This article shares wisdom from three leaders in the Baltimore nonprofit sector on university engagement with local communities. In conversation with the directors of Towson University's Grant Writing in Valued Environments (G.I.V.E.) program, the community leaders give practical advice to be used in grant writing and community engagement efforts, as well as interpersonal advice to guide interactions between universities and their community partners. When working with community partners toward their individual outreach goals, listening to their guidance and feedback is essential, as it provides structure and boundaries for universities to follow to prevent harm through their engagement. The article includes an introductory synopsis of G.I.V.E.'s work at Towson University, followed by reflections and discussions from Nancy Goldring, Arkia Wade, and David Fakunle, community leaders who work in Baltimore, Maryland. Each submission from community leaders is concluded with reflections written by Zosha Stuckey and Carrie Grant, in which they include their own thoughts regarding the input of the community partners' submissions.