Thrown Into the Deep End: Leadership, Capacity, and Collaboration

Nonprofit leaders across sectors are navigating a period of heightened uncertainty. Funding streams are shifting or disappearing, leadership transitions are accelerating, and long-standing operational challenges are being brought to the surface under pressure. At the same time, many leaders are being asked to adapt quickly: often without the frameworks, experience, or capacity they would normally rely on.

In this conversation, Collectivity Managing Partner Scott D. Cole and Business Development Lead Ben Litwin reflect on what they are seeing consistently across organizations: how financial strain amplifies existing issues, how isolation has shaped leadership culture, and why collaboration and systems-level thinking are becoming increasingly critical.

Disclaimer: This interview was recorded and edited with the assistance of ChatGPT and is presented as a good-faith representation of the speakers’ intent. It is not a verbatim transcript.

Across leadership and the many types of organizations you work with, what operational pain points are you seeing consistently? Are similar challenges showing up regardless of organization or leader type?

Scott D. Cole: Operational challenges tend to surface more readily during periods of instability, especially when funding becomes uncertain. Over the first half of the year, the termination of many grant dollars created widespread implications across city, county, state, and federal funding streams. As those dollars flowed, or stopped flowing, organizations were forced to scramble to fill funding gaps. This pressure exposed existing operational weaknesses, particularly where organizations had relied on specific funding sources to support certain programs. Leaders were then forced to quickly adapt their operations without knowing whether those programs could continue to be funded.

Ben Litwin: These challenges are especially amplified in organizations with smaller teams, where individuals carry significant institutional knowledge. When stress increases and capacity is stretched, those structural vulnerabilities become much more visible. Existing issues are not new, but they are intensified by uncertainty and added workload.

So a unifying theme across organizations is whatever challenges already exist tend to become amplified by funding challenges, making them harder to ignore or manage.

Scott D. Cole: Exactly. Leadership transitions further complicate this moment. Many new leaders are stepping into roles without having prior experience navigating crises of this magnitude. They are being asked to respond to complex, high-stakes situations before they have fully developed the leadership skills or hands-on experience needed. As a result, they often lean heavily on their teams while trying to learn in real time how to manage catastrophic or rapidly changing conditions.

Ben Litwin: This lack of preparation highlights the absence of clear frameworks for scenario planning. Many leaders do not have structured ways to decide what programs to protect, what to pause, or what to temporarily step away from, which makes decision-making under pressure even more difficult.

In a time of funding cuts and shifting expectations, what new skills are nonprofit leaders being forced to develop quickly? Are there skills leaders are being pushed to adopt whether they want to or not?

Scott D. Cole: Collaboration and collective action have long been important, but they are now essential. Leaders are increasingly leaning on one another by finding spaces, time, and forums to share knowledge and experience. Across the sector, there is a noticeable increase in workshops, seminars, and conversations focused on collaboration. Social media discussions among leaders also consistently emphasize the importance of working together. From a personal perspective, leaders are actively seeking support systems that reduce isolation. These support systems can take many forms, such as culturally specific communities, organizational affiliations, or peer networks. At its core, this shift is about moving out of isolation and into shared spaces where leaders can think and problem-solve together instead of working alone behind closed doors.

Ben Litwin: The isolation factor is significant. During the pandemic, leaders learned how to function in highly isolated environments. While that allowed work to continue, it also created habits that are now difficult to break. As leaders re-enter more connected, public-facing work, they are having to relearn how to engage collectively, even though isolation still feels familiar.

Scott D. Cole: This shift feels cyclical, like a pendulum. Post-pandemic, many leaders are still reorienting themselves after years of isolation. While reconnecting has been freeing, it is also unfamiliar and uncomfortable for people who became accustomed to working alone. The current political and administrative environment has made it clear that connection and visibility are necessary, but rebuilding those habits takes time and intention.

Ben Litwin: Choosing to “ride things out” alone is not a viable strategy in this environment. Supporting others, bringing people along, and engaging collectively is better for the overall ecosystem and for leaders as humans. Systems survive best when people act together rather than retreating into individual silos.

Given challenges around funding, isolation, and collaboration, what types of support and services are most critical for leaders right now? Where do organizations benefit most from a systems-level partner or approach?

Scott D. Cole: Many leaders instinctively understand that systems-level work is important, but they lack experience actually doing it. Because most nonprofits are under-resourced, leaders are often focused on daily survival tasks rather than collaborative or long-term systems work. As a result, they have not exercised the muscle required for sustained collaboration. It often takes a major external disruption, such as a new administrative environment, to push organizations out of their operational cocoon. When that happens, leaders may feel unprepared. This is where systems-level partners are critical, as they provide expertise, structure, and guidance for collaborative work that organizations do not have the capacity to develop on their own.

Ben Litwin: Systems-level change only happens when people are willing to come to the table, see the bigger picture, and step away (briefly) from day-to-day tasks to think collectively.

Scott D. Cole: Our approach views organizations as organisms within a larger ecosystem. Just as in nature, everything is connected. Individual organizations function like cells or organs within a broader system. Even if an organization does not directly engage in systems-level work, it still benefits from improvements across the ecosystem that affect how services are delivered. No single organization can solve large-scale systemic issues alone. For example, challenges in child care or food systems involve hundreds of organizations and multiple layers of government funding. These problems require coalitions and shared infrastructure to address distribution, policy, and sustainability at scale.

Ben Litwin: Healthy systems require alignment at every level, from internal organizational systems to large-scale networks. When those pieces work together, the entire ecosystem becomes more resilient and effective.

Is there anything else you would like to share?

Scott D. Cole: Our organization maintains an open, ongoing invitation for leaders and organizations to engage in conversations about collaborative work. Wherever a leader feels challenged, across a wide range of possibilities, we are prepared to support them and help them navigate what comes next.