This work draws a parallel between the leadership styles and their impact on the Small Family business Performance. The choice of studying this business world starting from the premise, supported by the literature review of Situational Leadership, that the leader play a more intense role in this segment. Therefore, based on two comparative cases of studies, were analyzed two small family business of commerce branch, chosen deliberately because of the differences in their leadership styles identified: transactional and transformational. These two cases were analyzed based on primary source data (leadership interviews and questionnaires with employees) and secondary data (company desk research) where we tried to relate the influence of these styles in the marketing positioning, financial matters and organizational climate. The results were compared with the literature and the works conclusion agree that the transformational leadership style leads to more effective results, although there are no casual relationship to financial performance and positioning market performance in a small family company and the leadership styles, as other organizational variables also has a strong influence in this process.