<p>Reports from the United States underscore the vital role of chief residents in clinical practice and medical education, serving as leaders for their fellow residents.<span><sup>1</sup></span> While early leadership experience offers numerous benefits, a significant challenge persists in Japan: leadership positions remain predominantly held by men. Beyond leadership roles, Japan grapples with a pervasive gender gap within its medical field. For instance, the proportion of female physicians in Japan is the lowest among OECD countries, standing at just 23.6%.<span><sup>2</sup></span> This leadership disparity extends across hospital executive boards, professional societies, and academic institutions, limiting diversity at decision-making levels.</p><p>At the JACRA (Japan Chief Resident Association) Chief Resident Meeting in March 2024, about 40 current and incoming chief residents convened to discuss two key questions: “Why are there so few female leaders?” and “What actions are necessary to foster gender-diverse leadership?” To encourage candid feedback, an anonymous online polling system was utilized. Table 1 presents a categorization of audience responses. Results highlighted key challenges such as work-life balance struggles and inadequate leadership training. Many participants emphasized the unequal distribution of clinical and administrative workloads among female leaders. This letter presents insights from the discussion and potential solutions to advance gender equity.</p><p>Participants noted that traits such as modesty and humility, often associated with women, contribute to their hesitation in assuming leadership roles. The “imposter phenomenon,” characterized by a tendency to underestimate one's abilities, was also frequently mentioned.<span><sup>3</sup></span> These observations underscore deep-rooted biases affecting leadership perceptions and career advancement.</p><p>The physical demands on women and their career impact were recurring themes. Mid-career breaks due to childbirth and childcare responsibilities pose major obstacles, affecting promotion opportunities. Matsui et al. found that female medical students prioritize family-career balance when making career choices, whereas male students focus on work initially and adjust later.<span><sup>4</sup></span>