Phishing e-mails are the stepping stone for many cyber attacks exploiting the psychology of the victims. However, the literature lacks a study that correlates these phishing e-mail contents and the personality traits of the victims. By understanding how different types of phishing e-mails are crafted to exploit a population of certain personality types, one can develop a system that can predict which types of phishing e-mails a person might be more susceptible to. In this paper, we outline the architecture of such a decision support system based on five factor model of personality traits and a phishing experiment creating a virtual stock market, which can be used by an organization for personalized phishing awareness training of employees and better defense from phishing attacks.