We assume given a set of behavioural models of computation (event structures) that can be extracted from specifications, processes, code and/or data depending on the application, and have labels containing additional information of interest (e.g., an integer variable representing a measure in the context of the computation). In this paper we present our vision towards a formal flexible approach to search for optimal traces of execution with respect to different parameters of interest (e.g., time, efficacy, cost and/or concurrency), enriched with a mechanism to understand the difference between (sub-optimal) traces and their formalisation as explanations. The underlying idea of the approach is to be generalisable and hence suited to tackle practical problems in a variety of domains from aerospace, automotive and automation industries, as well as systems and applications developed for healthcare. Our examples here come from a healthcare based context.