During a time of accelerated change and automation, leadership in the shipping industry emerges as a much-needed competence pertaining to the survival and safety of crew on board, as well as to the growth of shipping companies. Despite many years of leadership research, our knowledge on how to develop and apply leadership skills in shipping remains limited, focusing on rather autocratic-oriented leadership styles, similar to those found traditionally in the armed forces. The present paper aims to analyze the key aspects of traditional leadership theories and of military leadership practices, and to further examine their applicability to the modern shipping industry. Towards this end, a systematic literature review in the area of leadership in the armed forces, with emphasis on the navy, and merchant shipping is conducted, whereby challenges and best practices are identified. The literature survey reveals that there are similarities in the role of hierarchy between the navy and merchant shipping. The navy promotes leadership behaviors that diverge from the traditional leader–follower model. Such practices can be useful in the context of commercial shipping in order to inspire leadership behaviors that promote and support the creation of self-efficient and emotionally engaged followers. Maritime Education and Training institutions could benefit from the findings of this research and enrich their curricula with educational material that will equip future leaders with the necessary skillset.