Women govern differently and offer a distinct voice in the governing process yet remain significantly underrepresented among city managers and chief administrative officers. Despite decades of work to improve gender parity, women hold just 13% of chief local government positions according to the International City/County Managers Association (ICMA). One reason for this may be that women have different experiences and are socialized differently than men, as suggested by differing motivations, identities, and attitudes. Using a mixed-methods approach, we explore differences in the experiences and socialization of women and men that may contribute to the gender disparity in representation among city managers. Our study yields several significant findings that suggest women are mentored differently, develop different political attitudes over time, and develop confidence differently than their male counterparts. Contrary to prior research, we did not find significant differences in public service motivations by gender or year of service.