School administrators can not be expected to effectively embrace their roles and functions as school administrators without the appropriate support structures, resources, and administrative training in place at district level. Administrators, more than ever, must know, understand, and be prepared to meet the complexities and challenging demands the administrative position entails before considering the job. With the current school leadership shortage looming across North America, it becomes vitally important that school districts provide leadership training, ongoing professional leadership development and preparation for increasing the levels of effectiveness of aspiring and practicing school administrators. Through a review of pertinent literature this article explores how school districts are preparing their school leaders for their roles.