The “leaky pipeline” concept in surgery refers to the phenomenon of losing capable individuals at various stages of surgical training due to systemic structural barriers and workplace culture. Despite growing numbers of women entering medical schools, the pipeline to surgical leadership remains predominantly male-dominated. Sexual harassment, bullying, and discrimination against women are pervasive, making it difficult for female surgeons to thrive. Moreover, surgical training is notoriously inflexible, with long working hours and high demands on personal time, disproportionately affecting women. In response, Women in Surgery network and the Women in ENT group have been established to provide mentorship opportunities, access to networking events and educational resources, and create a more inclusive and equitable workplace culture. The Royal College of Surgeons of England has commissioned the Kennedy report on diversity in surgery, which includes recommendations addressing the attrition of women in surgery. These initiatives have led to a rise in female ENT surgeons over the last decade, with an increase in female ENT surgical trainees from 32% to approximately 48%, and growth among women serving as ENT consultants, increasing from 10% to 18%. While the progress made by these initiatives towards increasing gender diversity in surgery is commendable, progress has been slow, and more comprehensive and multifaceted approaches are needed. The article argues that active participation of all stakeholders, including the Colleges, organizations responsible for surgical training, and surgeons is required to change this culture and fix the leaky pipeline.