This case study research explores the potential of a post-16 pathway planning process based upon self-determination theory (SDT). Two male students at an alternative provision (AP), were supported by a behavioural support teacher to take part in a pre-planning meeting with the researcher to explore their post-16 aspirations. They then took part in a planning session within which the discussion and documentation were informed by SDT. A follow up conversation was held with the behavioural support teacher to feed back the contents of the planning sessions and support implementation of any outcomes. One student took part in a follow up interview, the other became uncontactable due to leaving the AP. The planning sessions and the follow up interview were transcribed and thematically analysed. Key themes were particularly consistent with autonomy and relatedness dimensions within SDT. Findings suggest SDT can provide a framework for post-16 planning, through facilitating exploration of goals and aspirations. Student follow-up suggested the process had been autonomy-supporting and a positive experience. Limitations, future directions, and implications for practitioners are discussed.