Increases in the technological availability of the digital workplace and shifting expectations after the COVID-19 quarantines in 2020-2021 have caused a significant increase in institutional capacity, and employee expectation of flexible work options in higher education. An analysis of institutional practices and experiences of higher education employees is needed to build a scant body of research on the topic and guide higher education leadership as they engage in policy development. By better understanding what workers in higher education value, leadership can more accurately assess and improve crucial organizational practices and policy through work flexibility such as recruitment, retention, and employee satisfaction. In this study, interviews with academic advisors representing 16 different Association of American Universities (AAU) institutions were conducted to better understand how employees define work flexibility, its meaning to them as employees, and how it impacts them as individuals. Our study revealed four primary themes centered on how higher education employees want the ability to customize their role, be treated with compassion, feel trusted in the workplace, and have clarity around work flexibility expectations.