Student engagement in medical education is progressing beyond passive participation in instructional activities toward embracing student empowerment that will develop independent and engaged healthcare professionals. This book chapter reorients the current understanding of student engagement by reviewing the importance of an institutional culture of empowerment and students as partners. We will provide concrete examples of groundbreaking leadership in student autonomy and empowerment undertaken at Southern Illinois University School of Medicine (SIU SOM), a recipient of the ASPIRE-to-Excellence Award in Student Engagement and the ASPIRE Stella Award Winner (The ASPIRE Stella Award is to recognize commitment to excellence in various areas. SIUSOM has received ASPIRE-to-Excellence Award in curriculum development, assessment, social accountability, simulation, as well as student engagement.) from the Association for Medical Education in Europe (AMEE). The coachability curriculum is a student-developed curriculum addition of intrapersonal and interpersonal skills. Some year 4 students choose to teach our year 1 students as tutors in problem-based learning (PBL). A reformed clerkship curriculum has abandoned shelf exams and instead focuses on clinical immersion and each student’s personalized education plans based on their educational needs. Programmatic assessment has been instituted that includes a progression committee that values and integrates student-adviser discussions and remediation plans. A recent initiative has developed an educational data dashboard system to embrace the institutional culture of student empowerment through transparency. The chapter concludes with ideas to facilitate an institutional culture of student empowerment.