Digital technologies have enabled uninterrupted mass persuasive communications everywhere and anytime, aiming at convincing people to change their beliefs, thoughts, and behaviors. Research has shown that persuasive technologies are most effective when the messages and means are tailored to people’s recipients’ unique characteristics, particularly personality. Previous studies have thus investigated the one-to-one relationship between the Big Five personality traits and influence styles—the engines behind any personalized persuasive technologies. Prior investigations yielded partially inconsistent results, potentially because the Big Five at the trait level is too broad an instrument in characterizing individual differences. This thesis drills down from personality trait to personality aspect – the next level of analysis in the personality hierarchy. The present study examines which personality aspect is most sensitive to which influence styles, generating a matrix of connections between personality and influence. Notably, aspects of Agreeableness and Conscientiousness were found to be most strongly related to influence styles. The findings refine existing theoretical knowledge of the relationships between personality and influence style. Future designers could utilize these nuanced associations between personality aspects to create more personalized, and powerful persuasive technologies. Ethical implications of the findings are discussed.