As school districts have made improvements to teaching and learning, and raised student achievement in the process, reform-minded superintendents have usually led the way. When they move on, they leave a legacy of programs and policies that have worked. That is just where finding the next superintendent can get tricky. It is not easy when the previous superintendent has been a powerhouse reformer. Should the job description for a successor insist on keeping the methods that led to the district's gains? Are there particular programs and approaches that simply have to continue? What kind of school improvement agenda can the next superintendent bring apart from what has been done so far, and what kind of room is there for new ideas? These are just some of the questions that the Montgomery County (Maryland) Public Schools and Hartford (Connecticut) Public Schools wrestled with leading up to the respective departures of superintendents Jerry Weast and Steven Adamowski.