Over the past few months, I had the opportunity to contribute to two very different publications.
One explored interim leadership and nonprofit transitions for Nonprofit Quarterly: “Capacity Is Tested in Transition: Interim Leadership as Nonprofit Infrastructure.” The other contributed to JD Dillon’s new book, The Frontline Enablement Playbook, which focuses on supporting “deskless workers.” Think food bank workers, youth program staff, community health workers, and farmers market managers, among many others.
On the surface, these topics don’t seem connected. One focuses on executive leadership. The other focuses on frontline workers. One examines what happens when a leader leaves. The other examines what happens every day when people show up to do the work.
What interim leaders and frontline workers do share is that they occupy critical boundary positions.
Interim leaders stand between an organization’s past and future. Frontline workers stand between an organization’s mission and the community it serves. Both operate in environments filled with uncertainty, competing demands, and imperfect information. Both rely heavily on judgment. Both see things that people elsewhere in the organization often miss. And both groups have important lessons to teach us about how organizations learn, adapt, and move their missions forward.
The people at the center
For a report on interim leadership commissioned by Third Sector Company and the subsequent Nonprofit Quarterly article, I spent time immersed in research and conversations about nonprofit leadership transitions.
One finding stood out. Leadership transitions are often treated as temporary disruptions—something organizations simply need to survive. But transitions are actually moments when an organization’s strengths and weaknesses become visible. Governance, culture, communication, decision-making, and trust all come into focus. As I wrote in the article, transition is not neutral. It either weakens an organization or strengthens it. The stakes of getting it right have never been higher.
The interim leaders I learned from weren’t simply keeping the lights on. They were helping organizations stabilize, learn, prepare, and move forward. They were building capacity in real time.
What struck me most was that transition acts like a stress test. It reveals what is strong, what is fragile, and what has been ignored. The best interim leaders don’t just help organizations survive that moment. They help organizations learn from it.
We invest significant resources in other aspects of capacity building: training, strategic planning, and leadership development. Yet leadership transitions may be one of the most powerful—and underutilized—opportunities for organizational learning. A leadership transition is not simply about finding the next executive director. It is an opportunity to build a stronger organization for everyone who depends on it.
The people in the field
Also in May, JD Dillon’s book about how to strengthen our “deskless workforce” came out. I contributed examples from food banks, farmers markets, and international development organizations serving rural communities. These organizations rely on staff and volunteers who are often juggling multiple responsibilities with limited time, training, and resources.
The lesson isn’t that these workers need more information. The lesson is that they need the right support at the right moment. Here are some examples:
- In food banks, volunteers perform physically demanding tasks in fast-moving environments. They don’t have time for training, so we developed flip cards placed at volunteer stations to put learning where it was most needed.
- In farmers markets, managers repeatedly answer the same questions about SNAP accounting and requirements. An orientation in May isn’t helpful for farmers selling in August. We made information available in the flow of work through tools such as QR codes and mobile resources.
- In rural international development healthcare work, staff faced situations that required sound judgment related to safeguarding and human trafficking. Rather than focusing solely on information, we created opportunities to practice decision-making when the stakes were high.
Across all three examples, the most effective solutions weren’t complicated. They were practical, timely, and grounded in the reality of how people actually work.
A common lesson
These projects pulled me toward opposite ends of the organizational chart, yet both pointed to the same conclusion.
Our missions depend on high-performing people working within high-performing organizations operating in complex environments. Few people have visibility across all three.
Positioned at critical boundaries, interim leaders and frontline workers can help organizations make sense of what is happening around them. Interim leaders stand between an organization’s past and future. Frontline workers stand between an organization’s mission and the community it serves. Both see realities that others may miss.
We can design solutions that span the continuum from individual to organization to systems—from flip cards at a food bank volunteer station to sector-wide efforts that strengthen governance, leadership transitions, and organizational effectiveness. The scale may differ, but the underlying work is remarkably similar.
In every case, we begin by listening to the people who occupy these boundary spaces. They often see emerging challenges, hidden opportunities, and practical realities before anyone else. Their experiences offer valuable insight into how people, organizations, and environments interact—and where change is most needed.
Perhaps that is what makes these roles so valuable. The people filling them don’t just do important work. They help organizations understand themselves and make sense of the world around them.
Gratitude: I write this with tremendous gratitude for the frontline workers who make our world move forward, and to Third Sector Company for inviting me to spend time with so many inspiring interim leaders.
——–
Read more:
- “Capacity Is Tested in Transition: Interim Leadership as Nonprofit Infrastructure” (Nonprofit Quarterly) – https://nonprofitquarterly.org/capacity-is-tested-in-transition-interim-leadership-as-nonprofit-infrastructure/
- The Frontline Enablement Playbook by JD Dillon – https://jddillon.com/frontlinebook/
- Interim Leadership in the Nonprofit Sector 2025 Report – https://interimexecutivesacademy.com/interim-leadership-in-the-nonprofit-sector-2025-report/