This study aims to show the path taken by women leaders in the organization where they work, investigating the difficulties and challenges faced by them in order to achieve personal and professional projects. The chosen topics for the theoretical basis are: Diversity in leadership, which addresses the use of attributes of both genders in business management and Career, work and family, which features new family configurations and the economic and social changes in the workplace. To collect the data, six managers were interviewed individually. The analysis of the dialogues was performed through four categories: Career Planning; Work and family; Leadership style and gender characteristics of leadership from the point of view of a man leader. Finally, the data showed that in order to build and have a successful career, lots of study, effort and self-development are required. They live the conflict of knowing how to balance personal and professional life and they worry about performing well in several figures - woman, mother, wife and manager. They show characteristics of sensitivity, flexibility and partnership in team work, being strict and objective when the situation demands. There is a need for further observation in leadership styles, connected with a dichotomy of male and female behavior profiles when managing.