Personality is increasingly used in the field of management and in the business of the organization. The importance of the leader's personality in order for the organization to function successfully was observed, as well as its influence on the choice of a particular leadership style. Personality traits can let us know in advance how a certain person will behave and in this way we can predict whether that particular person would be good as a leader. Among other things, personality affects the interaction between leaders and subordinates. In addition to personality, an individual leader is also characterized by the leadership style he applies. There are a number of leadership styles, and today where situational factors are constantly changing, quick adaptation of the leader and at the same time of his followers is extremely important. In order to implement this as successfully as possible, the leader's personality is important, as is the leadership style that will be applied in order to respond to changes in the market as efficiently as possible. This paper theoretically explains what personality is, how it is measured and what personality taxonomies are, but also what leadership is and what leadership models exist. At the end of it all was investigated the connection between the leader's personality and the leadership style applied in his organization, as well as his tendency to choose a workplace.