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In personality psychology, the leadership role has become a more frequent topic, alongside topics on how organizations should be led and developed. Several theories regarding personality have progressed with the approach of covering what a “good” leader really is. This is based on the assumption that personality can predict work-related behaviors. The purpose of this study was to investigate the relationship between leadership ambition and personality traits. This to reach further knowledge on whether various personality measurements could be useful in understanding leadership and recruitment methods. This purpose was achieved in part by examining the correlation between self-rated personality and computer-generated personality based on cover letters of participants in a convenience sample. The correlation between specific personality traits and leadership ambition was further investigated. A web-based survey was used to measure these correlations, consisting of a self-rating scale for personality, alongside a statement that measured leadership ambition. Furthermore, personality was analyzed through computer-based interpretation of cover letters. Quantitative data were compiled and analyzed by using bivariate correlations. The results showed significant correlations between leadership ambition and self-rated openness (r = .128), extraversion (r = .268) and emotional stability (r = .126). In addition, a significant correlation between leadership ambition and computer-generated conscientiousness was found (r = .170). These results line up with previous research which indicate that certain personality traits are more prominent in those in leadership positions. The study has a practical value since it contributes to the understanding on how leadership and processes of recruiting could be developed in interaction with personality measurement methods.