The number of leadership education and development programs has increased substantially over the past few decades. However, deliberate assessment strategies aimed at understanding actual student development have not kept pace. The primary reason for this limitation likely involves the challenges that are associated with this type of assessment. When examining leadership one is not only interested in the mere acquisition and retention of knowledge, but the actual application and practice of such knowledge. There are a host of challenges that stand in the way of such assessment. In the present paper we call attention to several of these challenges in an effort to understand what effective leader education assessment could look like. Additionally, we offer two examples of how intentional assessment strategies can be implemented to evaluate the effectiveness of leader education and development.