News
Each year, the Connecticut Land Conservation Council convenes land trust executive directors from across the state for a day of connection, candid conversation, and peer learning. The 2026 Executive Director Retreat continued that tradition — and, in many ways, deepened it.
Land trust executive directors can often feel isolated in their roles. Many are the only staff member in their organization, or one of just a few. Even in larger organizations, the responsibility of leading a land trust — navigating boards, fundraising, stewardship obligations, staffing, and evolving community expectations — can feel weighty and, at times, solitary. The annual retreat provides a valuable opportunity to step out of that isolation and into a room of peers who uniquely understand both the challenges and the rewards of the work.
This year’s retreat was especially meaningful because it marked the first time we hosted the gathering on-site at a land trust property. We are deeply grateful to Flanders Nature Center & Land Trust for welcoming us to their campus in Woodbury.
The setting added something special to the day. With clear skies and fresh snow on the ground, participants were able to spend part of the lunch break outdoors — walking Flanders’ accessible trail, learning about the property, and visiting their maple sugaring operation. Being together on conserved land served as a powerful reminder of why this work matters.
Surfacing Shared Challenges
The retreat began with a full-group discussion in which each executive director shared a pressing challenge they are currently navigating, or a topic they hoped to learn more about from their peers.
Several themes quickly emerged.
One major thread was growth — specifically, how to grow sustainably. Many land trusts represented in the room are in a period of expansion. They are hiring staff, increasing budgets, stewarding more land, and broadening programming. With that growth comes a host of questions:
How do we fund new positions responsibly?
What should the next hire be?
How do we design organizational structures that support both staff and mission?
How do we prevent burnout — for staff and for ourselves?
Closely related was the question of “right-sizing.” Even in a growth phase, executive directors recognized that expansion has limits. Service areas, conservation opportunities, and community capacity all shape what scale makes sense. Determining the appropriate level of staffing and operational capacity — especially in a changing conservation landscape — was a recurring theme.
Another significant topic was the evolving mission of land trusts. Many leaders noted that traditional conservation opportunities in their service areas are becoming fewer. That reality is prompting deeper reflection:
What does the next phase of land trust work look like?
How do we engage new constituents and younger audiences?
How do we ensure our organizations are inclusive and equitable — both internally and in how land is used within our communities?
The conversation was enriched by the diversity of perspectives in the room. Executive directors from highly suburbanized and urban landscapes shared insights alongside those working in more rural regions of the state. Some participants had been in their roles for only a few months; others had served their organizations for nearly two decades. That range of experience — across geographies, landscapes, and career stages — is always one of the retreat’s greatest strengths.
Breakout Conversations: Space for Deeper Dialogue
After lunch and time outdoors, participants divided into smaller breakout groups focused on three broad themes: fundraising, staffing and organizational growth, and collaboration.
Rather than diving into technical details, these sessions created space for candid exchange. Executive directors compared approaches, shared lessons learned, and reflected honestly on what feels challenging in their current season of leadership. The conversations reinforced that while each land trust operates in a unique geography and community, many are navigating similar questions about sustainability, growth, evolving missions, and long-term capacity.
In the fundraising discussions, leaders explored how to build durable support systems for their work. In the staffing conversations, the focus turned to organizational culture, succession, and how to grow without losing sight of well-being. And in the collaboration breakout, participants reflected on how partnerships can help land trusts adapt to changing landscapes and limited resources.
What made these sessions meaningful was not any single tactic or takeaway, but the opportunity to speak openly with peers who understand the complexity of the role. The value of the retreat lies in that space: time set aside to step back, compare experiences, and think collectively about what comes next.
Carrying Conversations Forward
We closed the day by asking each executive director to name one idea they wanted to follow up on — and one person in the room they planned to connect with after the retreat.
Not surprisingly, every participant identified at least one conversation they hoped to continue. That, perhaps, is the clearest indicator of the retreat’s value.
The Executive Director Retreat is not designed to produce a single consensus or formal resolution. Instead, it creates space for honest exchange, shared problem-solving, and renewed connection. Those conversations — sparked in a meeting room in Woodbury and continued on snowy trails — will ripple outward in the weeks and months ahead.
We are grateful to the leaders who made time in their busy schedules to participate, and to Flanders Nature Center & Land Trust for hosting us so generously.
We look forward to gathering again next year.
