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Leadership is culturally contingent and the status and influence of leaders vary considerably as a result of cultural forces in the countries or regions in which the leaders function. And not only cultural but also economical transition has impact on leadership. During the last fifteen years Estonia has transformed from being an authoritarian, centralized, totalitarian socialist state, to a democratic country with a free market economy and different attitudes and values. During economic transformation a complex set of normative and operating principles, embodied in historical structures, systems and practices becomes replaced by another unknown set, providing its members with a very ambiguous and uncertain period. the challenge has been to internalize a new type of organizational behavior in order to operate successfully under unfamiliar conditions. During this period of transformation actors, including top managers had to learn to deal with the discontinuities of the institutional environment. Authors analyze leadership styles of top managers of Estonian companies by using different theories of leadership as theoretical framework. The analysis is based on empirical data from international GLOBE study initiated by Robert House. GLOBE is a long-term project directed toward the development of systematic knowledge concerning how societal and organizational cultures and subcultures affect leadership and organizational practices (House et al. 2004). It includes a short CEO questionnaire on management preferences and strategies. In addition, a number of up to nine followers have been asked to describe the leadership style and behavior of their CEO with a questionnaire from the GLOBE. Questionnaires were translated and re-translated into Estonian language. The questionnaire asks for leadership behavior, trust and confidence of the followers, and their perception of the objectives and strategies of the firm. 53 questionnaires completed by the CEOs and 324 questionnaires were completed by subordinates. First, the content analysis of interviews was done, in order to find out leadership styles. Second, cluster analysis was performed by cases to classify CEO-s. Statistically significant differences were found out by using ANOVA test. The content analysis of interviews brought out following styles: autocratic style (15% of respondents), transactional style (31%) and transformational style (48%). There were also some traits of authentic and servant leadership. Authors develop implications for leadership development in countries in transition.