Transition from school to employment is a critical period in the lives of students with disabilities which further affects the quality of their adult lives. For individuals with Autism Spectrum Disorders transition is particularly demanding due to numerous challenges associated with the nature of the disorder. For the professionals working with such students transition entails a complex long-term process of preparing the student for the life beyond school with the final aim of inclusive employment. This study seeks to investigate educators perspective on providing transition from school to employment by looking at three critical aspects: strategies, best practices and barriers. Four educators working in an inclusive mainstream high school were interviewed. The findings indicated that transition to inclusive employment was a challenge due to a combination of barriers arising at different levels: individual barriers associated with the nature of disorder, the barriers connected to the gap in expectation between parents and educators, barriers arising from established transition routines and barriers emerging from the society. Informants predominantly addressed barriers arising from the student (associated with challenges of ASD) by implementing a number of strategies (e.g., assessment, early planning, parental involvement). The most effective application of strategies educators identified as their best practices, whereas absence of some strategies, recognized by literature as essential for transition, turned into barriers.