In the simplest of terms, leadership/management success is measured by an individual's ability to meet the expectations of the person who is responsible for the evaluation. The greater the level of responsibility, the more complex the evaluation process becomes and the more grounded the expectations are in specific performance indicators (Superintendent's goals may be made public). Superintendents conduct the process with their executive cabinet, who in turn conduct the process with their team, and so on.
Superintendents are the only school district employee not supervised or evaluated by another credentialed professional. The superintendent evaluation process is in itself an entirely different animal. Among the greatest challenges of superintendent evaluations is ensuring the school board, micro-political factors aside, is appropriately prepared and trained to honor both the intent and spirit of the evaluation process.
Every element related to job performance should be aligned (e.g. resume, entry plan, evaluation). For example, a resume should provide demonstrated evidenced that the person has met or exceeded the expectations of their current position (as evidenced by successful evaluations) and as a result is qualified for a position of increased responsibility. The expectations of the new position, then, become operationalized in a new set of performance indicators and memorialized annually in an evaluation, which in turn would become evidence that the person has met or exceeded expectations for the new position, in an endless cycle. An entry plan is used to identify one set of performance indicators that the evaluatee considers critical to their success.
Evaluations are not events. Taking the evaluation process seriously and engaging at the deepest and most sophisticated level prepares leaders for the complexities of future positions of increased responsibilities. It begins with sound practices that meet the standards of propriety, utility, feasibility, and accuracy. Evaluations in education as a whole have not earned praise for bringing value to an organization. It starts at the top of the pyramid. When school boards and superintendents engage gainfully in the process it becomes the culture of the organization. Learn more about performance management below in a series of essays I've written on the topic. Also, see the collaboratively and recently developed performance management system and toolbox currently in practice in my district by clicking on the image.
"All too often superintendent evaluations are performed hurriedly in an attempt to satisfy a legal requirement or a policy mandate. If the evaluation is merely an event it has little, if any, impact on the professional growth of the superintendent or improvement of the school district. The success of the superintendent and, ultimately, the success of the school system are inextricably tied. If the superintendent of schools is to receive a fair evaluation, and if the evaluation is to contribute to her or his professional development, success and overall effectiveness of the district, then adequate time and resources must be devoted to designing, developing and implementing a comprehensive and quality performance evaluation system."
Michael F. DiPaola