Throwing the proverbial monkey wrench into the machinery "on paper" before a system begins functioning seems to be essential to program evaluation. This activity should be performed by the "resident skeptic" who is familiar with past resistance to change and who, being familiar with a program, is able to foresee theoretical and practical problems. Such creative pessimism should be applied to the evaluation of Title One Programs in a large urban district. It may prove useful to categorize anticipated concerns and potential problems under six general headings: (1) Planning: includes providing useful data within a mandated time frame and specification by the Federal Government of minimum evaluation requirements, (2) Organization: includes setting up an organizational linkage between the evaluation and instructional arms of a school system, (3) Implementation: includes considering evaluation results in program and management decisions and combating outside criticism that research and evaluation activities constitute a frill, (4) Dissemination: includes avoiding gross oversimplification of research results, (5) Personnel: includes convincing personnel that program evaluation should not be equated with personnel appraisal and (6) Miscellaneous: includes addressing demands for non-existent information, adjusting to the Buckley amendment and contracting with outside firms for evaluation services. (Author/BJG)