As the number of racially diverse students on university campuses in Canada increases, so too do questions about whether and how postsecondary institutions are equipped to create a welcoming, respectful, and supportive learning community for a racially diverse student body. This research explored how a residence life management (RLM) team could build capacity to meaningfully engage with the subjects of race and privilege in an effort to contribute to the university's purpose of advancing a just society. Guided by collaborative developmental action inquiry and participatory action research, this project engaged members of the RLM team to consider how they are currently navigating the subject of race and privilege and to identify support required to better facilitate learning on the subject of race and privilege. It also provided the RLM team an opportunity to transform a tangible leadership challenge into an organizational learning opportunity. Study participants indicated that engagement with the subject of race and privilege is currently limited and suggested that capacity building could be enhanced in two key ways: first, through an explicit organization-wide commitment that informs hiring and employee performance management metrics, and second, through intentionally designed spaces for learning and action through dialogue. This study identifies practical strategies to engage with the subjects on race and privilege and contributes to current literature on race and privilege by identifying both barriers and factors that enable engagement with the complex and necessary dialogue about race and privilege in a Canadian university context.