The evaluation of a superintendent is often a stressful, unpleasant experience for both the superintendent and the members of the school board. Typical board trustees have little experience in evaluating CEOs. Worse yet, they are hamstrung by the limitations inherent to their roles. They lack the advantage of a day-to-day working relationship with the superintendent, so they must estimate performance based on school district data and sometimes hearsay from patrons or employees. On the other side of this process is the superintendent, who navigates the top executive position, performing many unheralded tasks necessary for the schools' smooth operation, matters that likely fall off the radar screen of the evaluating board. How frustrating it is to be evaluated by individuals who may be passionate about topics that interest them, yet may not have a full appreciation for the totality of the superintendent's overall work performance. Many superintendent appraisals are generic, contain difficult-to-rate subjective items and lack ongoing communication during the process. The author has produced an organic appraisal system that has eliminated most of the perennial stress and unpleasantness for both the board and the superintendent. The approach he designed several years ago broke age-old evaluation traditions, improved trustee participation and built group trust.