Drawing this symposium together, this final paper details reflections on the evaluation and implementation for the Differentiated Support for School Improvement initiative (DSSI), and in particular how the reform and the evaluation not only responded to new challenges, disruptions and demands over the four-year period but also how it added value to the field of evaluation and educational policy. It is argued that the potential for the evaluation to inform and add value to the implementation of DSSI is just one of the features which could position it as ‘transformative’. The evaluation methodology was constructed and employed through multiple methods, broad data links, and varied procedures to ensure triangulation of evidence. Systematic collaboration with the commissioner and education stakeholders assisted in the facilitation of a multi-transformative evaluation, that had an impact on the implementation of the initiative as well as influencing other educational school improvement reformsThe premise is that evaluations that utilise a collaborative approach not only have a greater sense of validity and are useful to the commissioner, but they also have a much greater likelihood of achieving transformation. Such an approach, however, does not exist without challenges such as impacting on the roles of the commissioner and evaluator, the relationship to the broader policy development, considerations for data sharing and objectivity of judgements that are made. The paper will explore these challenges and other unintended consequences. It is suggested that the DSSI evaluation process provides a valuable model for educators and evaluators to consider the idea of educational evaluation as more than an accountability mechanism but as an approach to continuous improvement of any policy or program.