Secondary school teams have identified that post-secondary planning tools are useful for Grade 12 students but feel that conversations with our learners need to be started closer to Grade 10. This way it is a journey of discovery for the student throughout these key years to make choices that best reflect their goals. Our teams recognize that choices about the employment or post-secondary need to be made by our students and are engaging in inquiry projects focused on preparing for the transition from Grade 12. As part of the Inclusive Learning Innovation Grant process this year, one of our school teams created planning tools to support discussions and planning with their students. The students gave valuable feedback indicating they appreciated the resource developed for transition planning but needed support in completing key steps and taking action with an increased level of independence. We are wondering how we may design useful tools and instruction that supports students in gaining independence and self-advocacy skills as they prepare for their post-secondary plans? This inquiry project is ongoing and is a meaningful collaboration between teachers and students.