Six major areas considered most likely to present stern challenges to educational leaders in the final years of the 20th century are: (1) changing demographics, (2) economics, (3) technology, (4) occupational and vocational education, (5) human rights, and (6) family structure. Relying on major reports, current periodicals, and personal experiences, the authors of this monograph identify key information about the six areas and stress the extent to which each area is and will be a challenge to educational leaders. The challenges are first described from a general perspective in each of the six areas and then linked to the urban school district of Milwaukee (Wisconsin). (MLF)