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The purpose of this paper is to report on a follow up qualitative study with new principals in their second year on the job. The principals were part of a cohort of Aspiring Principals whose program preparation highlighted characteristics of leadership with a view to leading for change. The follow up study investigated principals’ experiences of the challenges of leading for change and sought stories of their success. The conceptual framework was drawn from the work of Michael Fullan (2014), Lyle Kirtman (2013) and Snowden’s (2005) Cynefin framework. The data sources for the study were interviews with principals. Findings from the study have implications for leadership development programs and leadership practice.