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Continuity and change have become crucial themes for the built environment and heritage buildings; also in the education and practice of architects. Embedding built heritage values into studio-based design education is a daunting new challenge that demands new didactic perspectives and tools. To address the dilemmas that come with design assignments for adaptive reuse, an experiment with new didactic analytical tools has been conducted in the Heritage & Architecture (H&A) architectural design studios at the Delft University of Technology. The analysis attempts to connect matter—physical structures—and meaning in a structured graphical process through predefined mapping exercises. Our aim is to introduce a step-by-step method for exploration that can form the foundation of values-based design from built heritage. Central to our multifaceted approach is a specially developed matrix that is meant to support design-oriented analysis of heritage buildings. This paper situates the H&A perspective on the adaptive reuse of valorised buildings within the heritage discourse and architectural design education in general and further gives insight into the didactics, the tools, their uses and initial results. After a critical reflection on our points of departure, based in an evaluation of results, peer discussion and student evaluation, we conclude that the applied methodology is instructive to the educational goals but also merits further development. One of the lessons learnt for future teaching includes allowing students freedom to discover values themselves. An important conclusion is that an earlier and broader foundation that engages the continuation of tangible and intangible heritage values in the ever-changing built environment is required in architectural educational practice.