The purpose of the research is to find out which job skills Greek graduate students of high school and their parents consider as important qualifications for the youngsters' entry into the active working life with regard to their gender. The sample, consisting of 215 graduate students of high school and their parents (210), evaluated the importance they think the examined job skills have for the students' future entry into the labor market and also the extend to which the youngsters possess these skills. Results have shown that there were significant differences between students' and their parents' opinions with regard to gender concerning job skills that are considered as important for finding a job. This was also confirmed by the factor analysis applied. Significant gender differences were also found concerning the degree to which teenagers possess the examined skills. In concluding, male young students and their fathers believe that skills related to self-management, self-discipline and the use of technological means are more important for finding a job, whilst female young students and their mothers outline a more positive and social profile, confirming typical and stereotypical attitudes and vocational choices. (Contains 5 footnotes, 4 figures, and 5 tables.)