Senior Student Affairs Officers (SSAOs), whose primary responsibility is the health, safety, and well-being of students, were at the forefront of leading their campuses through the COVID-19 crisis. In Fall 2020 a diverse group of 23 SSAOs was interviewed to understand the contexts and issues that influenced decision-making during the pandemic. A focus on students, alignment with institutional contexts, and financial realities were consistently identified as key influencers of decision-making. Effective decision-making often entails a balancing act of several factors. The implications of this study can be used to inform student affairs practice and the professional development of graduate students and future and current SSAOs.