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This illustrative book considers the interface of business structures, contexts, and leadership building blocks to explore the contingent nature of leadership development in transgenerational entrepreneurship. Longitudinal case studies of 27 family firms in nine different countries provide a rich, global selection of leadership development insights by examining the roles of values, professionalization, leadership style and other contingent factors. The diversity of cases and chapters provides a rich foundation for insight into the pathways currently in use to develop the next generation leaders, illuminating the strategies and pathways of successful transgenerational family enterprises. By examining the available literature and one or more case studies, each chapter draws pragmatic conclusions, with findings that suggest the importance of focusing on leadership as a shared capability, transmission of values to maintain an entrepreneurial culture, the fit between professionalization and values to increase transgenerational potential, the need to address the structure of the business and the focus on parenting to develop next generations. This path-breaking book will inform family business researchers as they explore the ways in use to develop the next generation. Each chapter starts with a mini-case study focused on a dilemma related to leader development, making this book an excellent resource for educators in undergraduate, graduate, or executive programs