With seemingly fewer highly functional families, society is demanding schools that accomplish the impossible--higher standards and higher success rates. The current educational system cannot accomplish the impossible. The solution for the desired higher standards and higher success rates is not more programs or more technology. It is systems thinking followed by a system transformation. The education system of 2008 cannot produce much more than it does now. The reason education cannot produce what society desires is that the current system has flaws that must be identified and removed. Add-ons will not accomplish the transformation. Systemwide transformation means the root causes of problems are addressed and fixed. Instead of adding more programs, education needs new approaches to address the systemic issues. In this article, the author presents 12 questions that school district leaders must ask themselves before they dig for the root causes of what ails the school district.