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The considerations that leaders of multihospital health systems must take into account in developing and implementing initiatives to build and maintain an exceptional pharmacy workforce are described.Significant changes that require constant individual and organizational learning are occurring throughout healthcare and within the profession of pharmacy. These considerations include understanding why it is important to have a succession plan and determining what types of education and training are important to support that plan. Other considerations include strategies for leveraging learners, dealing with a large geographic footprint, adjusting training opportunities to accommodate the ever-evolving demands on pharmacy staffs in terms of skill mix, and determining ways to either budget for or internally develop content for staff development. All of these methods are critically important to ensuring an optimized workforce. Especially for large health systems operating multiple sites across large distances, the use of technology-enabled solutions to provide effective delivery of programming to multiple sites is critical. Commonly used tools include live webinars, live “telepresence” programs, prerecorded programming that is available through an on-demand repository, and computer-based training modules. A learning management system is helpful to assign and document completion of educational requirements, especially those related to regulatory requirements (e.g., controlled substances management, sterile and nonsterile compounding, competency assessment).Creating and sustaining an environment where all pharmacy caregivers feel invested in and connected to ongoing learning is a powerful motivator for performance, engagement, and retention.