Senior Army leaders recognize the Army Civilian workforce as a critical part of the total Army and the need to develop multifaceted civilian leaders similar to military senior leaders. The Army conducted multiple surveys and studies over the last decade and launched a Civilian Workforce Transformation in 2010. Three key structural issues—decentralized management of the Army civilian workforce, lack of civilian employee mobility, and an unbalanced grade structure—will prevent these latest initiatives from achieving the Army’s strategic intent. Analysis of key characteristics of these structural issues and the resulting effects on the Army Civilian Leader development programs, the Civilian Education System (CES) and Senior Enterprise Talent Management (SETM) program, show the futility of the current approach. Recommendations include continuing an evolutionary approach that cannot completely ameliorate the existing structural issues or a revolutionary approach where the Army fundamentally reexamines its Army Civilian leader development approach. Further research is needed on the growth in retired military officers transitioning into civil service at high GS pay grades since significant law changes starting in 1998.