This paper outlines a technique for enhancing the effectiveness of careers thinking by identifying and challenging tacit beliefs about career success. These beliefs can be understood as social scripts, i.e. cognitive structures that simplify common decision scenarios. An important contribution of careers counselling is to enable clients to recognise tacit beliefs and assumptions that limit the effectiveness of their careers thinking. In the process, this often involves finding problems. This paper outlines how an archetypal problem finding technique--Socratic inquiry--can be adapted and applied in this particular context. Socratic inquiry can enable identification of social scripts which are a source of limiting assumptions. It can also enable cross-examination of these assumptions, and enhance the facility for internal dialogue.