House et al. (2007) finds that leadership and organizational culture are closely linked to each other as leaders influence the culture of their organizations. Research talks about a number of definitions of leadership but it is not easy to define. (E.g. Western, 2008; Yukl, 2010). However, Cohen (2009) critically analyzes the definitions of Dracker (1996), Eisenhower (1969), Northouse (2004) and finally summarizes the definition of leadership consisting of five elements. First of all, ask questions to establish direction, which means that effective leaders must listen to the voice of followers with respect and then share common goals and ideas with them. Additionally, leaders must seek information and allocate resources optimally; act ethically; allow your employees to work comfortably and effectively. This essay will explain the different leadership styles and how they influence organizations with examples of organizations and leaders with main focus on the well-known entrepreneur: Sir Alan Sugar. Rising from nothing to incredible success (£730 million), he is a legend in the history of British entrepreneurship; his reality show “The Apprentice,” a great recruiting entertainment, is a crowd pleaser for no reason. However, as a person he is controversial among people, probably due to his bullying or harassment (destructive) leadership style. There are four schools of leadership styles: trait, behavioral, contingency, and transformational. However, in the case of Alan Sugar, he has transactional traits and styles which will be explained in detail below. As Yukl (2010) indicates, such factors (e.g. personality, values ​​and capabilities) are attributed to a leader. It is normally widely recognized that someone is born to be a leader… a piece of paper… a man who allows others to think and act his way (role model) and his employees work him for unconditional loyalty (e.g. example, its PA), moreover, adopts a fair system of rewards and punishments; however, as a leader sometimes he just needs some transformative styles that respect and communicate equally with followers rather than force them into silence abruptly. Regarding organizational culture, the article deepens the understanding of some factors that contribute to detecting existing cultures in an organization, for example the communication system. Consequently, it can be identified that its culture can not only be classified as power but as task. Furthermore, due to the changing external environment, composite and flexible cultures appear to be a better way for an organization's sustainable development. Therefore, leadership is closely related to organizational culture.