The purpose of this field study of 327 nonfaculty university professionals was to examine the joint relationship of conscientiousness and context on two dependent variables: motivation and participation in voluntary training systems. Drawing on the principles of person-by-situation theories of personality, this study examined how the relationship between conscientiousness and training is moderated by social cues and managerial status. The findings from a field study indicated that the relationship between conscientiousness and motivation to learn was moderated by the favorableness of social cues from coworkers and supervisors. Results also indicated the relationship between conscientiousness and training participation was moderated by managerial status. The findings bolster research on the importance of situational factors on the decision to participate in voluntary training. (Contains 3 figures and 4 tables.)