This chapter explores the theoretical foundations and practical considerations necessary for instructional leaders to improve student retention in higher education online courses by improving training of online instructors using autonomy-supportive principles. To improve instructional practice, faculty development programming should focus on the specific needs of online instructors by providing personalized learning opportunities and reflection. Using self-determination theory as a framework, the psychological needs of instructors engaging in faculty development can be addressed through autonomy (personalization), competence (achievement), and relatedness (support). The authors recommend utilizing digital badges or microcredentials to scaffold programming, including a three-tiered system of badging that builds toward a culminating credential. Autonomy-supportive faculty development programming will empower instructors to improve teaching practice, and better engage online students.