Parents are major partners in helping adolescents prepare for a career choice. Although several studies have examined links between general aspects of the parent-adolescent relationship and adolescents' career development, little research has addressed the mechanisms involved. This study aimed to validate a three-dimensional instrument for the assessment of parental career-related behaviors and to examine their associations with career exploration and decision-making difficulties. After testing the dimensional structure of the instrument, we examined the relationship between parents' behaviors and adolescents' career development by using data from 359 German adolescents who reported the amount of perceived parental career-related behaviors and their career exploration and decision-making difficulties. The results of structural equation modeling confirmed the hypothesized dimensional structure (support, interference, lack of engagement). While parental support associated positively with career exploration, interference and lack of engagement associated with decision-making difficulties. Furthermore, interference and lack of engagement moderated the relationship between support and exploration. Support moderated the association between interference and decision-making difficulties. (Contains 3 tables and 2 figures.)