OCTOBER 5–8, 2026
An immersive four-day gathering where social sector leaders come together to reflect, connect, exchange ideas, close the year with intention, and support one another in a plan for the coming year.
The Cobb Mountain Leadership Retreat was created around one simple belief: today’s most effective leaders don’t lead alone.
Across nonprofits, philanthropy, public service, advocacy, community development, and mission-driven organizations, leaders face increasingly complex challenges. This retreat creates space to step away from daily demands, think alongside peers, exchange practical insights, and return with renewed clarity and stronger relationships.
Unlike traditional conferences, this is an intentionally intimate gathering where every participant contributes to the conversation.
Social sector leaders are doing some of the most important and demanding work in our society. They are navigating staff burnout, an unsteady funding environment, political divisiveness, community trauma, and organizational complexity, often simultaneously and with limited peer support. Yet the nature of this work tends to keep leaders siloed: in their own organizations, their own issue areas, their own geographic communities.
The Cobb Mountain Leadership Retreat is built on a simple conviction: that when social sector leaders have dedicated time and space to connect with one another, to share what’s working, wrestle with what isn’t, and be inspired by peers across sectors and communities, the quality and impact of their leadership grows.
This is not a conference. There are no vendor booths, no passive panels, no sessions designed for one-way information delivery. It is a gathering: intimate, participatory, and grounded in the belief that the people in the room are the primary resource. The outcome of four days is to advance a project of your choosing. You commit to working on yours and helping others with insights for theirs.
Learn directly from experienced leaders through open conversations rather than presentations.
Build authentic relationships with professionals across organizations, sectors, and communities.
Take intentional time to evaluate the year, prepare for what's next, and develop a clear leadership plan.
Recharge in a peaceful natural environment designed to inspire creativity, focus, and personal wellbeing.
Create conditions for genuine peer-to-peer learning, where leaders share strategies, challenges, and innovations across organizations and issue areas.
Spark new thinking through curated conversation, compelling facilitation, and the energy of being in community with passionate, purpose-driven people.
Give leaders dedicated time to reflect on where the year has taken them, close it well, and think clearly about what comes next.
The retreat culminates with you delivering your plan for the year forward. You’ll work on it throughout the retreat and support others with their plans. It’s the core goal of the retreat. We’ll present our plans on the final day and give one another feedback.
The retreat is open to leaders across the social sector, broadly defined. We welcome executive directors, CEOs, board members, development professionals, operations leaders, program leaders, foundation officers, philanthropy leaders, community organizers, government service leaders, and social entrepreneurs. Participants may come from established institutions or emerging organizations, from large urban nonprofits or small rural ones.
We welcome leaders at all career stages, from seasoned executives to mid-level leaders. Exceptional early-career professionals will be considered.
What unites participants is not a shared issue area or geography, but a shared commitment: to doing good work well, supporting your peers, and to growing as leaders in service of that work. We are intentional about building a cohort that reflects the full diversity of the social sector: across race and background, geography, career stage, organizational size, and issue focus.
We believe the greatest resource at the retreat isn't the speakers—it's the people in the room. Programming is designed to encourage participation, honest discussion, peer coaching, and collaborative problem-solving rather than passive learning.
The retreat is intentionally small and focused. Capacity is limited to ensure every participant can contribute meaningfully, be known by the group, and leave with real relationships rather than a stack of business cards. Participation is by application only.
We intentionally build a cohort that reflects the diversity of today's social sector across:
Different perspectives create stronger conversations and better leadership.
Step away from the daily demands of leadership and invest four days in reflection, connection, and renewal alongside peers committed to creating meaningful impact.
