The purpose of this qualitative multi-case research study was to explore how senior administrators at four higher education institutions learned and made decisions during the first two years of the COVID-19 pandemic. Bandura’s social cognitive theory guided this study as it addressed how people learn enactively and vicariously as well as the triadic reciprocal causation between environmental, personal, and behavioral factors. The study included 13 senior administrators and data were collected through semi-structured interviews. The data analysis followed Creswell and Guetterman’s six-step process for analyzing and interpreting qualitative data. Data analysis involved both inductive and deductive coding and categorizing codes into sub-themes and themes. Trustworthiness was ensured through researcher reflexivity, peer debriefing, member checking, and thick description. All participants engaged in some form of observational learning, predominantly from within their own institution or across the university system. Perceived self-efficacy had a significant influence on leadership learning and decision-making. Participants shared their values of teamwork and collaboration and consistent communication in service to keeping their communities safe and continuing their institutional educational missions. The results of this study demonstrated the importance of observational learning on how leaders learned during the COVID-19 crisis, as well as the importance of self-efficacy including coping efficacy and its influence on a leader’s confidence, flexibility, and resolution during times of significant and rapid change. Practical implications include recommendations for crisis management planning, teambuilding, and communications strategies to improve academic leadership self-efficacy.