Education is a global concern. The post-industrial society demand different skills and mind-set from their citizens. Transforming technologies bring new possibilities whereas education is still a highly low-tech sector. Current global economic crisis and political instabilities bring new problems to educational systems. These challenges also call for new solutions from education systems. These deep transformations reassure the importance of leadership in educational organizations. A line of inquiry in leadership studies has long been practiced under different labels such as leadership in relation to interaction patterns or role relationships with the followers, leadership in relation to the follower or the follower perceptions. With the advancement of more recent approaches to leadership such as transformation, culture and symbolic perspectives, leadership is now tended to be viewed as a culture creation process or a process of symbolic interaction to create better functioning organizations. For example, such questions have never been carefully dealt within the leadership studies: How are change and leadership interconnected in organizations? Is transformational leadership an always effective style of leadership? When do the organizations most demand transformational leadership? What are the organizational conditions that may call for a transactional style? What are the fundamental differences between transformational and transactional leaders in terms of their cognitive style? Through three propositions, the author attempts to answer these questions in this keynote speech.