The leadership philosophy of Mission Command has been identified by the Chairman of the Joint Chiefs of Staff as a critical enabler to the implementation of Joint Force 2020. Technological advances in information distribution, manifested in the internet and the 24-hour news media, and network connectivity, manifested in the development of a network-enabled force, have significantly challenged the effective implementation of Mission Command. These Information Age challenges have provided operational commanders the motive and the means to micromanage their forces and move away from the decentralized execution espoused by Mission Command. Operational commanders must possess specific leadership traits in order to overcome these challenges, the two most important being boldness and interpersonal communication skills. The criticality of these leadership traits will be proven through an analysis of the principles of Mission Command, the nature of the Information Age challenges, the characteristics of the identified leadership traits, and historical examples. By recognizing the significance of these leadership traits, appropriate measures can be taken to ensure their development in our current and future leaders.