The current paper describes the conceptual foundation and practical application of an innovative framework for coaching business leaders. Build on the person-environment fit theory, the leader-organizational culture fit framework produces a set of conclusions regarding leader-organizational culture congruence and result in a number of unique approaches on coaching. The purpose of the conceptual structure is to create and expand the coach's personal insights concerning how the culture of an organization may provide for the leader's development of specific competencies, while potentially limiting the development of other capabilities. The proposed framework also has the ability to better support leader development approaches, in relation to coaching, with the wider development needs of the organization by identifying strategic ways through which the organizational leader can act as a critical agent for positive culture change. Furthermore, the paper discusses three methodological qualifications for the implementation of the proposed model: the application of parallel characteristics, corresponding measures, as well as evaluative assessments of characteristics. Finally, the paper discusses a number of important challenges and limitations towards implementing the proposed model within a coaching intervention.