Albert S. Cook Library at Towson University was charged with developing a new strategic plan under new library leadership and in the midst of remote work due to the COVID-19 pandemic. This article details Bryson (2018)’s Strategy Change Cycle as an approach for an academic library for conducting bottom-up strategic planning. Additionally, the project details department break-out activities that were used to help library employees stay engaged in an activity that had to be conducted remotely and in the midst of telework fatigue. This work is framed within the context of moving to a model of strategic management instead of one-and-done strategic planning as well as considering how to integrate a Critical Management Studies lens to make sure all feel included and empowered.