Moving Beyond the Surface.
Each Real Talk session will bring you a meaningful conversation with other Chicago leaders.
-
Let's Get Awkward (Then Get Aligned)
Not everything that counts can be counted. In this session, we’ll surface the disconnects and assumptions that strain cross-sector relationships, including how impact is measured, who gets to define it, and how funding priorities are set. Together, we’ll identify the gaps between myth and reality—and push past them to imagine a more collaborative, inclusive approach to community impact.
Wednesday, January 21, 2026
4:00 p.m. - 6:00 p.m.
Malcolm X College
Learn more about panelists below!
-
The Funder-Nonprofit Situationship
Let’s be real: great partnerships don’t happen through emails and RFPs alone. This session gets to the heart of how trust, respect, and clear roles fuel real progress. We’ll talk about what it looks like to honor the expertise of community-based organizations, navigate power dynamics thoughtfully, bridge the gap between CBO-speak and corporate-speak, and show up as true partners.
Tuesday, March 17, 2026
4:00 p.m. - 6:00 p.m.
Malcolm X College
Learn more about panelists below!
-
It's Not You, It's the System
In this session, we’ll dig into how entrenched funding practices create barriers for community-based nonprofits and explore what it looks like when leaders across sectors actively disrupt those patterns. We will explore innovative Chicago-grown models that change who has power, who has access, and how resources move. Come ready to interrogate the status quo, challenge your own defaults, and imagine partnerships that don’t just patch the system—but rebuild it entirely.
Wednesday, May 6, 2026
4:00 p.m. - 6:00 p.m.
Malcolm X College
Stay tuned for announcements on our dynamic panelists for this session.
Let’s be real: great partnerships don’t happen through emails and RFPs alone. This session gets to the heart of how trust, respect, and clear roles fuel real progress. We’ll talk about what it looks like to honor the expertise of community-based organizations, navigate power dynamics thoughtfully, bridge the gap between CBO-speak and corporate-speak, and show up as true partners.
Moderator Shelley Davis (President & CEO, South Shore Synergy) will be joined by panelists Malcolm Crawford (Founder & Director, Austin African American Business Networking Association Inc.), Aaron Dannenbring (Philanthropist & Startup Founder/Advisor), Michelle Rashad, (Executive Director, Imagine Englewood If), and Monali Shah (CEO, Inflowio).
Session 2: The Funder-Nonprofit Situationship
Session 1: Let’s Get Awkward (Then Get Aligned)
Not everything that counts can be counted. In this session, we’ll surface the disconnects and assumptions that strain cross-sector relationships, including how impact is measured, who gets to define it, and how funding priorities are set. Together, we’ll identify the gaps between myth and reality—and push past them to imagine a more collaborative, inclusive approach to community impact.
Moderator Shelley Davis (President & CEO, South Shore Synergy) will be joined by panelists Nancy Bonges (Director of Community Engagement, William Blair), Manny Rodriguez (Co-founder and Executive Director, Revolution Workshop), Steven Shaw, (Community Engagement Director, Verizon), and DeAnna Sherman (Co-Founder and Executive Director, True Star Media).
