In this paper will be analysed three different educational contexts for preparing school principals such as Australia, England and the United States. This study analyses the professional development of academic leadership in the countries previously mentioned in order to apply the successful aspects to the Chilean education system, a system greatly need of improvement. The main finding of this study is that school administrator development is unproductive when the administrators themselves are not given the power to make decisions such as selecting teaching staff and managing finances. In this context, legal and bureaucratic structures in Chile act as barriers in consolidating and practicing these new ideas and recommendations.