Inside CSS’s Listening Tour with Nonprofit Leaders

Inside Civic Safeguard Strategies (CSS’) Listening Tour with Nonprofit Leaders 

By Clara Meekins (University College Maastricht)

“No one had asked me how I was doing.” 

At a moment of sustained pressure and growing uncertainty for nonprofits across the United States, Civic Safeguard Strategies (CSS) recognized the importance of first understanding what leaders were experiencing. Rather than beginning with assumptions about what organizations needed, CSS began by listening. 

I spoke with CSS founder Eileen Lawless about what inspired this listening journey, what the process looks like, and what the experience has been like so far. 

What prompted CSS to undertake this listening tour? 

Following years of work supporting organizations overseas by helping to strengthen civic space, or the environment in which people participate in society, in complex environments, CSS’s founders have turned their focus to the domestic nonprofit sector. As civic space increasingly comes under threat here at home, Eileen and her co-founders are drawing on their comparative experience abroad to better understand and serve nonprofit leaders in the United States. 

Eileen’s experience leading listening initiatives abroad in places like Syria and Libya reinforced the value of conversation as a way to understand people’s lived experiences. She has carried this into her work with CSS through this listening tour, which creates an environment for genuine human connection. 

“The best way to really understand what your work means or could mean to other people is to talk to them about it,” Eileen explains.

So, what exactly is a listening tour? 

At its core, a listening tour is about creating space for conversation. This approach sets aside expectations and the idea of ‘right’ answers. Instead, participants are encouraged to reflect openly on their experiences, challenges, and perspectives. Most conversations in this tour  involve just two people, Eileen and a non-profit leader, and last about an hour, though they’re flexible. Eileen brings a set of guiding prompts but rarely asks every question in every conversation.

“If someone wants to go in a direction adjacent to the prompt, that’s often where the most interesting insights come from.” Eileen observes. These conversations don’t focus on collecting data. They are about understanding lived experience. It is important to Eileen that the listening tour is not extractive like many other forms of research can feel. She plans to share the synthesis of what she learns back to every single participant, as well as the wider community of practice. 

Why did you take this approach rather than a standard survey or report?

“We wanted the opportunity to connect with the people whose experiences we’re hoping to support,” Eileen says. “And this tour is an incredible tool to do that.” 

Unlike a survey, the listening tour isn’t bound by a script. The conversations evolve naturally through follow-up questions and tangents, allowing each nonprofit leader to focus on the issues that feel most important to their organization and their experience. 

It’s also a practical approach. Rather than requiring extensive funding or formal research methods, a listening tour simply requires time, curiosity, and a willingness to listen. It also requires the generosity of participants in giving their time to the effort, for which Eileen is grateful. 

How have participants reacted to being listened to in this way?

This listening tour has largely been met with curiosity, which often gives way to connection, and, as some participants have described it, “cathartic.” In this way, the tour has gone beyond just gathering insight to providing space for leaders navigating a complex landscape and carrying enormous responsibility. 

While Eileen initially planned for each conversation to last about 30 minutes, she quickly realized participants were eager to share more than could fit into that time. Now, conversations last about an hour, giving leaders the space to reflect on and share their experiences, and truly be heard. 

“It seems that no one has really asked them how they’re doing,” Eileen noticed through these conversations. “People ask how their organization is fairing at this moment, but not how they themselves are experiencing this moment specifically. A word that surfaces pretty often is, “isolated.” Leaders are bearing a lot and it can feel lonely.”

At its heart, the listening tour is about creating this necessary space to pause, reflect, and be seen and heard.

When you started the listening tour, what was your hope for these conversations?

When Eileen began the listening tour, the goal was straightforward: to better understand how leaders in the U.S. nonprofit sector were experiencing this moment of sustained pressure and uncertainty. Yet, as the conversations have continued, the tour has begun to serve another important purpose, one she didn’t anticipate. 

In the midst of a challenging period for the broader civic space, this listening tour has become an unexpected source of perspective and renewal. Eileen describes starting CSS following the dismantling of USAID, a moment she remembers as deeply painful and far from hopeful. These conversations have offered a different view: a reminder that thoughtful, passionate, smart, hardworking, and courageous people are continuing to show up every day to dedicate their lives to something larger than themselves. 

“In a moment when our social fabric can feel tattered, talking to these leaders gives me hope. It gives me the energy to keep digging in.” 

The hope is that the listening tour culminates in a unifying moment of live-sharing the synthesis of the effort which itself creates connection among the nonprofit leaders who participated: “I hope to gather everyone together to hear the common themes, shared experiences, and challenges as well as wins that I heard across the conversations. Ideally, this inspires leaders to connect more with each other, seek support from each other, laugh about the absurdity of the things they deal with, and, through that, to know they are not alone,” Eileen says. 

Join the Conversation

CSS hopes to conduct 100 conversations across all 50 states, and the team is still looking for nonprofit leaders willing to participate.

If you work with or lead a nonprofit, whether it’s large or small, volunteer-run or have paid staff, a registered 501(c)(3) or an organization supporting one, you are invited to join the conversation.

Email eileenl@civicsafeguardstrategies.com to connect with Eileen and set up a call. 

This is an opportunity to share your experience, reflect on this moment, connect with others doing mission based work in all 50 states, and shape how organizations like CSS can better serve the nonprofit sector.