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The changing educational landscape has ushered in new expectations and initiatives in the learning communities that demand continued development, efficiency, and sustainability for flourishing and so, mid-career leadership matters. Educational leaders are challenged to adapt and navigate through the tide of internal and external forces to create the best positive outcome for learners, educational stakeholders, and the learning community. The aim of the chapter is to provide information on how mid-career leadership professional development can encourage leadership perspectives, principles, practices, and collaboration to support learning and promote sustainability in educational organizations. What follows in the chapter: perspectives of leadership that act as a segue into a discussion on transformative leadership, in general, and within the context of education; educational leadership as integral for growth, knowledge, and skills that enable mid-career leaders to operate effectively. Mid-career leadership professional development and training are designated to promote personal and professional growth. The narrative inquiry guided this study. With this approach, the author collected data, using structured interview questions, from educational leaders in Jamaica, Canada, and America on how mid-career leadership perspectives, principles, and practices could engage educational leaders in the strategic direction of educational organizations. The transformational leadership framework guided this chapter. A purposive sample of fifteen participants (educational leaders, professors/instructors, and senior administrators) was used in the study. The participants have at least 6 to 20 years of working experience. The findings revealed that mid-career leadership and transformational leadership in educational organizations are embedded with capacity, training and development, and growth.

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