Contract grading provides graduate-level students with greater control and autonomy within the learning process. The contract grading approach requires students to take greater responsibility for achieving course learning outcomes as well as allowing learners to adjust the style and focus of assignments to meet their own unique needs and desires. Within this article, contract grading is applied to social work leadership education and explored as a parallel learning process designed to reflect some of the fundamentals of leadership in action while also teaching about leadership. A review of the scholarship of contract grading, an example of the application of the method, and a reflection on potential challenges that may result are also included in the article.