This chapter explores the efficacy of virtual cohorts and how they may positively affect both leadership skills and wellness for emerging and current leaders. The authors initially met at Harvard University's Leadership Institute for Academic Librarians (LIAL) program in 2018 and then continued to meet virtually on a regular basis for the following four years. Cohort meetings emphasized practicing the skill sets taught at LIAL. This included both case study writing and Lee Bolman and Terrence Deal's “four frames” model. The authors self-administered surveys to assess the impact of participating in the cohort on a number of criteria including perceived value of the cohort, impact on the skill sets prioritized by the cohort, perceived wellness benefit during the trials of COVID-19, and cohort influence and/or impact on career progression. The chapter also includes recommendations for the development of future cohorts including best practices for scheduling, membership, and cohort focus.