Chatbots are increasingly used to automate operational processes in customer service. However, most chatbots lack adaptation towards their users which may results in an unsatisfactory experience. Since knowing and meeting personal preferences is a key factor for enhancing usability in conversational agents, in this study we analyze an adaptive conversational agent that can automatically adjust according to a user’s personality type carefully excerpted from the Myers-Briggs type indicators. An experiment including 300 crowd workers examined how typifications like extroversion/introversion and thinking/feeling can be assessed and designed for a conversational agent in a job recommender domain. Our results validate the proposed design choices, and experiments on a user-matched personality typification, following the so-called law of attraction rule, show a significant positive influence on a range of selected usability criteria such as overall satisfaction, naturalness, promoter score, trust and appropriateness of the conversation.