Results from a study examining the predictors of skill transfer from an instructional to a work environment are presented. Prior research indicates that skill transfer is a function of both individual and contextual factors. A total of 186 employees from a work organization were surveyed on individual dimensions (goal orientation, training self-efficacy) and contextual factors (supervisor and peer support). Pre-training motivation was proposed as proximal training outcome and further connected to the distal outcome, skill transfer. Analyses with structural equation modeling using EQS indicate that individual dimensions, such as mastery-approach goal orientation and training self-efficacy, are related to pre-training motivation. Also, contextual factors, such as peer support, predicted both pre-training motivation and skill transfer, while supervisor support was unrelated to either pre-training motivation or skill transfer. Pre-training motivation, in turn, was related to skill transfer. Implications for theory and practice are discussed.