The Smart Museum of Art at the University of Chicago recently recast an existing personnel structure (docent program) into a platform for both campus and civic engagement. This initiative brings together University students and alumni of the South Side Odyssey Project program as paid educators. The Odyssey Project is a free, 36-week, college-credit granting humanities program for incomeeligible adults with limited to no access to higher education. This presentation examines ways of cultivating power within community stakeholders, challenges and successes of convening different publics to support these efforts, and ways to embed meaningful engagement efforts into sustained institutional practice.