The current study aims at investigating the effectiveness of a group career guidance program based upon the social cognition career theory in developing skills of personal maturity and career skills associated with entrepreneurship among 11 graders. The sample of the study included 120 students from two single-genders was divided randomly into two groups of 61 as a control group and 59 as an experimental group. The experimental group underwent a group guidance programs while the control group did normal career guidance activities. The study depended on the experimental method. The researcher constructed two measures with appropriate psychometric properties to be used in the current study; the Skills of Career Personal Maturity (SCPM) Scale and the Career Skills (CS) Scale. The SCPM has 36 items distributed over four factors: self-efficacy, selfawareness, risk readiness, and responsibility taking. The CS scale has 36 items distributed over four factors: innovation and creativity, solving career problems, taking career decision, and contact and communication. After verification of the validity and reliability of the scale which amounted to (0.85). The Career Personal Maturity reached (0,857) while the Career Skills reached (0,854). The study used a quasi-experimental research design. A 2x2 MANCOVA showed statistical significant differences between the experimental group and the control group over all factors of both the SCPM and CS scales favoring the experimental group. A 2x2 Mixed Design MANOVA showed that there were statistical significant differences in pre-test and the post-test for the experimental group in the guidance program over only three factors of the SCPM (self-awarenessself-efficacy , risk readiness,) in order. The results showed no significant statistical differences in responsibility taking . That may over all factors of the SC scales favoring the post-test taking career decision, contact and communication, innovation and creativity, solving career problems in order. The differences didn't get influenced by the students' gender and the time of application ( before program – after program ). The findings were discussed in the light of the theoretical framework and the previous studies .The study came out with a number of recommendations and suggestions based on the findings of the investigation process.