Conditions of the principalship that contribute to short-term planning are examined in this report, which also offers strategies for longer range educational integrity. A multiple case study approach was used to explore the experiences of 12 high school principals in 5 states. Over 200 interviews were conducted with principals, teachers, staff, and community members. Major characteristics of the principal's job emerged from the data: brevity, variety, interruption, uncertainty, and fragmentation. Suggested solutions include provision of meaningful internships that incorporate elements of uncertainty and fragmentation, delegation of responsibility, and time management. The recommendation is made for local districts' development of a training package that is comprehensive, flexible, and realistic, providing reflective evaluation and continuous support. Appendices list principals' characteristics and issues identified by them as important. (16 references) (LMI)