This study aims to analyze if work flexibility mediates the relationships between technology leadership, digital skills, organizational culture, and digital adaptation of administrative staff in private Higher Education Institutions City of Bandung, Indonesia. This research is targeting 138 private higher education institutions. Of 1325 eligible administrative staff to be surveyed, 203 gave their response to the questionnaire. PLS-SEM was used to analyze the data collected. The findings suggest that technology leadership, digital skills, and organizational culture significantly affect the digital adaptation of administrative staff. Work flexibility mediates the impact of the three independent variables on digital adaptation. This research, however, has several limitations including sample limitation and baseline on the context of the private higher education institutions in Bandung’s city. Recommendations would be to improve training a technology leader and digital skills and strengthen an organizational culture that supports innovative culture and work flexibility. Further research should broaden the scope of the sample and other factors in the context.