Both government reports and academic literature concur in claiming that the low standing of vocational education and training (VET) and the occupations it serves in the community is a major problem for increasing the engagement in this educational sector in an era of high aspiration. An initial analysis from a project capturing school students, school teachers and parents’ perspectives of what informs young people’s post-school choices found parents and teachers were key. Yet they often lacked informed and impartial exposure to or advice about VET and the occupations it serves. To identify whether this lack of familiarity was a key basis for shaping decision-making away from VET, a further analysis was undertaken drawing on the perspectives of vocational educators. That analysis showed, however, that exposure to VET and the occupations it serves does not, of itself, mean that the person providing advice is any more informed about or inherently encouraging of young people to engage in VET. Instead, vocational educators’ perspectives were more aligned with those of school teachers and parents of school-aged children than those of school students. The key finding here is that rather than relying upon the contributions that arise to engagement with familiars (i.e. parents and teachers), a process approach is required to provide impartial and comprehensive advice about and experiences with diverse post-school pathways and occupations to young people and to have mechanisms that allow their capacities, interests, and aspirations to be engaged with this advice.