The true impact of the Chicago Leadership Circle (CLC) lies in the business leaders who put its mission into motion. A joint initiative of Crain’s Chicago Business and the University of Chicago’s Graham School, the CLC is designed for executives who want to grow profitable, purpose-driven businesses while contributing to Chicago’s long-term economic and civic vitality. But what motivates leaders to take on this dual challenge and make a lasting difference?
To explore this question, we spoke with two of last year’s Fellows, Joli Robinson, CEO of Center on Halsted, and Carlos Vazquez, CEO of GoSprout, about the “why” that brought them to the fellowship and what they’ve learned from it.
What Inspires Our Fellows
For Joli Robinson, a recent Texas transplant to Chicago, the motivation to join CLC was clear: “The opportunity to dig deeper into various sectors and topics that impact Chicago was a huge draw for me. Getting the chance to join a cohort of invested peers and learning alongside and from one another, was just as important.” During her time in CLC, Joli focused on educating others about voter awareness and the complexities of Chicago politics.
Carlos Vazquez, CEO of GoSprout, whose organization has been exploring a deeper presence in Illinois, saw CLC as a powerful entry point. “I was looking for a crash course on Chicago, its politics, education, social justice, ethics, and history. CLC was the perfect combination of learning and building meaningful relationships.” Through the fellowship, Carlos forged meaningful connections, including a collaboration with Mark Potter from City Colleges of Chicago. Together, they presented a year-end project titled “Transforming Apprenticeship Success Through Visibility, Support, and Scale.”
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Learning Chicago: A New Perspective on the City
At the core of the fellowship is a deeper understanding of the city, its systems, its history, and its interconnected challenges.
“The experience has really helped me understand the ‘why’ behind what I’m seeing in Chicago today,” Joli shared. “That historical context has made me a more informed resident and contributor to our city’s future.”
Carlos echoed this sentiment, emphasizing how CLC has offered “a comprehensive way to gain insight” into Chicago, thanks in part to the caliber of the speakers and the structure of each session. “The intentionality behind every session has been phenomenal.”
Over the course of the fellowship, CLC Fellows expand their professional networks and deepen their leadership skills while exploring the key forces shaping Chicago’s economy. Through immersive sessions and discussions, they examine how business can help drive a prosperous future for the city. A hallmark of the program is its strong emphasis on cross-sector collaboration—bringing together leaders from diverse industries to work collectively toward meaningful change.
“It’s powerful to sit in a room with people from tech, post-secondary education, grassroots organizations, hospitality, real estate, you name it, and see how our work intersects,” said Carlos. “These diverse perspectives help us have deep, meaningful conversations about how to work together for the common good.”
For Joli, this breadth of viewpoints has been both grounding and inspiring. “I’ve been able to connect with rockstar peers that are all leaders in their own right & are just as passionate about supporting a thriving city.”
Capstone Projects: Turning Insight Into Action
The fellowship culminates in a capstone project. This opportunity allows Fellows to design an initiative that aligns their organization’s mission with Chicago’s broader economic and community development goals. For many, including Joli and Carlos, the capstone has been a defining and deeply rewarding part of the experience.
“The capstone is the culmination of everything we’ve been learning from the sessions and speakers to our collaboration with each other,” Carlos said. “It’s a real-world application of collective impact.”
The program is designed to equip Fellows with a deeper understanding of the economic and social forces shaping Chicago’s future. It gives them a clearer vision for creating shared value across their organizations and the region, meaningful relationships with socially responsible executives and civic leaders, and a roadmap for advancing institutional goals alongside the city’s progress.
For Joli, the fellowship offered something even more personal. Learning about Chicago’s history didn’t just provide context, it helped reshape her leadership approach. “It’s helped me understand the pitfalls that others may have made, and provided context when it came to neighborhoods and creating a strategic approach to the work I do. That historical grounding allows me to engage more meaningfully with community.”
The experience also left a lasting impression on Carlos, prompting a more introspective shift in how he approaches leadership. “This experience has pushed me to slow down and understand that meaningful change often takes time. I’ve learned to be more patient and to look for the right levers to move things forward.”
A Program That Leads With Purpose
What ties the Chicago Leadership Circle experience together is its intentional design, thoughtfully crafted to maximize both learning and connection. As J.M. Conway, Associate Director of Partnerships and Cohort-Based Learning at the Graham School, explains, “When you’re an advanced leader in your own field, you often spend most of your time with others in that same sector. Fellows frequently tell us how much they appreciate the chance to engage with people from other industries, hearing what they care about and recognizing shared challenges and passions from different perspectives. That cross-sector learning and collaboration is one of the program’s biggest strengths.”
This purposeful design is reflected in the program’s unique approach to exploring Chicago through multiple lenses. “We offer three lenses to view the city and its issues: the academic lens from UChicago scholars, the journalistic lens from Crain’s reporters, and the practitioner lens from business and political leaders,” Conway says. Each month, Fellows dive into a new topic, from Chicago’s history and politics to education, public safety, and civic leadership, ensuring a rich, multi-dimensional understanding of the city and its complexities. This intentional layering of perspectives helps leaders broaden their view, deepen their knowledge, and ultimately strengthen their impact across sectors.
By the end of the Chicago Leadership Circle, Fellows emerge with a sharper understanding of how business can be a catalyst for Chicago’s economic growth and social progress. They leave equipped with actionable strategies to address the city’s most pressing challenges while advancing their own organizations’ goals. Along the way, they build a powerful network of cross-sector peers committed to aligning profit-driven success with civic responsibility. This combination of insight, strategy, and connection enables Fellows to lead initiatives that strengthen their companies, create opportunity, and contribute to a more vibrant, resilient Chicago.
Explore the Chicago Leadership Circle
We encourage you to reflect on your own “why.” What about Chicago inspires you, and what impact do you want to create? The Chicago Leadership Circle is more than professional development, it’s a launchpad for informed, collaborative, and purpose-driven leadership. Discover more here.
