The purpose of this paper is to explore the predicaments and improving strategies of the instructional supervision system in Taiwan for the new century. There are three parts to this paper. Firstly, the concept of instructional supervision is analyzed. Secondly, the predicaments of the instructional supervision system in Taiwan are examined, which include instructional supervision as not clearly defined, the appointment of instructional supervisors is not sound, the professional knowledge of the instructional supervisors needs to be enhanced, and the function of instructional supervision system is not manifest. Finally, the improving strategies to the predicaments of the instructional supervision system are proposed, which comprise of a clear definition of instructional supervision, the professionalization of instructional supervisors, and the application of the function of instructional supervision.