The evaluation of leadership in health services necessitates a nuanced and contextually sensitive approach. This chapter explores the complexities of evaluating leadership, emphasizing the importance of aligning evaluation strategies with the specific roles and responsibilities of leaders. It highlights the limitations of one-size-fits-all approaches by examining two contrasting contexts: the “caught in the middle” phenomenon of hospital middle managers and the collective leadership of general practitioners engaged in community work. The chapter provides practical guidance for practitioners, offering frameworks and guiding questions to facilitate the design and implementation of effective leadership evaluations tailored to the unique challenges and opportunities presented in different health service settings.