Using an empirical research study based on a systematic sample of teachers, school counselors, and principals working in Slovenian primary and secondary schools, we examined how frequently these education professionals self-evaluate their work. The multiple regression models demonstrated that educators’ interest in research work and belief in the necessity of continuous professional development have the strongest impact on their views of the importance of self-evaluation. Those educators whose knowledge of conducting self-evaluation is greater also attach more importance to carrying out self-evaluation. School management’s encouragement has a further impact on educators’ views on the importance of conducting self-evaluation. If an educational institution is to adopt self-evaluation as a permanent expert activity, which is a precondition for effective quality improvement, it needs to develop an adequate atmosphere among its educators. This atmosphere should enable and encourage research work, self-evaluation, and educators’ professional development.