The Army must develop strategic leaders who can excel in a future operating environment marked by complexity and uncertainty. The questions becomes, is the Army developing officers that are prepared to serve as future strategic leaders? Unfortunately, operational demands placed on the military since 2001 created a culture that precludes this from happening. This culture rewards tactical experiences over the pursuit of broadening assignments and shaped a cohort of senior leaders that mentor subordinates to maximize time at the tactical level. These issues, combined with limited opportunities in an officer’s career timeline to pursue broadening assignments, created a miss-alignment between the Army Officer Professional Development Program and career management system. This research paper highlights those issues that led to this misalignment, offer recommendations that will alter the Army’s culture, change mentors attitudes, and increase time in an officer’s career timeline to pursue broadening opportunities. The application of these recommendations will realign these programs and lead to the development of diverse strategic leaders able to lead the Army into the twenty-first century.