Photography — a perceptual discipline Michael Wood generated from the Tibetan Buddhist contemplative tradition. Miksang invites genuine awareness through direct perception and our inherent ability to see what is actually here, now, before our interpretation, beyond the story we tell ourselves about what we're seeing. It's the same capacity for clear seeing that every other lineage in this work points toward, arrived at through a different door of perception.
WHY THIS WORK, NOW
We are living through a period of compounding loss and anticipatory grief. Organizations are restructuring at incredible speed. Our careers and work are being reshaped by numerous forces — the COVID-19, remote work, a loneliness epidemic, AI, geopolitics and global conflicts, climate change, generational shifts in the workforce — that no strategic plan can fully absorb. Long-held identities are becoming obsolete inside the span of a single career. Public institutions are under pressures they were never designed to withstand. Human beings worry about their work and careers being replaced.
Leaders are being asked to hold all of this, and to keep holding it, often without any container for their own disorientation or development. Moreover, in budget cuts, training, learning, and development are often within the first line item to go.
In this environment, the capacity to lead through loss is not a “soft skill.” It is the skill. It is what separates the leaders who really understand change from the ones who are slowly ground down by it. It is what allows organizations to move through change and endings with integrity, rather than defending against them until the cost comes apparent elsewhere. It is being human.
The work is not about becoming comfortable with loss. It is about becoming capable of staying present to it — in yourself, in your teams, and in the systems you are trying to lead — long enough for meaning to emerge and growth to evolve.
HOW THIS SHOWS UP IN MY PRACTICE
The Leading Through Loss thread runs through my entire practice, though it takes different shapes in various offerings. Sometimes, it is apparent and named. Other times, it works silently at deeper levels in the background. In my various roles, I hold this lightly, with the intention and awareness to see how it might serve my clients — meeting them where they are, while also creating a container and environment in which they can explore deeper learning to find meaningful growth. Each approach offers a different doorway into the territory of loss, identity, and sense-making under the constant pressure of finding meaning and purpose in despite the limited time we have together.
In one-to-one executive and leadership coaching, this might involve the co-creating a trusted space over several months where a leader can sit with and see what they are carrying and the weight of that. This could be loss within their own changing role or identity. Or it might include what others are experiencing within a team, group, or across the organization or larger systems. Often, this might involve things they have not even seen or been able to name. Our coaching partnership can help see this clearly enough to lead through it rather than around it.
In leadership development cohorts and courses, my role involves serving more as a “guide on the side” rather than a “sage on the stage,” as Alison King described it. Besides designing the curriculum, learning objectives, and a pedagogy that aligns with those, I aspire to co-create a container and space for the group as a whole and each of us individually to question and process these principles and theories though in a way that is real and honest, but accessible. This could include group discussion and exercises, self-reflection, reading, and individual journaling. Coaching and assessments are typically offered before and in between the sessions.
Besides writing and teaching with case studies that explore the lives, work, and real-life dilemmas and challenges of prominent leaders in the public and private sectors, I also use creative approaches to facilitate leadership development. This might include film or novels to invite more curiosity, courage, and confidence to lead through grief, identity transitions, and organizational change. In fact, I’ve found that fiction and film can create a learning container in which leaders can be vulnerable enough to encounter the difficult truths of their own experience without direct exposure.
This artful approach often explores the more existential elements of leadership, asking what it means to be human. How does our humanity impact our leadership and work and vice-versa? Should we help others develop and grow just to produce better results in our organizations? What if our development was the end, and work was the means? How might we live, learn, and lead inside systems we did not design? How might we use leadership development to move the human race forward..?
In organizational consulting, my role might start with a request to help a senior leader, team, or organization with “change management” or to solve an issue related to their strategy, culture, or organizational health, including to develop a new approach or assess whether the culture and strategy are aligned effectively.
Quickly, I tend to find that success here depends on the willingness to name what an organization and its members might be grieving — the founder or senior leader who left, the strategy that failed or isn’t working, the culture that no longer exists, a fear of the unknown and the new ways of working or being that requires. What else…?
My work often helps people see how individuals, teams, or groups can find a way forward…despite those losses. Indeed, doing this deep work can help best prepare for whatever change or uncertainty might come in the future, even when I’m gone.