Multi-academy trusts are groups of schools in England led by an Executive Head Teacher and a Board of Trustees. High profile failures of these organisations raise questions over the way they are strategically led. Leadership studies argue that the absence of strategic thinking is a major detractor from performance & sustainability. However, creating strategy for a single organisation is very different to creating it for a collaboration. This article adopts a schema-based approach to examine the ways in leadership boards approach strategy as learning. Drawing on 42 qualitative interviews it asks: What evidence is there that strategy is a learning activity; What organisational implications are there for this? What are the implications of this for Trustee and CEO development in this area? And what theoretical contribution does this study make to what is known about strategy learning in multi-level organisations? The paper concludes that there is evidence to suggest that respondents view strategy as learning, whilst also suggesting areas for professional development for school leaders. From a theoretical perspective, the paper adds to knowledge on the role of metacognition in a strategy as learning approach to strategic decision-making.