This article highlights the importance of leadership engagement throughout the leadership learning process, adding to the leadership learning framework literature. We include a brief overview of leadership engagement as it relates to user-centered design (UCD), commonly utilized in information technology companies. The authors offer how UCD can assist in critically designing leadership engagement opportunities with a learner-centered approach. The authors also describe the intersections of leadership engagement and UCD to (re)imagine leadership experiences and provide recommendations and best practices based on existing and current practices. The article concludes with a detailed overview of how the Florida State University Fraternity and Sorority Life Department promotes leadership engagement through its initiatives and programs while centering the learner.