This paper describes the conceptual underpinning and application of a novel framework for coaching organizational leaders. Rooted in person–environment fit theory, the leader–culture fit framework yields a set of inferences about leader–culture fit and leads to several unique perspectives on coaching. The intent of the framework is to organize and augment the coach’s subjective insights about how the organizational culture may support the leader’s development of certain capabilities while potentially constraining the development of others. The proposed model also has the potential to better align leader-development strategies, vis-à-vis coaching, with the broader organization’s development needs by identifying key ways in which the leader can serve as an agent for positive culture change. From a methodological perspective, we discuss three requirements: the use of parallel attributes, commensurate measures, and evaluative judgments of attributes. We also briefly illustrate the model’s application using a case study that combines data from an organizational culture assessment with data from a parallel 360-degree leader assessment, and finally, discuss several key challenges and limitations to implementing the framework within a coaching engagement.