On March 18, 2025, Prosper Strategies hosted the webinar “Leading Your Nonprofit Through Change & Uncertainty.” The discussion centered on strategies for navigating financial uncertainty, diversifying revenue, and maintaining organizational stability in challenging times. We welcomed guest panelists, including:
- Sean Garrett, CEO of United Way of Metro Chicago. Since joining the organization in 2018, he has secured the largest corporate gift in its history, as well as $25 million from MacKenzie Scott. He has also focused on strengthening corporate funding partnerships while diversifying revenue streams for United Way of Metro Chicago.
- Stephanie Piccirilli, CEO of Ignite, a leading human services organization supporting youth experiencing homelessness. Under Stephanie’s leadership over the past five years, Ignite has increased revenue by nearly 70% and shifted from a reliance on government funding toward private and foundation support. Prior to Ignite, she co-founded Bright Endeavors, a social enterprise in Chicago that later merged with New Moms.
- Dorri McWhorter, who recently stepped away from her role as CEO of YMCA of Metro Chicago. During her three years at the organization, she nearly doubled revenue and significantly reduced its deficit. Before her time at the YMCA, she led YWCA Metropolitan Chicago and played a key role in expanding its impact.
During the webinar, each panelist shared insights on diversifying revenue in response to potential federal funding threats, scenario planning, and strategies for maintaining morale within their organizations.
Current Funding Environment Challenges
One of the biggest challenges nonprofits face today is financial uncertainty. Panelists shared their perspectives on the importance of funding diversification.
Dorri put it best when she said, “I always say there’s not one good or bad source of funding that we need—I need all the monies from all the sources because the fact of the matter is… no source is guaranteed. I don’t care what the source is. None of it is ever guaranteed.”
Stephanie shared that one of Ignite’s strategies has been to diversify revenue by program so that if funding is eliminated, programs with multiple revenue sources can still survive. “We moved away from a model where…one grant funds an entire program. And we’ve kind of spread the funding across all of the work that we do so that if we do lose a funding source, it doesn’t put one program or service we offer at risk.”
Sean emphasized that diversification should be part of a broader growth strategy rather than an end goal. “Diversification in and of itself is not necessarily the goal. It’s a way to be protected towards other goals, and it’s an important strategy. But it should be part of a growth strategy.”
All the panelists agreed that while there is no perfect funding formula, understanding your nonprofit’s business model and recognizing all available funding sources—including government, private philanthropy and consumer funding—is crucial.
Organizational Response Strategies
Panelists also shared key strategies for navigating uncertainty:
Maintain a Calm, Strategic Approach
“Our job is to stay stable. Our job is to stay strong. Our job is to…be compassionate, but also calm in these settings so that we are clear headed and clear eyed enough to make the right decisions while still pursuing the work that we’re trying to do,” noted Sean.
Review Language and Policies
The question arose about whether organizations were adjusting their language due to evolving federal guidelines. Panelists discussed taking a multi-lens approach—considering legal implications, risks, and strategic choices—while staying true to core values. Stephanie noted that some new federal contracts include specific language and rules that organizations must adhere to. The overall emphasis was on being strategic and thoughtful about language choices in the current environment.
Strengthen Board Engagement
Sean highlighted the importance of board engagement, stating that he has been transparent with his board about the challenges ahead and the need for their help. He emphasized the need for board members to focus on offense, not just risk mitigation, and to help amplify efforts and bring new people to the table.
Dorri also stressed that board members can’t sit on the sidelines—they must actively engage in addressing mission-related challenges, especially during uncertain times.
Team Management & Communication
Panelists underscored the need to create a sense of stability internally. “I have to create this space for our staff to do the work that they need to do and not be distracted by everything that’s happening and that I’m shifting…kind of creating this bubble around our team and our young people so that they can do the things that they need to do,” said Stephanie.
Some of the key recommendations for nonprofit leaders included:
- Maintaining open-door policies
- Being honest when answers aren’t known
- Communicating commitment to organizational values
- Creating space for difficult conversations
Stephanie concluded by sharing, “Trust to me is the foundation of all of this. You can’t manage change effectively. You can’t lead an organization through difficult times, and you can’t lead an organization through great times too externally unless there’s that trust there.”
Recommendations for Moving Forward
As nonprofits navigate ongoing challenges, panelists shared key takeaways for not just surviving, but thriving:
- Bringing diverse voices into decision-making
- Building organizational agility
- Focusing on mission delivery regardless of funding source
- Maintaining advocacy efforts
- Creating stronger ecosystem partnerships
- Remembering that change and uncertainty are constants
By adopting these strategies, nonprofits can remain resilient and mission-driven in the face of uncertainty. You can watch the entire webinar discussion, here.
