What a Peer Learning Circle Made Possible for NYC Leaders and Us

During Ericka and Trish’s time in philanthropy, our communities have been navigating increasingly rough terrain: a global pandemic, a racial justice awakening, and existential threats to democracy. The conditions could not be more ripe for funders to embrace our responsibility to serve as risk capital and do all that we can to give our partners what they need to carry out strategies that will move us through what is currently happening.

Working at the Robert Sterling Clark Foundation (RSCF), a place with a deep commitment to practicing trust-based philanthropy, has afforded Ericka and Trish the opportunity to experiment with how to best show up for our partners, and in ways that honor the incredible work they are doing. One of the ways we do this is through formal practices of deep listening, learning, and responding to what we hear from our grantees, and we are grateful for the many ways our partners give us the opportunity to improve through holding us to our own expectations of transparency and mutual accountability.

One of the most powerful sources of improvement was cultivated through a partnership with the Leadership Learning Community (LLC), where Ericka was the Co-Executive Director, alongside Nikki, before joining the RSCF team. What we initially thought would be a one-off virtual gathering of the Executive Directors that lead the foundation’s grantee organizations turned into a peer community that continues to this day, where people engage in acts of reciprocity centered on a simple question: how can we ensure we all have what we need?

We are sharing what we’ve learned so far through this long-term experiment because it shines a light on the experiences of isolation and overwhelm that nonprofit leaders often face and has helped us gain clarity on what philanthropy’s role can be in providing “support beyond the check” that directly enables these leaders to build resilient teams and organizations.

Listening

Since 2020, the Executive Director Learning Circle has been a loosely facilitated space of confidence, trust, and peer support that meets with a flexible frequency in alignment with how the context and conditions are evolving. From the funder perspective, it is crucial to balance our role as the convener with the role of the Executive Directors to set the agenda and shape the space, which is why we invited one of our field building grantee to facilitate it.

The foundation approached LLC because we knew Ericka’s facilitation style would offer the right blend of openness and grounding that would support the Circle participants to build authentic relationships and find their purpose quickly. We felt fortunate that she agreed, even though she was navigating her own pandemic-induced challenges like everyone else. Her facilitation and deep care created a model that has lasted well beyond that crisis, and become a standing space that supports our partners through personal, organizational, and community-wide issues. LLC typically focuses on connecting leaders in the field nationally, and we were grateful that Ericka responded to this local-scale need and held the space so thoughtfully.

Learning

Ericka’s transition to the RSCF staff prompted a shift away from LLC as facilitators of the circle and a reflection on the learnings from their time holding the space.

According to LLC, the conversations that took place in the Circle ranged from post-election strategy and managing staff burnout to operationalizing anti-racist principles and reshaping funder relationships. It would be impossible to summarize the richness that was generated over five years, so instead LLC offered three persistent themes:

Leading in perpetual crisis: Executive Directors consistently reported feeling pressure to balance visionary work against the administrative and managerial burdens of leading a nonprofit, and becoming overwhelmed by unending demands that shifted from manageable stressors to a constant, chaotic barrage. They struggled with burnout from exhaustive pacing and recognized the urgency of prioritizing self-care and rest as a radical strategy for sustainability and more purposeful, centered leadership.

The paradox of leading a social-change organization while sometimes being seen by staff as representatives of oppressive systems (e.g. the nonprofit industrial complex) led the circle to explore ways to embody shared and distributed leadership, moving away from micromanagement and “lone hero” models. The consensus was that being an Executive Director is a lonely position, which underscored the critical need for this circle — a place to be among peers, practice vulnerability, and seek help and solutions.

Operationalizing equity and collective liberation while shaping organizational culture: LLC encourages leaders to just work in just and joyous ways, because the ‘how’ is just as important as the outcomes. Conversations in the Circle repeatedly focused on moving from talking about anti-racist values to practicing them through structural change and intentional leadership. This showed up in the strong desire for transparent and equitable human resources practices, such as compensation structures or salary bands that reduce the subjectivity of negotiation and support pay equity. Having values-aligned structures becomes even more important during crises because it allows for the organization to serve as a space of stable footing in the midst of so much external uncertainty.  

A perspective LLC offered the Circle is that building and maintaining trust is an antidote to staff anxiety, and doing so requires consistent, clear communication about the organization’s financial and operational realities. Effective supervision was redefined as a supportive function that focused on coaching, development, and checking on people’s emotional well-being — not just task management. Participants recognized that genuine anti-racist and culture-shifting work is messy and requires a commitment to unearthing discord, conflict, mending, and healing. They noted the importance of having a shared language and external facilitators to help staff navigate conflict and challenge white supremacist practices baked into traditional work models.

Strengthening connectivity in leadership infrastructure: The exclusive and confidential structure of the Circle enabled a secure platform for leaders to rapidly share high-stakes, real-time information and collectively problem solve during volatile periods. Over time, the group co-created a Resource Bank that included vetted resources, tools, tips, and consultants that included topics like financial modeling, budgeting approaches, security, human resources guidance, and ethical AI platforms, which saved time and reduced organizational risk. Through individual check-ins and cross-organizational conversations, leaders in the Circle came to better understand each other’s work and open up possibilities for partnership and collective action that have a direct impact on leadership infrastructure in the region and across movements.

Responding

“We view the process of changing together as an essential step toward transformation,” said Nikki, Executive Director of LLC, who also spent time facilitating this circle. “We have to slow down in order to take strategic action. This means cultivating the space and grace needed to embrace habits and pathways that prioritize collaboration, collectivity, and interdependence. Learning together is a pathway to how we grow into collective liberation.”

Facilitating the Circle gave Ericka the chance to learn about the conditions, concerns, approaches, assumptions, and mindsets of diverse leaders over time. She started to see patterns, connect dots, and observe the importance of community-led spaces that are free of judgement. It also was a place to practice liberatory facilitation that involves ego-light leadership, deep listening, and the release of control through the encouragement to “rebel” and say “no” to ensure consent is real. The positive reception of this facilitation style conveyed a sense of legitimacy that we will carry forward.

As 2026 begins, some strategies toward our vision of a just, equitable, and vibrant New York City feel evergreen, while others will need to adapt from moment to moment. That’s why we are committed to staying in a learning stance and supporting our grant partners to do the same. Spaces like the Circle offer mutual aid, but they also foster growth through shared learning. Our partners tell us that beyond the funding they receive, having spaces to step back, reflect, and strategize amid complexity is more critical than ever in times like these.

See other posts in this series for more on what we’re experimenting with and what we’re learning along the way.