A teachers’ training project, employing teacher-mentored in-school training approach, has been recently initiated in Greek secondary education for the introduction of Information and Communication Technology (ICT) into the classroom. Data resulting from this project indicate that although teachers express considerable interest in learning how to use technology they need consistent support and extensive training in order to consider themselves able for integrating it into their instructional practice. Teachers are interested in using ICT (a) to attain a better professional profile, and (b) to take advantage of any possible learning benefits offered by ICT but always in the context of the school culture. They are willing to explore open and communicative modes of ICT based teaching whenever school objectives permit, otherwise they appear to cautiously adapt the use of ICT to the traditional teacher-centered mode of teaching (strongly connected to the established student examination system). Teachers’ attitude to adapt ICT mode of use is supported by research evidence that emphasize the situational character of knowledge and expertise. Authors employ a model premised on Perceptual Control Theory to interpret available data and discuss the view that introducing ICT into schools can be understood as a “negotiation” process between cultures.