Indian organizations being part of the context of Indian society and culture reflect the juxtaposition of divergent, multiple and heterogeneous elements of two diverse cultures. One is the traditional agrarian culture of India and the other is the logical rational and technological culture of the west. This paper explores a historical perspective of shifts in Indian culture as well its impact on organizations. The shifts are results of adoption and enforced implementation of organization structures management systems and managerial role definitions form western models These are 1) shifts in relatedness between self and system, 2) shift in role locations, 3) shift in technology, and 4) shift in size and processes of relatedness. These four shifts contributed to the resultant value dilemmas for Indian organizations as well as managerial role taking. These value dilemmas are in terms of actualization of managerial role in the area of responsibility, authority, exercise of authority and leadership and the relationship between men and technology. The paper identifies the unique characteristics of India organization and managers and suggests that the juxtaposition of these tow cultures where the forms of one and the processes of the other operate in the same space and people leads to the value dilemmas of role taking. As such the new response and direction of both Indian organization and managers lie in the identification and understanding of the contribution of psychocultural context as well as the changing nature of the industrial environment. This process will lead to redefinition and redesigning of both individual roles and organization sets to design new frames and action choices to manage the flux of the two cultures and the resultant value dilemmas. Similarly, this process will contribute to the growth of shared values and perspectives which can mobilise commitment and involvement of organizations and managers for a relevant work ethos in India.