Building effective school-to-work systems requires evaluation, usually incorporating both process and outcome evaluations. Increasingly, school-to-work systems are conducting self-evaluations or hiring evaluation teams to determine how effectively the system is designed and implemented and whether it is achieving its purposes for students and the community. Favorable evaluation results can be used for marketing the school-to-work system. Designing an evaluation of a school-to-work system requires the following steps: (1) identify stakeholders; (2) define the evaluation's purposes; (3) clarify goals and objectives; (4) determine evaluation roles and hire an evaluator; (5) write measurable evaluation questions; (6) choose evaluation methods; and (7) design recordkeeping procedures. Examples of effective practices of evaluation of school-to-work programs have been identified in Oregon State's Youth Transition Program and the Milwaukee Public School System. (Contains 10 references and an annotated list of 13 organizations are included in the report. A one-page fact sheet describes funding of the school-to-work system.) (KC)