Engineers are a highly qualified population that is highly sought-after by organizations that are aware of the need to retain them in order to remain competitive in an increasingly competitive market. This is why their study represents an important issue for companies. The purpose of this study is to investigate the socio-demographic, professional, and individual characteristics influencing career success in Generation X (35–50 years) and Generation Y (24–34 years) engineers, and to highlight the differences between these two cohorts. For this purpose, we have a sample of 758 employees who graduated from French engineering schools and use a method of interaction effects analysis. The results confirm the link between objective and subjective career success and identify differences in the career perceptions and expectations of engineers from generations X and Y.