A chief resident's role incorporates administrative, academic, and interpersonal responsibilities essential to managing a successful residency program. However, rising chief residents receive little formal exposure to leadership training. To (1) define leadership styles; (2) understand the effect of cultural competence on leadership styles; (3) learn effective methods to advocate as the chief resident; (4) provide effective peer feedback; (5) provide effective supervisor feedback; (6) learn effective conflict management; (7) ensure psychological safety. We developed a 1-day curriculum combining didactics and simulation activities for our program's rising chief residents. Implementation of our curricular design included a morning session focusing on small groups and didactic-based lectures on specific topics pertinent to leadership, along with a debriefing of a psychometric evaluation tool administered before the curriculum day. The simulation activity consisted of 3 group objective structured clinical examination (G-OSCE) scenarios: (1) providing a struggling junior trainee with feedback; (2) debriefing an adverse clinical outcome as the team leader; (3) navigating a challenging situation with a supervising physician. Standardized participants were surveyed for specific objectives. Learners completed precurricular and postcurricular surveys on their familiarity and preparedness for their chief year. Comparison of preintervention (n = 16) and postintervention (n = 10) data shows improvements in familiarity with leadership models (p = 0.006), cultural competence in leadership (p = 0.027), and team organizational structure (p = 0.010) with notable improvement in report of advocating for the team to 100% of participants in the postcurricular survey. In addition, although not statistically significant, familiarity with specific strategies for feedback delivery improved (p = 0.053), as did learner comfort levels with feedback delivery (comparing 51% of learners were either very or somewhat comfortable precurriculum to 90% postcurriculum). This is further supported by standardized participant data after the G-OSCEs. Although familiarity with wellness resources did improve across learners (p = 0.421), learner-reported use of wellness resources was noted to be reduced after the curricular intervention and remains a result of further interest for exploration. A 1-day leadership development curriculum combining didactics and simulation is an effective means of preparing rising chief residents to succeed in their transition to this leadership role.