Unmanned aerial vehicles (UAVs) are becoming a hot topic in the last few years for several research areas, such as aeronautics or computer science. Big companies such as Airbus or Amazon aim to incorporate this technology to their current systems to improve the quality of their services while reducing the human costs. However, current UAV technology requires a strong human supervisory control and this supposes an important potential risk. Therefore, it is critical to keep track of the pilot behavior to be able to determine whether he is ready or not to operate with this technology. To deal with this problem, we have developed a methodology based on different performance metrics to automatically evaluate planning and monitoring skills of new users trained in a multi-UAV simulation environment. This methodology, based on unsupervised learning and fuzzy logic, can automatically generate a profile of future operators and use it to assess their skills.