This paper aims to present the research findings on the perceptions, roles and implications of school leadership in the Singapore education system in relation to preparing students to be future-ready. This is an exploratory study that deploys a qualitative methodology. Data is collected through structured and semi-structured questions designed to elicit responses from school leaders undergoing leadership training. Data collected are coded and analysed. Broad emerging themes are presented as findings in response to three research questions. There is no single definition of what it means for school leaders as "leaders of future-ready learners in the 21st C." It comprises a multi-faceted concept of leadership imperatives in six broad areas of knowledge, competencies, and skills. These areas inform school leaders on the adaptations they need to consider in undertaking their roles as leaders of future-ready learners. The findings are informative and affirmative for aspiring and incumbent school leaders on what it takes for them to be "leaders of future-ready learners in the 21st C" in the Singapore Education system.