The process through which an insider to an organization can be described or classified is lined within the orthodox paradigm of classification in which an organization considers only subject with requisite employee criterion as an insider to that organization. This is further clouded with the relative rigidity in operational security policies being implemented in organizations. Establishing investigation process in instances of misuse occurrence and or ascertaining the efficiency of staff member using such archaic paradigm is maligned with endless possibilities of uncertainties. This study, therefore, proposes a holistic model for which insider classification can be crystallized using the combination of qualitative research process and analysis of moment structure evaluation process. A full comprehension of this proposition could serve as a hinge through which insider misuse investigation can be thoroughly carried out. In addition, integrating this paradigm into existing operational security policies could serve as a metric upon which an organization can understand insider dynamics, in order to prevent misuses, and enhance staff management.