Teachers’ appraisal is key to enhancing their professionalism, which translates to effective curriculum implementation. This paper sought to evaluate the Teachers Performance Appraisal and Development (TPAD) process in Kenya with a view to identifying its challenges and suggesting ways of enhancing it. The study took a philosophical approach, subjecting the teachers’ appraisal process to criticism in light of the Socratic Pedagogical theory. The study established eleven errors that riddle the teachers’ appraisal process. These are the errors of strictness, leniency, central tendency, halo effect, recency of events, failure by participants to identify professional development gaps, failure by participants to attend the appraisal meetings, subjectivity nature of the TPAD appraisal process, alienation of some participants from the appraisal process and passive participation of some participants.The study utilized the six tenets of Socratic Pedagogy (participatory, dialectical, conversational, inquisitive, rational and practical tenets), interpreted to constitute the soul of the TPAD appraisal process, to fix the aforementioned errors. Therefore, the study recommended that the TPAD online system be reconfigured so that the appraisal process could be in tandem with the soul of the appraisal process.