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Globally, middle leaders are increasingly responsible for leading teacher development in schools. Although it is well established that middle leaders make a difference to teacher learning, understanding the nuanced details of their situated leading has remained obscured by generic school policies and role descriptions. This paper examines how the shadowing method employed in a four-year Australian investigation of middle leading practices revealed the day-to-day contingencies enabling and constraining the ‘flow of influence’ from leading to learning. Shadowing afforded the study of this ‘flow’ in real time happenings as middle leaders went about their daily work. Results showed the interplay between informal and formal practices creating conditions for teacher learning amidst the hidden, generally taken-for-granted, work demands experienced by middle leaders.