Background & Aim: In Taiwan—where the collective tends to be prioritized over the individual—gentleness, sacrifice, and obedience are prized qualities in the overwhelmingly female nursing workforce. Nevertheless, role changes and overlapping hierarchical boundaries often lead to stress. This study examined the role transition experiences of female novice head nurses in Taiwan. Methods & Materials: This study adopted an approach of hermeneutic phenomenology. Purposive sampling and snowball sampling were used to identify participants on Facebook who met the inclusion criteria. Considering the study purpose, the sampling criteria were as follows: female, seniority of an incumbent head nurse of 6–30 months, ability to communicate in Mandarin, willingness to participate in the study, and willingness to participate in recorded interviews. Nurses working at the same hospital as the researcher were excluded. The participants were interviewed to gain information regarding their experiences during the role transition process. Results: Ten female novice head nurses were recruited. The adjustment process of novice head nurses revealed the hierarchical culture of Taiwanese nursing. During this process, the participants encountered conflicts in role transition, adjusted their approaches, established their roles, and achieved professional success. The introduction of Western management styles to Taiwan inevitably creates cultural conflict that complicates the transition of novice head nurses into their new roles. Conclusion: Nursing organizations must consider cultural factors when helping novice head nurses transition to their new roles. Support systems and role models should be provided to help novice head nurses navigate the transition to their new roles.