This chapter describes techniques for hypothetical reasoning, which plays a crucial role in the treatment of adolescents at clinical high risk (CHR) of psychosis. Our focus is primarily on cognitive distortions that promote paranoia or depressive symptoms. Unlike psychotic patients, CHR patients are generally capable of reflective thinking and can question their paranoid beliefs. However, many still struggle to recognize or modify delusional or distorted thoughts due to cognitive biases such as jumping to conclusions or confirmation bias. Therapeutic conversations that incorporate hypothetical reasoning can help to identify and challenge these patterns of thinking.