Within this study, the researcher explored the effect that supervisors have on the availability and flexibility of bereavement leave for employees who have experienced the death of a loved one. A qualitative phenomenological approach was applied in Zoom interviews of 23 participants who provided detailed feedback on their overall experience of managing personal and professional responsibilities during bereavement based on the ways that formal and informal policies were applied. Barclay and Kang’s bereavement at work model guided a series of semi-structured interviews, and questions were based upon Bauer’s questionnaire about grief in the workplace. A high number of participants (20/23) noted that their relationship with their supervisor either positively or negatively affected their experience with workplace bereavement policies. Four overall themes were noted: general importance of relationship with supervisor, supervisor flexibility in awarding leave, employee perception of organizational justice, and supervisor control of information.