The primary goal of Systems Engineering is to develop a solution that best satisfies the needs of stakeholders. Validation is the process of checking if the developed solution satisfies the needs of the stakeholders. Current validation practices are heuristics-based and lack mathematical foundations, which may lead to suboptimal validation strategies. To ensure the correct and accurate validity of the system of interest, several artifacts throughout the system lifecycle must be considered, including but not limited to stakeholders’ needs, requirements, design, verification, etc. This paper characterizes validation in terms of these artifacts by proposing novel theoretical insights using Propositional logic as the foundation. The mechanism of representation for stakeholders’ needs plays a significant role in performing validation. This paper discusses the challenges associated with using existing textual stakeholder needs and preference functions with respect to validation in relation to the theoretical insights proposed. In addition, this paper highlights how the previously developed Modal preference logic can be used as an effective mechanism to develop a normative approach to validation in Systems Engineering.