The cultivation of intrinsic motivation is key in the twenty first century, but most students in Dutch vocational education lack this quality. To foster intrinsic motivation, a strong career-learning environment is needed that enables students to develop career competencies and a career identity. However such an environment is absent in much of vocational education in The Netherlands. Research shows that desired learning must be practice based (real life experiences are key), enable a dialogue (in order to attach personal meaning to real life experiences) and give students more autonomy in making choices in their school careers. Although there has been an increase in the use of portfolios and personal-development plans, these instruments are used mainly for improving success at school but are not in career and work. In addition, research on the conversations between student and teachers/work-place mentors shows that the latter talk primarily to (65%), and about (21%), but rarely with (9%) them. The culture in schools is still predominately monological. Most teachers feel uncertain about their abilities to help students in developing career competencies and a career identity, though a growing number of teachers want to be trained in initiating meaningful career dialogues. In order to make such training successful in terms of promoting new guidance behaviours, it is essential that school managers create a strong career-learning environment for teachers. The Standards Era policies (Gatto JT, Weapons of mass instruction. New Society Publishers, Gabriola, 2009) that dominate Dutch vocational education at the moment, however, leaves managers little space to do so.