This dissertation is designed to explore the leadership of female Chief Communications Officers (CCOs). This study first observes the types of leadership qualities female CCOs currently exhibit and whether those qualities are more representative of transactional leadership, transformational leadership, or a combination of both leadership styles. This study also uses Festinger’s Social Comparison Theory to observe how upward comparisons to other men and women in similar leadership roles and downward comparisons to lower–level male and female employees have an effect on self-evaluations conducted by the female CCOs. Through the use of Social Comparison Theory, this study observes whether female CCOs conduct these social comparisons to evaluate their leadership and whether they use the results from those evaluations to make any improvements to their current leadership style. Using a phenomenological research design, this study conducted in-depth interviews in order to observe the similarities and differences among the female CCOs from different organizational environments in regards to the driving factors and results of social comparisons on evaluations and improvements in leadership style. The findings of this study suggest the leadership of CCOs is contingent upon the advancements of the profession, c-suite expectations, and needs of employees. This study found female CCOs are actively practicing transactional and transformational leadership, since they believe qualities of both styles are beneficial for leadership effectiveness. Additionally, this study found gender does not significantly influence female CCOs. Instead, it was found these women are positively learning how to improve their leadership from the personality traits and attributes of other leaders and employees in similar and dissimilar positions.