Formed in 1987 as part of the Cardinal's civic agenda, Challenge to Leadership (CTL) was a forum and network of business, church, community, labor and education leaders to promote regional collaboration on issues that were common to all and where action was critically needed. In 1990 the CTL released The Volunteer Challenge: An Inventory of Volunteer Needs and Resources in Greater Boston and in 1991 CTL published the Massachusetts Educational Inventory, which helped lead to the Massachusetts Educational Reform Act. The following year CTL assembled over fifty corporations and government agencies to engage in an effort led by Michael E. Porter of the Harvard Business School to address the Massachusetts economic recession of the early 90's. In 1992 the CTL issued Toward a Shared Economic Vision for Massachusetts in collaboration with Porter, which a leading business journal called the best business plan in America.
In 1995 working with James Fox at Northeastern University and the Ten Point Coalition, CTL released Toward a Safer and Less Violent Community. The effort resulted in the community-policing plan in Boston that was recognized as a national model. Although the CTL disbanded in 1997 when it became clear that increasing success required more than a volunteer organization to serve the continuing need for regional collaboration, its efforts in the area of education, economics and public safety are well embedded in Massachusetts public policy today.