How can educators use games and playful interactions to enhance the practice of skills related to leadership and management? Effective leadership involves a number of skills, such as strategic thinking, perspective-taking, critical thinking, ethical thinking, resource management, and reflection on one’s biases. In this article, we will review how three different instructors use games and play in their higher education classrooms to teach critical leadership skills. We will share how we use three different types of games: (1) a commercially-available off-the-shelf digital game ( Democracy 4) to enhance resource management and ethical thinking skills; (2) a non-digital card game ( @Stake Game) to teach critical thinking and argumentation; and (3) an independent (indie) digital game ( SweetXHeart) to teach bias reduction and perspective-taking. We will share best practices and recommendations for using games in leadership and management education.