The research project, funded by the German Ministry of Education and Research, aims to shed light on the improvement strategies of eight improving high poverty schools in Germany. The case study is based on a multi-perspective reconstruction of school development strategies in four schools that have managed to attain good learning and performance outcomes against the odds, and four schools that have poor learning and performance outcomes as expected. Such a sample allows for a contrasting comparison of schools that start with comparable disadvantageous conditions, but differ with regard to the results and effects of their work. The project uses a multi method approach (document analysis, questionnaire survey, semi-structured interviews), with the purpose of gaining different perspectives on working processes in the eight case schools. The presentation focuses on results regarding the question how school leaders initialize and support individualized learning arrangements in everyday schooling. Therefore the findings of the single cases of the two groups –good schools against and weak schools in line with the expectations– are juxtaposed and contrasted systematically.