Often called “the most difficult job in the world”, the Secretary-General of the United Nations must fulfill a difficult role as both world moderator and chief administrator within the organization. For the last seventy years, those selected for this role have done their part to ensure that the United Nations is capable of confronting and solving the world's most important and complex issues. It is, however, unclear that those chosen to be the de facto spokesperson for the United Nations are truly the best choice to fill such an important position. The role of UN Secretary-General has expanded dramatically in the decades since it was created, but the election of such a crucial leader has remained the same. This paper is broken into two sections. The first, introductory section details the creation of the selection process as set forth in the 1945 United Nations Charter, and the historical and present realities of the influences of the Security Council and General Assembly on the selection of the UNSG. The second section discusses principles by which reforms to the selection process may be evaluated, and assesses commonly-proposed reforms based on these principles. Emphasis is placed on reforms that reflect best practices of other international organization leader selection, add legitimacy to the United Nations, and can be feasibly implemented. The proposed reforms are drawn both from existing practices in other international organizations and from proposals put forth by non-governmental organizations.