To explore when and why workplace training facilitates the retention of first-time workers from historically underrepresented groups in formal employment, I combine ethnographic fieldwork at an Indian garment factory employing first-time women workers, personnel data over a two-year period, and survey data from a sample of new hires. I find that training is effective at preventing first-time women workers from dropping out soon after they are hired when it is conducted by trainers with many years of experience. Rather than focusing only on job-specific skills, training conducted by experienced trainers includes the basic work-readiness skills of self-presentation, interpersonal communication, work–life separation, and self-reliance needed to survive at work. I find that first-time women workers quasi-randomly assigned to experienced trainers had about a 20-percent greater probability of being retained after three months, and these workers reported that they felt more ready for work than those assigned to less-experienced trainers. My results imply that for the majority of workers from historically underrepresented groups who are entering the workplace for the first time, training is important to foster their retention, and organizations that focus on both the attributes of the people delivering that training and its content have a greater chance of keeping these workers for the long term.