This article explores how organizational cultures shape workplace learning for those learning to be educational leaders. The discussion is illustrated with the data from an ethnographic case study which explored the workplace learning of five school leaders. The findings suggest that workplace boundaries were constructed in response to perceptions of threat from the external environment and perceptions of risk in terms of school performance and that this had a significant impact on both what and how learning was taking place. These findings raise questions about how learners are able to develop creativity and innovation through workplace learning in a restrictive environment and the purpose of workplace learning when it is placed as a central feature of national leadership programmes. (Contains 2 figures and 1 note.)