This study examined the changes in the score of social skills, self-esteem, and basic fundamental work competencies —including the ability to take initiative, think thoroughly, and work collaboratively—of 352 inmates (300 males and 52 females) with a low-risk of recidivism in two Private Finance Initiative prisons in Japan. Scores from pre and post-vocational training were compared. A two-way repeated measures ANOVA, segmented by Time (Pre-training vs. Post-training) and Gender (Male vs. Female), was conducted for each dependent variable. Results revealed that inmates had significantly higher scores in fundamental social skills after the vocational training. Moreover, scores across all three basic work competencies—initiative-taking, thorough thinking, and teamwork—demonstrated significant changes at post-training. A distinct change in initiative-taking was especially evident among female inmates. This study suggested that vocational training in prisons may effectively improve inmates’ essential social skills and basic fundamental work competencies, preparing them for the workforce.