This paper examines (1) the definition and concept of leadership as reflected in educational institutions and formal organizations, (2) patterns and models of leadership in the western India context, (3) the resultant functionality and dysfunctionality contributing to the health and pathology of systems and (4) leaderships models and qualities relevant for todays times. Western patterns of leadership are examined in the feudalistic, paternalistic, democratic and bureaucratic. The leadership behaviour is categorized as supportive, directive, achievement oriented and participative. The five role models of leadership in the Indian context reflect the Rama model, the Indira model, the Virat Purush model, the Ravana model and the Dadhiche model. The patterns of leadership anchored in the western context and the five role models of Indian context are intermixed and emergent styles of leadership are operative institutions provide role models for the young which are then carried forward and the resultant style is insufficient for todays tasks of educational institutions and large and mammoth organizations within the context of society experiencing flux and transition. The paper suggests leadership who represents and shares the values of sagacity, integrity, vision and relatedness with people and system simultaneously. A shift is required from a charismatic leader to an institutional leader who generates dynamicity and vitality in people any systems. In todays times leadership needs to create new traditions and paths and inspire people to a shared commitment to systems, tasks and policies and a sense of belonging and involvement.