Leadership development programs are gaining significant presence on college and university campuses. However, little rigorous research has been directed toward these developmental programs, and it is unclear whether they have any sustained impact on students’ leadership capabilities. Leadership development theories and research are reviewed and the conclusion drawn that the capability to reflect, to develop self-awareness and moral perspective are critical developmental skills. A central issue here is that which has been raised by Plato some 2364 years ago is still valid today and can contribute with real improvement in our development schemes. The issue is that of the art of leading others goes through the art of leading oneself. Using Plato’s teaching and other theoretical experiences particular challenges of facilitating the development of these skills in millennial students is discussed. A challenging focus on the art of leading others through the art of leading oneself is suggested.