This chapter is based around the transcript of a session with a Year 7 student who is presenting with seriously challenging behaviour. The reader can examine in detail the flow of a SF conversation. Alongside is a running commentary that highlights the key SF principles and thinking underpinning the formulation of questions which respond to those parts of the student’s answer that are most closely commensurate with the possibilities of future difference. It is not an easy session and the reader will observe: how to persist with the best hopes question to establish a point of motivation for the student where the most potential for change resides; what works in detailing a preferred future description that is inclusive of the student’s preferred outcomes within the context of what the school will also be paying attention to; how to build a dialogue that weaves descriptions with relationships. The progress of students where there are challenges is rarely linear. The chapter also includes a follow-up session to illustrate how a SF approach can work with setbacks in a way that supports what is wanted, gives prominence to intention and helps define a ‘reputation’ that is most closely aligned to the preferred outcome.