This paper utilises an interpretivist framework and recent developments in practice theory to examine the conditions which influence practices of socialising into the role of school principal in Trinidad and Tobago. The results indicate that for the 11 early career primary school principals, role socialisation occurs within complex "practice landscapes," where the practices of preparing classroom teachers for the principalship materialise within a context of contest. There is conflict between historical antecedents and the expectations and practices of socialising institutions such as the church, the school, the community and the Ministry of Education. This small-scale study has implications for leadership preparation practices and highlights principal socialisation as a challenge of context and history.