This doctoral dissertation examines how leaders manage generational character issues among employees. The study focuses on leaders' perceptions of character differences portrayed by Baby Boomer, Generation X, and Generation Y employees. It aims to identify common character issues for each generation and leadership styles that help address these issues. A quantitative survey was administered to leaders from various organizations to gather data on their perspectives. The results provide insight into managing a multi-generational workforce and addressing misunderstandings between employees from different eras.