The focus of this paper was on the effects of trainee and organization characteristics on training outcomes of the Specialization courses. From the variables measured in this study, it was concluded that age is a significant factor in the performance of students in terms of actual grades received. However, it is not a significant factor when it comes to being a predictor of reactions and motivation to apply learning. Meanwhile, the length of service does not affect reaction and motivation to apply learning because reaction and motivation to apply learning are seen to be different across lengths of military service. Academic background, on the other hand, affects performance though it is seen to be insignificant in terms of reactions and motivation to apply learning.