More and more, the evaluation of complex projects is being related to the capacity of the project to deal with crucial social, economic, and environmental issues that society is responsible for and with the activation of systemic changes. Within this “mission” perspective, growing attention is given to learning in action. This paper aims at (i) conceptualizing a methodological framework for complex project evaluation within the context of the Triple-Loop Learning mechanism and (ii) showing its application in a European project as well as including the toolbox developed in coherence with the elaborated framework. It does so by looking at the case of an ongoing Horizon 2020 project aiming to develop language-oriented technologies supporting the inclusion of migrants in Europe. In particular, the paper looks at Triple-Loop Learning as pushed by the reflection on three dimensions: the “what”, the “how”, and the “why” of collective actions in complex projects. The consequent learning process is expected to have transformational potentials at the individual, institutional/organizational, and (in the long term) up to the societal scale. By exploring the opportunities offered by the evaluation tools in the easyRights project, the study highlights the potential of nurturing a wider, arguably neglected as yet, learning space for understanding, engaging, and transforming real contexts and thus developing more effective contribution to the needed transition.
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