The quality of organizational leadership can have a significant impact on organizational success and employee well-being. Some research has shown that leaders with secure attachment styles are more effective leaders, but the connection between different attachment styles and different leadership styles is unclear. Relationships between attachment styles and leadership styles were examined in this study. University personnel completed the Relationship Questionnaire and the Multifactor Leadership Questionnaire. Pearson correlation and multiple regression analyses revealed positive correlations between transformational leadership and secure attachment and negative relationships between transformational leadership and insecure attachment styles. Results of this study may help leaders recognize the relationship between their attachment style and their ability to increase organizational effectiveness and to decrease turnover.