This paper draws on evidence from our three-year Economic and Social Research Council (ESRC)-funded research study of the lives, careers, experiences and aspirations of Generation X (under 40 years of age) principals and vice-principals in London, New York City, and Toronto. More specifically, the paper examines interview evidence from nine school-based studies in which nine leaders and 54 teachers discuss their perspectives on leaders' care of their staff members. The evidence demonstrates that leaders and teachers both place a high level of importance on leaders' ability and willingness to be supportive, understanding, and approachable. Teachers also expect leaders to serve as advocates for and role models of good work/life balance. While the school-level studies take place in radically different city-based contexts, the expectation of leaders' care for teachers transcends different accountability and policy structures. Both groups focus their discussion on work/life balance and, more specifically, the need for leaders to understand that teachers are people with lives beyond school. The paper highlights implications for policy, practice, and future research.