The role of the school administrator has dramatically changed over the last few years and has become more complex and much more important. As education systems struggle with changes to curriculum and pedagogy, school administrators are often bogged down with the minutia of their daily work. At the same time as they are overloaded with detail work, they are expected to be innovative change agents for their students and their staff. As the baby boom generation moves through the work force, more and more experienced school administrators are reaching retirement age. Many new administrators are thrust into the role of educational leadership with little or no preparation. While many school districts offer training in administration, few offer the type of true leadership training administrators need. This work looks at the experience of one school district in Alberta as it struggles to come to grips with the dynamics of educational leadership and what is needed to develop the exceptional leaders that will lead our schools in the 21st century.