This study focuses on the impact of in-service training (INSET) to practicing teachers in Greece and the possible reasons that might make such training less attractive to them. Observation for development is considered as an alternative to short-term training programs so that teachers can develop a deeper awareness of their teaching context, in close collaboration with their peers. Quantitative and qualitative data were gathered from a questionnaire and a focused interview; seventy respondents participated in the former tool and seventeen in the latter. Findings indicate no fundamental change in the trainees’ beliefs or teaching practice. Theories of teacher training and development are used to explore what teachers expect from training, what the reality of INSET is both for the public and private sectors, and finally how self-reflection and peer-observation can be integrated into teacher education programs to boost teacher learning and development. It is argued that awareness-boosting training programs are essential in order for trainee-teachers to develop their own teaching theories.