The establishment of the homeland security enterprise within the United States created new challenges for executive decision makers at the federal, state and local levels of government. In the second decade of the 21st century, matters of homeland security and national security seemingly grow closer to one another, as transnational threats abroad increasingly influence events at home. Executive decision makers at all levels of government face significant challenges, often under the pressures and constraints of crisis conditions. Public leaders need not face significant decisions alone and in a vacuum, devoid of subject matter expertise and guidance. The role of advisors in supporting public leaders is broad and underexplored, particularly in the evolving homeland security space. In this Viewpoints video, Theodore Berger, Chief of Staff for the City of Chicago Office of Emergency Management and Communications, discusses his Master’s thesis, which examined the relationship between advisors who support executive decision-makers in the homeland security enterprise and national security domain and the factors that influence the advice process. This thesis seeks to tie the experiences of high ranking practitioners with the viewpoints of academics in social science to derive a better understanding of what leads to success as an advisor.