Community engagement professionals (CEPs) often must develop and maintain equitable, high-quality relationships with community partners while supporting student learning and civic development through cocurricular community engagement or for-credit community-based learning programs. Lack of alignment between campus goals and values and those of communities creates challenges for CEPs. Our community partners have expressed the feeling that students were not adequately prepared for community engagement and that it is the university’s job to prepare them. To support partnerships in inclusive and equitable ways, CEPs need to be skilled and comfortable with some critical, complex topics before they can train students or provide professional development to instructors. This reflective essay examines specific strategies for CEPs doing this work, informed by the literature, feedback from community partners and social justice training professionals, and classroom experience. Topics addressed include social identity, systems of privilege and oppression, cultural humility, and institutional–community power dynamics.