The failure to implement policy has become a thorny issue in most organisations around the world and in South Africa. The blame for policy implementation failure has been placed on the lack of measuring readiness to implement in many organisations. The purpose of this study was to explore principals’ understanding of their readiness to implement the policy on the South African Standard for Principalship (PSSP). The PSSP is a newly published DBE policy that requires principals to implement it, which is why there is now a special focus on their understanding of how ready they are for its implementation. This study will contribute to the literature on readiness and policy implementation globally and within the South African context. The study used a case study research design and semi-structured interviews to gather information about the understanding of principals of their readiness to implement the PSSP. The study employed purposive and convenience sampling strategies to select fifteen principals to participate in the research. An invitation was extended to the principals through a consent form that contained information about confidentiality and the right to withdraw, which the participants were expected to sign before commencing with data collection. The main questions were based on how principals understand their readiness to implement the PSSP, their motivation to implement the PSSP, challenges of implementing the PSSP, factors that could contribute to the implementation of the PSSP, their capability to implement the PSSP, and their perception about the implementation of the PSSP. The data collected through interviews was transcribed verbatim. Data analysis was conducted through categorisation into themes and presented with direct quotations from the participants. The study showed that although principals have some level of understanding of the PSSP from personal reading, they have not received training on the policy, which resulted in the conclusion that the DBE has not yet established principals’ readiness to implement. Despite the lack of establishing readiness to implement on the part of the DBE, the study found out that principals have both intrinsic as well as extrinsic motivation to implement the PSSP. These motivators can be cancelled by the perceived challenges in implementing the policy. It was found out that principals perceive training and awareness creation as a possible solution to their little understanding of PSSP.