While research on the integration of play with work is growing, little is known about the implications of leaders adopting playful practices. When and why should leaders initiate play during work activities, i.e., playful work design? Drawing on social information processing theories and the wise proactivity framework, we developed and tested a theoretical framework that delineates when and why playful work design is wise and when it is not. This study focused on leader-follower dyads to examine (in)congruence effects of leader and follower playful work design on leader work engagement (leaders’ self-evaluations) and leader in-role job performance (followers’ evaluations). Results from 61 leader-follower dyads (n = 351 weeks) indicated that playful work design by leaders yields the most favorable outcomes in the weeks when their behavior aligns with that of followers. In the weeks when leaders’ playful work design exceeded that of followers, their in-role job performance was especially low. In contrast, when followers exceeded that of leaders, their work engagement suffered the most. Our research contributes to research on how leaders can manage their wellbeing, advances the social perspective of playful work design, and answers call for the potential dark side of play. This research offers a theoretical framework to explain when and why organizations should adopt or avoid playful practices.