Today's maritime transportation expects a high level of success from Seafarers, especially the captains of the ship. However, accident analysis has shown that sometimes basic information or correct attitudes/behaviors are not developed or applied at the right time. The maritime education, which has become standardized all over the world, ensures that the individual obtains the proficiency, but does not provide competence. The concept of competence is now being questioned for captains and captain candidates. It is an indisputable element for the captains who have the highest level of knowledge and attitudes and behaviors expected of him, especially for himself, his ship, his fleet and his company in emergencies. With regards to this knowledge, the main purpose of this study is to determine and analyze the differences between the expectations of managers and the actual experience, knowledge, and skills of fleet captains. To this end, in the simulator environment, potentially dangerous scenarios that may be experienced in only the course of navigation were developed. These risky and dangerous simulation scenarios have been developed based on real-life events and accidents occurring in the fleet of ship management companies. With this method, successful captains identified acceptable risk solutions for high-risk scenarios and developed the competence, knowledge, and skills necessary for similar extreme situations. Emergency Response, Communication, and Leadership Skills, Psychometrics, Competence and Decision Making are some of the data collected through simulation experiments. These data are data that can be used as a proactive management tool to reduce future risks of fleet ships. In practice, emotions of captains, high stress, loss of situational awareness, or emotions in real life such as anger have been seen and evaluated in simulation.