Effective role adjustment is crucial for the successful transition of chairs from faculty to academic leaders. Drawing on the data from semi-structured interviews with a select group of Filipino department chairs, this qualitative grounded theory inquiry applies Weick's framework of sensemaking to the analysis of their role adjustment process. The study attempted to provide a model, which would ensure that newly appointed chairs have a proactive experience of being holistically involved in their role adjustment process. Implications are drawn for incumbent chairs, those who currently serve as chairs, faculty who are considering the chairship role, deans, and administrators who are assisting new chairs adjust to their role.