A continuing challenge for the education system is how to evaluate the wider outcomes of schools. Wider measures of success – such as citizenship or lifelong learning – influence each other and emerge over time from complex interactions between students, teachers and leaders, and the wider community. Unless methods are found to evaluate these broader outcomes, which are able to do justice to learning and achievement as emergent properties of the learner’s engagement with his or her world the education system will continue to focus on narrow measures of school effectiveness which do not properly account for complexity. In this article we describe the rationale and methodology underpinning a pilot research project that applied hierarchical process modelling to a group of schools as complex living systems, using software developed by engineers at the University of Bristol, called Perimeta. The aim was to generate a stakeholder owned systems design which was better able to account for the full range of outcomes valued by each school, and for the complex processes which facilitate or inhibit them, thus providing a more nuanced leadership decision-making analytic. The project involved three academies in the UK.