Despite extensive discussions on leadership in today's world, this phenomenon still lacks continuous and updated analysis. When intertwining leadership with personality psychology, the issue becomes particularly interesting and challenging. The combination of these themes allows us to understand how personality influences leadership, encompassing skills, satisfaction, and resulting efforts. The general objective of the research is to examine whether there are trends regarding the relationship between the dimensions of the Big Five, leadership competencies, employee satisfaction, and extraordinary effort (criterion factors), to enhance the technical leadership selection process and maximize the exercise of leadership. A quantitative approach was adopted, using a competency and the Big Five Inventory questionnaires. Questionnaires were administered to a sample of 69 employees. Data analysis demonstrated that openness to new experiences is significantly associated with leadership competencies. Specifically, a statistically significant relationship was found between openness to new experiences and both employee satisfaction and extraordinary effort. Furthermore, leadership competencies were linked to key criterion factors, particularly determination and proactivity. In conclusion, this research aimed to highlight trends in the relationships between the Big Five personality dimensions, leadership competencies, employee satisfaction, and extraordinary effort, ultimately suggesting that understanding these relationships can enhance the company’s selection process for leadership positions and foster more effective leadership within the organization.