Ever since the field of psychology has emerged, efforts have continued to explain personality in terms of different theories, models, and terminologies. Simultaneous to that is the line of devising and designing various personality testing and assessment methodologies. Defining personality in terms of different conceptualizations has been the ultimate aim of efforts by researchers to fill in the gaps in knowledge. However, the use of different assessment methodologies has attendant issues and raises many questions. Ranging from projective and semi-projective tests, through self-assessment and peer rating-based objective questionnaires and inventories developed using classical test theory, to the recently emerging situational judgment tests and application of item-response theory parameters, there have been enormous paradigm shifts in the methods of personality assessment. Although different researchers have provided inputs regarding the relative suitability and preference of one paradigm over the other, the question remains as to which paradigm explains personality optimally, and why any one particular paradigm should be preferred. Issues of relative psychometric advantages and disadvantages of each paradigm create a further dilemma in the minds of budding researchers. The present article is a meta-analytic synthesis of various personality assessment paradigms wherein the authors attempt to put forth all such challenging issues and try to find, and seek from eminent scientists, the answer to this dilemma.