This study conducted an interview-based stress evaluation that considered the psychosocial models of work stress and verified the evaluation’s predictive validity. A four-stage assessment comprising a pre-survey, pre-interview questionnaire, stress assessment interview, and post-survey after one month was conducted with 50 Japanese workers. Additionally, 16 occupational health professionals provided stress evaluations based on recorded interview videos. Variables based on intraclass correlation coefficients (ICCs) were computed in multiple ways to compare the agreement among the evaluators. The generalized estimating equation (GEE) was conducted to evaluate the prediction models. The overall ICC among the evaluators was 0.58. The GEE revealed that the mean score of the evaluators in the interview-based stress evaluation significantly predicted psychological symptoms (β=2.02, p=0.019), burnout (β=0.77, p<0.001), and well-being (β=–0.64, p=0.007) one month later, even after adjusting for the self-reported stress levels measured in the pre-survey. The predictive validity of the proposed interview-based stress evaluation was confirmed. Although there are several challenges in standardizing this evaluation, semi-structured interviews are an effective tool for understanding work stress.