Since the 1990s many strength-based assessments (for example, inventories, checklists, interview schedules) have been developed for use with children and young people, but these have offered a limited appraisal of the contexts in which strengths are present. In this study a new form of contextualised strength-based assessment was used within the routine practice of an educational psychologist. A multiple case study explored how this approach worked with eight children and young people referred to a local authority educational psychology team, ranging in age from 6.9 to 19.2 years. Qualitative data were analysed holistically using a story-board method. In all cases, participants identified situations or contexts which they associated with the presence of specific strengths. In some cases they highlighted aspects of a situation which might be hypothesised to have pedagogical value. There is discussion of the tensions that can arise in using this approach in schools when a more negative view of a pupil has already emerged. Nevertheless, the introduction of fresh information, about the type of contexts which suited specific children and young people, was helpful in providing ideas and recommendations which may have otherwise been missed.