During COVID-19, academic library employees pivoted to predominantly remote work. Associate deans, associate university librarians, and equivalent managers at the top 50 Association of Research Libraries (ARL) institutions were interviewed about benefits, challenges, pre-pandemic norms, necessary conditions, and the future of flexible work arrangements (FWAs). The findings suggest that successful FWAs require adequate technology and effective managerial communication and depend on the types of positions and individuals involved. Most managers believe FWAs will increase in academic libraries in the future. FWAs provide benefits for both organizations and employees and will likely have a positive impact on library space, recruitment, and retention. At the same time, careful communication and compassionate leadership are needed for successful FWAs.