With growing concerns over the workforce “skills gap,” additional insight is needed on the training and transfer of professional skills, particularly surrounding the transition from education to employment. This study leveraged latent change score modeling to examine the role of the Big Five personality traits, general mental ability (GMA), and training self-efficacy for predicting training performance and transfer, operationalized as change in performance ratings across two transition periods. Data were collected from Midwestern United States culinary students (N = 239) completing a 6-week capstone course and two consecutive 6-week externships during which they were evaluated on professional and culinary skills. Findings demonstrated complex relations with training performance, initial transfer, and subsequent transfer, such that GMA, conscientiousness, and openness/intellect (negatively) predicted performance in the training program, whereas GMA, neuroticism, and openness/intellect (positively) predicted change in performance between training and initial transfer. Implications for theory, practice, and the “skills gap” are discussed.