This paper draws on a formative evaluation of the Engaged Action Learning pilot designed and developed in partnership between Lancaster University Management School (LUMS), Pfizer Pharmaceuticals, The NHS Leadership Centre and the Improvement and Development Agency. Firstly we provide some background to the challenge for designers in the move towards cross sector collaborative working Secondly, we address the implications for evaluators. We conclude that multi-stakeholder evaluation should move towards enabling ordinary people to get some things right and others wrong so that collaboratively we might make progress on important issues. The pilot forms part of a wider three year programme of action research with a broader range of partners aimed at deepening understanding of contemporary leadership challenges and developing effective approaches to leadership and management development. The project is not complete and the questions, reflections and initial conclusions outlined here are to be further developed in the context of the research programme