In this paper, I explore when and why workplace training facilitates the retention of firsttime workers from historically underrepresented groups in formal employment. I argue that training conducted by experienced socialization agents is effective at preventing such workers from dropping out soon after they are hired. I also argue that experienced socialization agents promote retention of this workforce by inculcating “work-readiness” learning needed to survive at work, concentrating on self-presentation, interpersonal communication, work-life separation and self-reliance. I develop and evaluate this theory using ethnographic, personnel and survey data on a sample of first-time women workers entering a large factory in India, and exploiting exogenous variation in their assignment to trainers with varying levels of experience. This paper contributes to the literature on organizational inequality by demonstrating that workplace training can successfully foster retention of first-time workers from historically underrepresented groups, through the agents delivering the training and content of training. It also contributes to the socialization literature by focusing on an understudied population of workers, thus highlighting the significance of individual socialization agents in training programs and the mechanism of work-readiness learning explicitly imparted in socializing newcomers.