Connected at the Top: Rethinking Support for Nonprofit Leaders
By: Angela Fenton, Systems and Professional Development Coach
“It’s lonely at the top.”
We’ve all heard this phrase, often used in reference to top-of-the-house leaders like senior leaders in nonprofit organizations. Not “lonely” in the obvious sense of being isolated or unsupported, but in the quieter way that comes from holding responsibility that cannot easily be shared. Executive Directors are surrounded by people every day, yet often lack spaces where they can speak openly about the doubts, tensions, and unfinished questions that come with the role. Over time, many learn to carry these things privately, assuming this is simply part of the job.
This experience is particularly common in the nonprofit sector, where leadership is closely tied to purpose and values. Decisions rarely feel neutral, and the stakes often feel personal. Executive Directors are accountable to boards, staff, funders, and communities, all while navigating limited resources and increasing complexity. For women and gender-diverse leaders, these pressures are frequently compounded by expectations around emotional availability, steadiness, and resilience. Many leaders feel an unspoken responsibility to absorb uncertainty and protect others from it.
What is striking is how often leaders believe their experience is unique. They look around and see capable peers who appear to be managing just fine. They conclude that their own moments of self-doubt or fatigue must reflect a personal shortcoming, rather than a common feature of the role. This assumption keeps many leaders silent at precisely the moments when connection would be most helpful.
In my work hosting Executive Director Coaching Circles, I see this dynamic play out consistently. These circles are intentionally structured peer spaces where nonprofit Executive Directors come together to reflect on real leadership challenges, practise deep listening, and learn from one another without the pressure to perform or provide advice. What participants most often comment on is not the answers they receive, but the relief of being able to speak honestly with others who understand the role from the inside.
When nonprofit leaders are given the opportunity to speak candidly with peers, a different narrative begins to emerge. Again and again, leaders remark on how similar their challenges are, despite differences in organizational size, mission, or career stage. One experienced Executive Director reflected that hearing the struggles of newer leaders reminded them of their own early years in the role. What surprised them was not the content of those struggles, but the realization that they had underestimated how much they themselves had grown. That perspective did not come from advice or comparison, but from listening and recognizing familiar patterns.
Another leader, new to the nonprofit sector but with significant experience in senior private-sector roles, described being caught off guard by the nuanced demands of the Executive Director position. Despite technical competence and leadership experience, the role surfaced questions that felt unfamiliar and difficult to articulate. Being connected early with peers who had lived experience of the role helped normalize those questions and shifted how this leader understood meaning in their work. Not only in relation to the mission itself, but in how they chose to show up and lead day to day.
These kinds of insights rarely surface in traditional leadership settings. In many professional environments, leaders are rewarded for decisiveness and problem-solving. While these skills are essential, they can crowd out opportunities for reflection. Peer-based spaces designed around listening and inquiry allow leaders to slow down and think more clearly. They offer something distinct from mentoring or consulting. Rather than focusing only on solutions, they create room for leaders to explore how they are experiencing their work and what that experience is revealing.
For many leaders, simply hearing their own challenges reflected in others is deeply affirming. One participant described how recognizing their own concerns in the experiences of peers boosted their confidence and helped them step more fully into their role. Knowing they were not carrying these questions alone made it easier to trust their judgment and remain open to learning. This kind of connection does not eliminate difficulty, but it changes how leaders relate to it.
There is a persistent assumption in leadership culture that support is something to be sought only when things are going wrong. In practice, peer connection is most powerful when it is woven into leadership before crisis hits. When leaders are connected at the top, they are better able to regulate their own reactions, sit with complexity, and make decisions that are both thoughtful and grounded. These outcomes are subtle, but they matter, not only for leaders themselves, but for the organizations and communities they serve.
Reframing peer support as a legitimate leadership practice requires letting go of the idea that strong leaders should be able to manage alone. Connection does not dilute authority; it strengthens it. Leaders who feel supported are often more reflective, more resilient, and better able to lead without becoming hardened or depleted by the role.
In a sector built on care and collective impact, it is worth asking why so many leaders feel they must carry the weight of leadership in isolation. Creating spaces where Executive Directors can be genuinely connected at the top is not an indulgence. It is a practical and humane response to the realities of nonprofit leadership today.
About the Author
Angela is a systems and professional development coach who works primarily with leaders and teams in the private sector, supporting high-responsibility roles to strengthen clarity, confidence, and effectiveness. Alongside this work, she has extensive experience coaching nonprofit Executive Directors and senior leaders navigating the demands of mission-driven organizations. Angela has also served as a board member and board chair for nonprofit organizations, giving her a grounded understanding of governance and the Executive Director–Board relationship. She is the host and facilitator of Executive Director Coaching Circles, peer-based spaces designed to reduce isolation at the top and support leaders through shared learning and deep listening. Angela brings a structured, thoughtful, and relational approach to her coaching and is particularly interested in the inner work of leadership and the role of connection in sustainable performance.
Connect with Angela on LinkedIn here.