A mentoring relationship occurs when a mentor gives a mentee personal support, professional support, or acts as a role model (Germain, 2011). Research has shown that mentors can positively affect their mentees (e.g. Karcher, 2008). Little research has focused on the qualities that make a good mentor. This study examines the personality characteristics and attachment styles of mentors and the effect they have on mentees’ leadership development, satisfaction with the mentoring relationship, academic success, and the college experience. Participants will be drawn from the College at Brockport’s Leadership Development Program which pairs students with a mentor. Personality characteristics will be assessed using the NEO-Five-Factor Inventory III. Attachment style will be measured by the Attachment Style Questionnaire (ASQ). Leadership development will be measured using the Socially Responsible Leadership Scale (SRLS). Two overall questions will be examined: what mentor/mentee personality characteristics are associated with significant developments in mentee leaderships; and whether mentees develop fewer leadership skills and have less satisfaction with mentoring relationships if mentors and mentees have different attachment styles.