This paper investigates the practical reasoning involved in compliance-related decisions, distinguishing between two scenarios where a state of affairs is evaluated in the light of applicable norms: ex post compliance checking and ex ante compliance choices. While the literature in legal reasoning representation is exclusively focused on compliance checking scenarios, i.e., simulating a digital judge, different factors seem to play a role in the inner deliberation of compliance choices. In this paper we investigate how human agents are influenced in their compliance choices by their own value ranking and risk assessment and how, in turn, the choice affects their preference among alternative interpretations of the law. We contend that contributions from the literature such as the value-based argumentation framework, while focused on ex post judgments, may be able to provide a comprehensive framework for ex ante compliance decisions. The main goal of the research behind this work is to achieve a comprehensive representation of legal reasoning that can be used as a reference for the explanation of automated compliance decisions.