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This paper provides an account of an ongoing project with an independent school in the UK. The project focuses on a strategy development intervention which, from the start, was systemic in orientation. The intention was to integrate simple systems concepts and approaches into the strategy development process to: address power relations in actively engaging a wide range of stakeholders with the school’s strategy-making process; generate a range of good ideas; and make the strategy-making process transparent in order to inspire stakeholder confidence in, and commitment to, it and its outcomes. This paper describes how seeking to meet these aims entailed a series of workshops during the course of which an awareness of the relevance, in our interpretation, of Complex Adaptive Systems concepts grew