Generational diversity provides a unique quandary for nursing leaders and educators to enlist, orient, and retain nurses. Millennials are the largest cohort since the Baby Boomers and the age group from which the nursing profession will build its future workforce. This study examined the experiences of the new graduate nurse of the millennial generation as they navigate orientation in an acute care setting. Using a Web-based survey to conduct the study allowed nurses from across the country to participate while providing easy access to the study questions. Analysis of the data through qualitative content analysis demonstrated a dominate theme of seeking structure while expecting an individualized orientation. The survey also revealed the importance of the preceptor and manager in the perceived success of this generation’s transition and a need to assimilate into the professional role of RN. Recognizing that there is a need to promote a more individualized orientation with improved mentoring for novice nurses and their preceptors is evident and challenges nursing leaders and educators to rethink current practices to retain new nurses. Established roles within the hospital and individual nursing units are changing and traditional strategies for recruitment and retention no longer apply. A structured orientation can facilitate the transition from new graduate to professional nurse and assist in the retention of qualified nurses and ultimately safe patient care.