Online doctoral students from different cross-cultural generations may disconnect when dissertation chairs fail to understand how students' worldviews impact doctoral students during the dissertation-writing process. Because of the changing needs of digitally connected Generation Z students who will enter online doctoral programs by the mid-2020s, higher education leaders must create a model that will prepare online doctoral chairs to change how they mentor students and reflect on mentoring practices. The purpose of this qualitative exploratory case study was to examine how online dissertation chairs perceived the role of reflective mentoring practices and changing student cross-cultural and generational worldviews. The themes that emerged were online anonymity versus personalization, shepherd leadership versus transformational leadership, and meeting professional goals versus student-centered goals. The significance of the study is the need for online leaders to institute a change process that will be firmly in place for online dissertation chairs when Generation Z students are old enough to begin doctoral programs.