We explore the roles children play in the design and evaluation of technological tools in a formal educational environment. In order to do so, we describe two separate projects set in a formal educational context: primary schools, with children aged 8–10, in Switzerland (called PADS), and with older students, 11–12, in Scotland (called CHIS). In the first case the teacher and pupils were co-designing a novel application to support the creation of multimedia fairy tales, where in the second, students and teachers worked towards the definition of new tools to assist them in searching for information. The tasks were different but comparable in terms of complexity and level of interest expressed by children. Researchers followed a similar approach in order to interact with the stakeholders. We here describe the different attitudes and assumptions of the adults involved. In the Scottish study these encouraged students to make choices, propose solutions and work independently. In the Swiss study these aimed at supporting children use of digital media and artefacts for the creation of a digital fairy tale. Our investigation aims at getting a better understanding of the kind of roles and contributions young users could bring to collaborative design and how to better engage and motivate them.