Ximena was sure she would be appointed as the Director of Student Life at Aspirante University, a Hispanic-Serving Institution. As interim director, Ximena strove to enact servingness in her everyday practice. Her efforts to create a culturally responsive, relevant, and affirming campus environment for Latinx students were unparalleled. However, she was overlooked yet again for the directorship. This case study is intended to challenge leaders to check their assumptions and examine how they operationalize Whiteness, reproduce the dominant model of professional, and thereby preclude candidates from being earnestly and equitably considered for the job. It raises implications for current leaders who may enact deficit thinking and racially and culturally biased practices as well as for leaders who may be hindered by such practices.