We conducted the 'Reverse Mentoring' to encourage executives and team leaders to think, play and consume like the employees of the millennial generation, who were born in the 90s. Mentoring was carried out six times in a two-to-one setting, in which two team members played mentor for one leader. With this mentoring activity, the millennial team members introduced the YouTube channels to which they subscribed, while also watching other channels that were suitable for the leaders. They also came to popular places together and shared their young sensibility. For instance, they shared how to experience small but certain happiness by visiting famous bakeries, and experienced the young generation's leisure culture such as escape rooms and craft shops. In terms of work, team leaders listened to the ways in which the young members preferred to work and engaged in communication. As the mentoring created a chance to exchange opinions from different generations and find something in common to empathize with, we will continue to conduct Reverse Mentoring so that employees of different generations can relate to each other.