School leadership en-route to a grand leap is defined as a cumulative progressive development process and an on-going process. This study discusses how a grand leap of a school was determined by the contextual settings of the school where emerging leadership readiness can shape the necessary behaviour patterns, together with leadership contextual intelligence. The results of this study suggest that external factors have dominance over the construction of the context. These contextual variations offer school leaders a reference to the immediate context, in turn, leading to the possibility of proposing initiatives to address any issues of concern or challenges encountered by leaders. This offered a new paradigm to develop a theory called "Referee Leadership Style" – enabling leaders to understand the immediate contextual variations for developing leadership effectiveness.