This study examined the supervisory interactions of past and present residence life staff members, specifically, the implications of race on the residence life professional (HD)/residence life student staff member (RA) supervisory relationship. College and university residence halls provide some of the most diverse environments that individuals will encounter as they move through life (Amada, 1994; Jaeger & Caison, 2005). It is in these spaces that individuals learn the most about themselves and others. Thus, learning to navigate multicultural interactions is critical. Facilitated by residence life staff, this knowledge serves as preparation for the actual experiences and situations students will face once they are in the "real world." Although some areas of the higher education literature were limited, the literature review supported the role that residence life staff members have in preparing student staff members (whom are also residents) for the workplace. Learning how to handle situations in the workplace where there are differences such as language, race/ethnicity, culture, or values and beliefs will aid in positive interactions with others and ultimately contribute to a better working environment--inside and outside of the residence halls. Qualitative methods were used for this study because of their attention to vivid and layered descriptions. These descriptions give voice to a person's experiences and interactions and help them make meaning of their own worlds. As a result of residence life staff members living where they work, the most appropriate way to further examine their life experiences was through a phenomenological lens. In addition to the aforementioned qualitative methods, modified versions of quantitative instruments from an earlier study (Ladany, Brittan-Powell, & Pannu, 1997) and two other scales (Helms & Carter; 1990; Helms & Parham, 1996) were used to measure the racial identity development of the participants. These inventories relied on participants to self-report their perceptions. After these assessments were completed, interviews were conducted with 10 randomly selected participants (five RAs and five HDs). Five themes emerged from these participant interviews: prestige, protection, privilege, proximity, and preparedness.