The aim of this study was to examine the perspective of school administrators with regard to teachers from different generations. In this study, the strengths, weaknesses, opportunities, and threats of each generation were examined. This study was conducted as a Strength, Weakness, Opportunity, and Threat (SWOT) analysis. The study group consisted of 26 school administrators from the Dilovası district of Kocaeli province, Turkey. According to the school administrators, the Baby Boomer generation shows their strengths with discipline and experience, Generation X with determination, and Generation Y with their abilities in technology. As for the weaknesses of each generation, Baby Boomers are against innovation and disobedient of the management, Generation X claims to know everything, and Generation Y is inexperienced. What creates opportunities for schools is that Baby Boomers manage crises and transfer experience, Generation X acts as a bridge between the generations, and Generation Y applies new methods in education. For the threats of different generations to the school, the school administrators stated that Baby Boomers hinder innovation, Generation X is disloyal, and Generation Y is inexperienced and against the system.