Design of educational multimedia rarely starts from scratch, but rather by attempting to reuse existing software. Although redesign has been an issue in research on evaluation and on learning objects, how it should be carried out in a principled way has remained relatively unexplored. Furthermore, understanding how empirical research on information and communication technologies (ICT) should feed back into redesign remains difficult. The present paper addresses these problems from the viewpoint of carrying out pedagogical expert evaluations, in the absence of empirical studies of target learners, in order to generate recommendations for redesign. Firstly, redesign proposals should be based on a coherent reconstruction of pedagogical foundations of educational ICT (software, documentation). Secondly, redesign proposals should result from dialogue between stakeholders, such as future users, pedagogical experts, software designers, and deciders. To these ends, we propose a framework, called GESTALT (Goals, (E) SiTuations, Actions, Learners, Tools), as a ‘boundary object' for dialogical redesign. Within an activity theory approach, GESTALT is based on analysis of available tools, the actions they support, the characteristics of learners who perform actions, and pedagogical goals that could be achieved in specific situations. An illustrative GESTALT analysis of educational software is provided, principally from the viewpoint of pedagogical experts. Finally, the strengths and limits of GESTALT are discussed.