Previous research over the past two decades has argued Kirkpatrick’s model ignored the work environment and individual factors influencing training effectiveness. A focus of this study is to investigate four levels of Kirkpatrick’s model with a focus on moderating the influences of individual and work environment characteristic variables, which are learning motivation, self-efficacy, motivation to transfer, and social support. In the present study, we used path analysis to test the hypotheses. The results of this study expand our understanding of the progressive causal relationship of reaction, learning, and behavior to results. In particular, this study confirms the influence of the individual and work environment characteristic on training outcomes and it has implications for enhancing training effectiveness. Although the result of motivation to transfer as a moderating variable has negative effects on the relationship between learning and behavior, social support directly affects behavior change after training and moderates the relationship between learning and behavior. Furthermore, future research on training evaluation should consider the training design variables beyond the training course that may have interfered with the training outcomes.