Parents are considered to be the main stakeholders for adolescents, helping them in their educational and career choices. Although theoretical and empirical studies have pointed out the links between career-specific parental behaviors and the career development of adolescents, there has been a lack of research in this area in the Czech Republic. One of the reasons is the absence of an instrument that would enable measurement of parental behaviors. Therefore, the aim of the present study is to provide a tool for measuring career-specific parental behaviors in the Czech environment — the Parent Career Behavior Checklist (PCBC) — to verify its psychometric properties and explore the associations between career-specific parental behaviors and selected demographic and school-related variables. The data collection took place in June 2017 and the participants were students in the Vysočina Region in vocational upper-secondary schools finishing with schoolleaving examinations or apprenticeship certificates (N = 501). Participant age ranged from 15 to 21 years (M = 17.19, SD = 1.10). The results show that the Czech version of the PCBC is an internally consistent and structurally valid tool for measuring two dimensions of career-specific parental behavior—(psychosocial) support and (instrumental) action. It was confirmed that mothers were more engaged in educational or career choices than fathers; mothers having tertiary education was an advantage for adolescents, which is reflected in increased support and action; and lower levels of support and action were perceived by adolescents who for various reasons were living exclusively with their fathers.