Phishing attacks and other social manipulation attacks are an everyday occurrence for most workers in their email boxes. Others experience social engineering tricks to take and divert payments on legitimate electronic commerce transactions. This exploratory pilot study aims to examine the impact of user’s personality on the likelihood of user’s susceptibility to social engineering attacks. Five expert interviews were conducted to investigate what traits makes some individuals more or sometimes less susceptible to social engineering attack than others. The personality traits were obtained using the big five personality model for correlation with interview data. The result suggests that users with high scores in agreeableness and extroversion traits are likely to be more susceptible to social engineering attack than others. These results are a useful start for further research into the impact of different tricks on different personality types.