The study compares the perception and evaluation of school career guidance from the perspective of students (N = 1,614) and teachers (N = 242) at secondary schools in Saxony. The study examined the perceived career relevance of lessons, the teaching and classroom atmosphere, the use of practical learning methods and materials, key teaching characteristics (cognitive activation, relevance to everyday life, enthusiasm), as well as awareness, usefulness, and desire for career guidance measures. The results show clear differences between the two groups: teachers consistently rate career relevance, teaching quality, and classroom atmosphere more positively, while students are more critical and express more nuanced assessments. Practice-oriented formats (e.g., internships) are appreciated by both groups, whereas offerings with a gender-specific focus or little relevance to everyday life are rated more cautiously. In addition, there are significant gender-specific differences in the perception of individual measures and teaching aspects, particularly with regard to support, use of materials, and desired offerings. Furthermore, significant gender-specific differences are evident, particularly in that boys perceive the lessons as more career-oriented and tend to express greater confidence in their decision-making and self-efficacy, while girls are more critical of the relevance to everyday life, use of materials, and support, and more often desire additional offerings. The findings underscore the need to integrate more practical content, to design gender-sensitive approaches in a reflective manner, and to specifically align the perspectives of students and teachers in order to increase the effectiveness of career guidance in schools.