In this chapter we report on a study into the organisational behaviour of teachers and middle managers in the Dutch vocational education and training (VET) sector. The fact that in 1996 publicly and privately funded schools for vocational education and training were brought together in one legal framework created a historic new situation in the Netherlands. Since that time schools with different institutional histories, goals and orientations providing vocational education and training have been embedded in a complex and hybrid environment. When comparing the organisational behaviour of teachers and middle managers in publicly and privately funded schools differences were found. The performed multilevel analysis and analysis of variance (ANOVA) show there are differences among teachers as well as among middle managers. The analyses furthermore reveal that teachers’ and middle managers’ attitudes to education seem to be affected by different factors.