Terrible Leadership: A Stephen King Trilogy on Love, Grief, and Growth
THREE FILMS · SEVEN WEEKS · VIRTUAL INTENSIVE · COHORT-BASED · ONLINE · 1:1 COACHING
Leadership is an art of seeing. And it begins where certainty ends.…
The most consequential work of leadership often happens in the territory no training program prepared you for — the moments when you're asked to navigate complexity and ambiguity or hold unwanted loss and grief, while staying human inside systems designed to make that difficult.
Great novels and films can show us a path forward. They create the conditions to see what we normally defend against — and to do it alongside others who carry similar weight. But this is not a film club. It's a structured developmental experience that uses the art of cinema as a lens for the inner work of leadership. It can help develop more self-awareness, while seeing the larger systems we operate in, and how those influence — consciously or not — our authority, identity, and role.
So what can we learn from the “King of Horror” about leadership? These three films adapted from the work of Stephen King — Stand By Me, Pet Sematary, and The Shawshank Redemption — offer different explorations of identity, attachment, loss, grief, and containment. Through childhood, family, and friendship, these stories invite us to consider what happens when the people, places, roles, and worlds that have held us together can no longer do so. It could invoke terror — maybe even horror. Or it could show us the essence of being human…and what it really takes to lead human beings in human systems through change. It offers and opportunity to be curious, and find the courage to stay with what we might find.
Drawing on adult developmental theory, systems psychodynamics, grief literacy, terror management theory, existential philosophy, and the adaptive leadership tradition, each session pairs a carefully chosen film with guided reflection, live dialogue, and exercises designed to shift not just what you think, but how you see — yourself, others, and the systems in which we operate.
The program includes two 1:1 coaching sessions to begin and end the reflection.
THE ARC
Stand By Me
WHO ARE YOU BECOMING?
How do our roles and identity change over time — alone or with others? Who do we need or want to help, hold, and guide us on that journey, including to see us and witness the losses and sacrifice we experience in order to grow?
ACT 1
Pet Sematary
LIVING WITH WHAT’S GONE
How might we honor tradition, the past, and what’s gone? What role do people in positions of authority play in helping and holding others through loss and grief?
ACT 2
The Shawshank Redemption
CONTAINING OUR ANXIETY
What role do institutions, systems, and those leading within them play in our lives and work? How might they foster our resilience, hope, and meaning in the face of change, loss, and letting go.
ACT 3
THE EXPERIENCE
This seven-week developmental experience uses the films not just as case studies to analyze or stories with leadership lessons to extract, but as containers for exploring our own experience. Through reflection, group inquiry, and individual coaching, we’ll stay with what the stories evoke. Let’s become curious about what our responses to the stories, characters, and each other might reveal about how we encounter endings, uncertainty, attachment, and change in our own lives and leadership.
The work is in learning to see: ourselves, one another, what we hold onto, what holds us, and what might become possible when let go.
The nature of this work and the topics we’ll cover explore deep existential questions about the human condition. If you are living through particular personal difficulties, please consider whether his is the best time to join this cohort; this is designed as a learning experience and is not a substitute for personal psychotherapy.
Watch
Every two weeks, you will watch the assigned film, on your own time and at your own cost, with a guided viewing framework that sharpens your awareness and attention to see clearly with new perspectives.
Reflect
Written prompts invite you to explore what’s happening beneath the surface of the film — within and between the characters or groups — to encourage more insight and understand of your own identity, role, and leadership challenges. Individual coaching at the start and end of the journey helps to deepen your learning.
Gather
A live session brings the cohort together for organized dialogue. This is not film analysis, but rather deepens the reflection and learning individual and as a group — inviting different perspectives about how we see, hold, and exercise leadership. Our time together will NOT be recorded to create a candid and supportive learning environment.
Integrate
Along with your final 1:1 coaching session, we’ll connect as a group following the last discussion to reflect together on what’s emerging and how to apply the learning to the live leadership challenges you are facing right now.
THE AUDIENCE
This experience is designed for senior leaders, executives, founders, organizational consultants, and executive coaches who sense that the most important dimension of their leadership or work lies beyond technique. They sense something deeper. They are curious about developing their capacity to see clearly, hold complexity, and remain present when everything invites avoidance or another approach.
You do not need to be an expert in movies. You do need to be willing to be moved. To be curious. And let what moves you become material for your own growth.
Small cohorts (e.g., maximum of 12 participants), intentionally limited to protect the depth of the work.
THE DIRECTOR
This course is designed and directed by Brian Sano, an executive and leadership coach, organizational consultant, and leadership development facilitator working with leaders who want to go deeper — into how they see, how they lead, and what they're willing to face.
His work draws on adaptive leadership and participant-centered learning, adult development theory, systems psychodynamics and group relations, grief literacy, human-centered design, eastern and existential philosophy, and Miksang contemplative photography, organized under one idea: leadership is an art of seeing.
This work is also based on Brian’s own experience studying and exercising leadership for 20 years in U.S. federal government — SEC, DOJ, Treasury, State, CIGIE, PRAC — including the 2009 Bear Stearns criminal prosecution and leading in high-stakes environments and within temporary organizations, as well as in private practice representing international financial institutions.
He is a certified coach (PCC, CPCC), holds a J.D. (barred in NY and DC), and works with clients in the U.S., U.K., Europe, and internationally.
Your Investment
The course will happen online, including four, 90-minute group sessions over seven weeks, with guided discussion and reflection. Individual coaching is included to start and end the journey.
Pilot Cohort: October 26, 2026 — December 10, 2026; online discussions: Nov. 5, 15, 19, Dec. 3, 10 (12 pm — 1:30 pm ET)
Maximum number of participants: 12*
Investment: $1,750 (USD, VAT included)
*The course will be confirmed once we have enough participants for a meaningful learning experience.
Join the pilot cohort
Please provide the following information to submit your interest for this upcoming cohort. Once the course and your application are confirmed, you’ll receive a payment link and an invitation to book your coaching sessions.