Many student affairs professionals have experienced grief spanning across their personal and professional lives. As student affairs professionals, they often serve on the "front lines" when bad things happen. These roles are mentally exhausting to take on and can be overwhelming. This article explores two different cases of staff deaths, from the perspective of the Senior Student Officer, at two unique institutions, and how the student affairs staff managed their own grief processes while leading and supporting their teams. A theoretical framework of secondary traumatic stress, grief, and healing is woven throughout the article, with special attention focused on the healing process and reflections for practice.