Perfectionism is defined as the degree to which we strive for perfection. In the scientific literature this enigmatic personality trait is viewed as both good and bad. Perfectionism has been found to be a sub-factor of Conscientiousness, which is closely associated with work performance and leadership (Howard and Howard, 2001). In medical and psychological literature it is often associated with maladaptive behavior (Pacht, 1984). Perfectionism is often associated with setting unrealistic goals and feelings of failure and worthlessness. This is particularly true in research in the formulation of self-concept and the development of relationships with others. However, there is little research on the relationship of perfectionism to human performance in an organizational context. The present study looks at the relationship between perfectionism and quality, timeliness of work, performance related competencies and overall work performance. Claims supervisors from a large Midwest-based insurance company were assessed a Big Five Personality Theory instrument which includes a subscale measuring perfectionism. Manager ratings of performance and measures of quality and timeliness of case closings based on independent audits were also collected. The data was analyzed using both linear and non-parametric techniques. The results show the complex relationship between this trait and performance and relationships at work. The study makes recommendations for the future research of this trait and human performance.