Members of Generation Y in the training and development industry will be required to assume leadership roles as Baby Boomers retire, yet little empirical research exists regarding how best to prepare them for leadership. The purpose of this study was to examine differences in leader developmental readiness between generational cohorts in the training industry, specifically Baby Boomers, Generation X, and Generation Y. Leader developmental readiness provided a definition of developmental readiness for leaders using the five constructs (learning goal orientation, developmental efficacy, self-awareness, leader complexity, and metacognitive ability). A volunteer sample was compiled from members of the ASTD National LinkedIN group (n = 636). Results were analyzed using structured means analysis with maximum likelihood (ML) estimation. Generational cohorts demonstrated differences in leader developmental readiness. Baby Boomers indicated statistically and practically higher metacognitive ability and developmental efficacy than Generation Y. Results demonstrated statistically and practically higher leader complexity in Generation Y and both Generation X and Baby Boomers. These results should inform leader development practitioners as they continue to use existing methods in preparing the different generations for leader development interventions while pointing to possible needs to increase the metacognitive ability and developmental efficacy in Generation Y and ensure accurate perception of leader complexity in those individuals. Further research would be helpful to confirm or refute findings and expand on the target population for enhanced generalizability.