This short research note discusses some of the challenges involved when undertaking qualitative research with ‘young offenders’, a neglected area within the methodological literature. By drawing on previous research with ‘young offenders’, the author discusses how the use of traditional face‐to‐face interviews produced a number of research challenges which are specific to the psychosocial, biographical and institutional contexts of this particular population. In attempting to overcome some of these challenges in her current research, the author developed a specific research tool – the assisted questionnaire (AQ) – and the remainder of this article describes how its use with ‘young offenders’ helped to overcome some of the methodological challenges which had earlier been identified.