The theme of this paper aimed to illustrate the relationship between personality traits and leadership style selection within an organization. The first part of the paper extensively elaborated on personality, citing three fundamental approaches: lexical, statistical, and theoretical approaches to personality. Following this, three of the most well-known personality taxonomies were selected: the Big Five, HEXACO, and Eysenck's personality theory. As a contrast to positive personality traits, the author identified negative personality traits under the term "Dark Triad." The three components of the Dark Triad were elucidated, along with their main characteristics. In the leadership section, the roles and desirable characteristics of leaders and managers were discussed. The concept of leadership was thoroughly explained along with different types of leadership. Three basic leadership models were presented: trait, behavioral, and contingency leadership models. Recent research emphasizes contemporary leadership models, including charismatic, transformational, transactional, interactive, and servant leadership. Towards the end, the paper highlighted another topic increasingly linked to leadership in recent times, namely the role of women in management. It explored the reasons for involving women in management and the differences between the leadership styles of men and women. Additionally, the results of a study on the percentage of women in the management boards of publicly listed companies in Southeastern Europe were provided. After the theoretical discussion, the empirical section presented the results of a survey conducted via a questionnaire. The questionnaire comprised two parts. The first part investigated the Big Five personality factors, while the second part examined management style, categorizing respondents based on their task-oriented or relationship-oriented tendencies. The survey results were presented statistically and tabulated, categorized based on general respondent data (age, length of managerial tenure). In conclusion, this paper illustrates the role of a leader's personality traits on employees and consequently on organizational goal achievement. It demonstrates the advantages of certain leadership methods and outlines the steps needed to increase employee productivity and improve management efficiency.