Undergoing education reform, the educational system of Cyprus seems to be seeking ways to shift teacher evaluation from a practice that stagnates teacher motivation to a practice that would raise, develop, and sustain teacher motivation towards teacher effectiveness. Teacher effectiveness may develop through formative teacher assessment, which can motivate teachers to generate outputs, namely student learning outcomes, and contribute to the improvement of the quality of the provided education. Being inspired by a conceptualization over the content of two qualitative research studies, which, in the context of secondary education of Cyprus, investigated teacher motivation and teacher evaluation respectively, this chapter recommends a goal setting, interactive teacher-teacher school-based evaluation practice of a formative type, which, being conversational and, therefore, motivational, may lead to teacher effectiveness.