This book provides readers with insights into how Singapore school leaders are actively engaged in the transformation of the Singapore education system. It brings to attention crucial elucidations of the increasing demand and complexity placed on school leaders through the use of case studies. Each chapter in the book focuses on a particular issue which has become important or has gained renewed importance in the Singapore education system. The chapters first provide a background to the theme under examination and a theoretical basis for discussion. They then narrate the case that shows how school leaders interpret and implement policy initiatives in their respective schools or lead change in that area. The case studies span over a wide range of domains such as instructional leadership, assessment leadership, stakeholder engagement, professional learning communities, and school branding. The data collected from these case studies came primarily from interviews of educators in their respective school contexts, in addition to other sources of data such as artifacts. Each case study highlights descriptions, interpretations, and perspectives across school contexts, which is consistent with the proposition that school leadership is very much shaped by context. At the end of each chapter, there are guiding questions to help readers critically analyse and reflect on the main learning points of the case.