This paper aims to bridge the information asymmetry between the communities of S3 practitioners and evaluators by presenting relevant information to both sides on various aspects of evaluation design and the concept of smart specialisation, respectively. The document starts with a summary (largely addressed to the evaluators community) of the concept of smart specialisation and the reasons that pushed it in the policy agenda. It then considers the evaluation of smart specialisation in the context of the ESIF regulations for the current and the next programming period. Following that, the report introduces the key choices that have to be made upon formulating an evaluation strategy. It builds heavily on Guy (1996). The audience for this is primarily the community of S3 practitioners and specifically the technical bodies in charge of, among others, monitoring and evaluation activities. These observations are complemented by some very specific, S3-relevant, remarks on the tactics of running an evaluation and followed by some conclusions.