With a great wave of baby boomers retiring, school leadership is in the midst of a generational shift. At the same time, schools themselves are changing with rapid technological advances and a new 21st century focus on, among other things, STE(A)M, project-based learning, blended and online learning, innovation, mindfulness, global education, and social-emotional intelligence. Author Debbie Freed has been facilitating heads' dialogue groups in the San Francisco Bay area for 25 years and consulting nationally. In those years she has observed leadership transitions closely through many school foundings, retirements, deaths, premature departures, unexpected crises, and turmoil, as well as through carefully timed and seamless "passings of the torch." All of this has informed her consulting practice and has solidified her belief that systems thinking and understanding the presence and power of institutional history and culture are essential in managing successful leadership transitions and in leading institutional innovation and transformation. Here Freed offers a discussion of the large number of turnovers, in school leadership, and gives advice for smooth transitions. [Online Feature]