In response to the worldwide COVID-19 outbreak, an increasing number of people have been teleworking. Among the challenges of working away from the office is physical separation, which makes it difficult to collaborate as a team. This study highlights a set of team management capabilities of astronauts who work in extremely remote and team-centric environments—in space and on the ground. This specific operating style for astronauts is referred to as space-flight resource management (SFRM). This research examined the team management capabilities of astronauts that completed a training program incorporating SFRM skills in a remote working environment. The program involved an original board game developed as a training tool for NASA's moon base tabletop simulation to foster the experiential learning of SFRM skills. We conducted two training sessions with similar groups of ten students, quantitatively measuring the level of each skill, and then compared the results of the two sessions. We observed that the developed training helped trainees acquire remote team management capabilities, especially in their communication skills, cross-cultural intelligence, and situational awareness. The study showed that in addition to the learning effect, repetitions of such training could enhance remote team management capabilities, which are invaluable in the teleworking environment.