This study aimed to clarify the role of facilitation in transferring gaming and simulation experiences to the real world for varied participants. First, Kolb’s learning style was revisited to understand participants’ diversity in terms of gaming and simulation. Second, the role of facilitation was examined based on Kolb’s learning cycle, highlighting that participants can go through the cycle smoothly with the help of facilitation. Third, a case study of a product management game was shared, where team performance and participants’ attitudes were analyzed. For educational purposes, the facilitator must pay careful attention to the difference in each participant’s learning style, which makes them go through learning stages with varied manners. The case study showed that strategic instructions were effective for adjusting the difference in understanding among participants and making intensive discussion possible with the help of semi-autonomous grouping. The importance of appropriate facilitation is discussed to enhance participant learning cycles and transfer gaming and simulation experiences to the real world.