This study seeks to further understand the influence of personality on preferred leadership style by investigating the relationship between the Ohio State Model of Leadership and the 5-factor model of personality. Archival data, consisting of scores on the NEO PI-R and Leadership Opinion Questionnaire, and demographic information (age, gender, education level, prior managerial experience) for 296 job applicants was analyzed. Conscientiousness, Extraversion, and Neuroticism were hypothesized to predict Initiating Structure, whereas Agreeableness was hypothesized to predict Consideration. A correlation matrix was computed for all of the variables in the study, followed by several multiple regression analyses. Results revealed that both Conscientiousness and Extraversion were positively related to Initiating Structure; Neuroticism was negatively related, but its effect disappeared once the influence of the remaining factors were controlled for; Agreeableness did not have an initial relationship with Initiating Structure, but was negatively related to this construct after controlling for the remaining factors. Both Openness to Experience and Agreeableness were positively related to Consideration. However, a large part of the variance in Initiating Structure and Consideration scores could not be accounted for by the five-factor model. The findings suggest that personality plays an important, yet insufficient, role in predicting leadership preferences for Initiating Structure and Consideration.