Executive Leadership Insights: Navigating Challenges in Nonprofit Leadership
Insights from Resilia's Unstuck AMA Series Panel Discussion
About This Session
Resilia brought together three experienced Executive Directors—Cheryl Wadlington (The Evoluer House), Kim Jones (Montgomery County Black Collective), and Tina LaRoche (Camp Holiday Trails)—for a candid conversation about the realities of nonprofit leadership.
With over 55 years of combined experience, these leaders shared honest insights about sustaining vision, building resilience, and navigating the unique pressures facing today's nonprofit sector.
The conversation, attended by executive directors and organizational leaders from the Resilia Community, revealed common threads that transcend mission and geography—
Isolation of leadership
Board management
Self-care
Yet the discussion also illuminated how a leader's intersecting identities shape their experience, particularly for women of color navigating systemic barriers while leading organizations serving marginalized communities.
The Loneliness at the Top
Executive leadership carries a weight unlike any other organizational role. Board members have each other as peers. Staff share similar positions. But the executive director stands alone, making decisions that ripple throughout the organization with no immediate colleague to turn to for support.
This isolation intensifies during crises—when funding falls through, when difficult personnel decisions must be made, or when external forces threaten organizational stability.
For leaders of color, particularly those leading organizations centered on Black communities, these burdens compound. The nonprofit sector's funding landscape reflects broader societal inequities—Black-led organizations receive less funding, face more scrutiny, and must work harder to establish credibility. Leaders described fighting for basic respect and confronting bias both subtle and explicit.
These challenges create real trauma that executive directors must process while continuing to lead. The physical toll emerged as a recurring theme, with leaders sharing experiences of stress-related illness and the intensified pressures of the current political climate.
Self-Care as Strategy, Not Luxury
Self-care has evolved from optional to essential for nonprofit leaders. Yet the approaches that work tend to be practical rather than aspirational—comforting entertainment, brief meditation practices, creative outlets. The key is identifying what genuinely provides mental rest within demanding schedules.
Leaders were candid about the gap between discussing self-care and practicing it. The sector's culture of martyrdom runs deep, with many working through vacations and pushing past physical warning signs until crisis forces change. Yet there's growing recognition that this approach is unsustainable.
After experiencing serious health consequences, many leaders reach a turning point where protecting their wellbeing becomes non-negotiable—a shift that serves both leaders and the organizations they steward.
Keeping Vision Alive Amid Daily Fires
Leaders maintain connection to long-term vision through complementary approaches. Keeping the people served at the absolute center of every decision provides a north star that cuts through organizational politics. Understanding organizational life cycle is equally crucial—young organizations cannot take on the same initiatives as established institutions. This requires discipline to decline opportunities that would stretch capacity beyond sustainability.
Regularly experiencing the mission firsthand helps leaders stay grounded. Taking meals with participants and staff, attending programs, or creating informal moments to reconnect with why the work matters fills leaders' cups while keeping mission at the forefront. The conversation also surfaced the value of celebrating what's working rather than only identifying problems.
The Perpetual Challenge of Governance
Board management requires constant attention and rarely feels fully resolved. Many leaders observe that composition typically follows a rule of thirds: one-third highly engaged board members, one-third finding their footing, one-third minimally participatory.
Direct, honest communication about expectations often yields better results than subtle hints. When board members aren't leveraging networks or meeting commitments, sometimes they simply need explicit asks. Some executive directors invest in external governance consultants to create neutral third-party accountability. Another strategy involves including program alumni and family members on boards, ensuring those closest to the mission have decision-making power.
Building and Sustaining Teams
Staff management requires similar intentionality. Intensive onboarding that establishes values, self-care practices, and open-door policies creates the foundation for a healthy culture. When leaders model vulnerability, it creates space for staff to do the same.
Beyond recruitment, retention demands attention to compensation. Leaders described advocating for living wages, pushing back against relying on mission passion in lieu of fair pay. Organizations that invest in team activities strengthen relationships and demonstrate how they value people. Regular check-ins help surface concerns before they become crises, with some organizations explicitly teaching interdependence as a value.
Starting Without Resources and When Values Conflict
For leaders without established fundraising networks, the starting point is simple: reach out to everyone you know and ask for three names of others who might be interested. Leaders suggested prioritizing corporate sponsorships over foundation grants initially—a one-page letter and meeting often moves faster than lengthy proposals.
Authenticity in relationship-building matters more than polished pitches. Small moments of genuine interaction can evolve into meaningful partnerships over time.
When board members or staff bring professional assets but demonstrate values that contradict organizational principles, the response was unequivocal: values cannot be sacrificed for capability. Working with people who perpetuate oppressive dynamics creates a burden that already-stretched organizations cannot afford. When direct conversations don't shift behavior, transition becomes necessary. Protecting the mission and wellbeing of staff and participants must take precedence.
Moving Forward:
Sustainable nonprofit leadership requires acknowledging its costs, implementing practical self-care, maintaining clarity about mission and capacity, building authentic relationships, and making difficult decisions when values diverge. With community support, strategic thinking, and commitment to both mission and personal wellbeing, it's possible to lead with effectiveness and joy.
Resilia is grateful to Cheryl Wadlington, Kim Jones, and Tina LaRoche for their generosity in sharing their experience and insights with and alongside our community.
