This book will focus on caring and caring leadership at both interpersonal and organizational levels. There have been very few treatments of caring as applied to school leadership. Most attention has been paid to caring among teachers and students. Moreover, most books in education on caring focus on the interpersonal dimensions of caring, the actions and interactions between the one caring and the one cared for. While the interpersonal is very important in our conceptualization of caring school leadership, this book will argue that caring in leadership cannot be fully understood nor its benefits fully achieved without exploring caring organizationally and without examining the role of leadership in cultivating caring among others and promoting aspects of school organization conducive to caring. This book is unlike many other books about school leadership practice. Readers will not find in this book “to-do” lists or scripts. Readers will not find compilations of strategies that are universally effective. This book is an exposition of ideas, principles, and values illustrated with examples of how to make school leadership practice more caring. We present caring school leadership as situational, dynamic, relational, and personal. There is no “one size fits all” for caring leadership. We eschew the notion of recipes, of telling readers specifically what to do. Instead, we present principles and possibilities to inform and inspire. A key feature of this book will be multiple vignettes of practice illustrating actions and interactions of caring and caring leadership in schools. We have collected nearly 40 first-person stories recounting acts of caring and caring school leadership from practicing principals, assistant, and associate principals and teachers. The authors will be collecting more of these stories as they prepare the final manuscript. These stories include both “hits and misses”, that is, actions and interactions that achieve the aims of caring and those that fall short. The authors will include summaries of arguments and take-away points at the end of each chapter. These summaries will be accompanied by study/discussion questions that will aim to engage readers more deeply in the content of each chapter and challenge them to consider this content in relation to their own practice.