In this era of constant change, principals need to be able to handle high levels of complexity in its governance and policy implementation. Planning ahead is not sufficient; being able to interpret and plan the future into strategic responses is a huge focus in educational development today. The Leaders in Education Program (LEP) is a 6-month full-time program, which aims to prepare highly capable vice principals and ministry officers in Singapore for principal-ship. This paper examines the value proposition and critical components of the LEP, and through a comparative analysis, it critically reflects on the challenges associated with this model. While the LEP has gained worldwide admiration for heightening participant's awareness of the interactive nature of the "roles" and "minds" of school leadership, this model is found to be "especially selective," attracting just 5% of the intended population. In order for a larger pool of school leaders to benefit, this paper recommends the "borrowing" of mentoring and networked learning structures to level up distributed and lateral leadership within and across schools. This should gradually develop a culture of leaders growing leaders as a way to ensure scalability and sustainability of leadership talent.