This paper presents the results of empirical research of the interaction between career motivation, self-monitoring and generational differences. Data were collected from 142 full-time newcomers of two organizations in Saint-Petersburg. The following questionnaires were used: the self-monitoring scale developed by Snyder M.; the career anchors scale developed by Schein E., which was extended by the patriotism scale from the culture appeal questionnaire developed by Snetkov V. as well as the organizational commitment questionnaire developed by Porter. L. Results indicate the self-monitoring and career anchors significant differences among three generations: Baby Boomers (1946—1964), Generation X (1965—1983), Generation Y (1984 or later) as well as their influence for on-boarding outcomes. This research shows that Baby Boomers and Generation X have more adaptable characteristics toward achieving organizational socialization. Generation Y is harder to integrate into corporate structures as this group has own social attitudes and assumptions about organization life.