In Session is a video series from the Aspen Institute featuring conversations with leaders across its network as they reflect on their personal leadership journeys and share practical insights grounded in their experiences. In the latest episode of In Session, Co-Executive Director of Aspen CSG, Chris Estes talks about centering leadership on mutual benefit, collaboration, and creating intentional spaces for trust and shared learning.
Below is a transcript of the video:
“I think the key element of leadership that I’ve always centered on is finding the mutual benefit. Whether you’re leading an organization and a staff and trying to set a tone that people feel like, “I’m in this and I have an opportunity to grow, develop, or have an impact,” that sense of shared benefit is really key to building a successful organization and team. In the same way, when you’re trying to help communities move forward and improve outcomes, place becomes that shared benefit, that mutual shared benefit.
I’m Chris Estes, co-executive director of the Community Strategies Group, and here are a couple of things I wanted to share about leadership. One of the most important lessons I’ve learned and tried to practice as a leader is avoiding the zero-sum framework—the idea that there is one winner, or if I win someone else loses. That applies both internally as an organizational leader with staff and externally as an organization working with other organizations or communities.
The importance of this is that we never have all the resources we need to do the work we want to do. Whether organizationally, as a community, or across a field, if we’re not maximizing the talents of everybody involved, we’re never going to be as successful. This requires shifting the paradigm away from a scarcity or deficit framework to one that says, “We’re all better off if we can collaborate and maximize.” It takes people working together and recognizing that shared relationships lead to mutual benefit. That, in turn, draws more collective attention to our work and increases collective impact on outcomes.
This collaborative approach also sets a tone that leads to greater buy-in and typically attracts more investment from funders. Funders are often excited to see a synergy of efforts coming together, rather than people being pitted against each other for a single grant or a single piece of credit. So again, avoiding that zero-sum outcome and really centering collaboration, trust-building, and mutual benefit is, in my experience, absolutely key to success.
The second leadership element, both internally and externally, is how to intentionally structure environments that build trust and foster learning. It’s one thing to say “we’re all working together” or “we all matter,” but it requires structure to make sure colleagues and community members can truly learn from one another. That takes real intentionality. How do we create not just a safe space, but a structured space that results in mutual learning?
In practice, this looks like structuring conversations where people share something they’re working on, struggling with, or a question they have, and the rest of the group can only ask questions for the next 15 minutes. No advice, and no advice disguised as a question. This centers the process on learning more about that person’s situation, their organization’s work, or the task at hand. Over 10–15 minutes, people are forced to listen, learn, and engage deeply—not just wait for their turn to make a point. That’s where real peer learning happens.
One of the key elements of being a leader is fine-tuning and asking the right question. And when I say fine-tune, I mean it literally. It’s about getting to a what will it take question that is sharp and focused—not something cosmic like “what will it take to get to world peace,” but rather, “what will it take for this specific change to happen?” Then, you facilitate a process that guides people through their current understanding, pushes them to think and imagine new possibilities, and ends with collective learning and concrete recommendations.
This approach is both an effective communication strategy and, to me, a core act of leadership. It means centering on the right question, listening carefully, and designing discussions that move people forward in a structured way—rather than asking people to brainstorm loosely, which often doesn’t feel safe or yield the best thinking.”
