Professional development programs (PDP) are an important tool for achieving educational goals; assessing their effectiveness, however, is complex. The success of PDP depends on teachers' ability to transfer newly gained knowledge and skills into practice. To assess this effectiveness, it is necessary to develop appropriate methodological tools. The goals of this study were to develop and apply a methodology for assessing the development of near and far transfer skills among participants in an in-service teacher training program for educators working with youth at risk. Interviews with 114 educators were used to assess near transfer based on a three-level scale: naive, awareness, and mastery. Performance tests that included educational dilemmas were used to assess far transfer skill among 554 educators. The development of transfer skills was examined according to the seniority of the PDP participants. Research results indicated that the training program had a positive effect on near transfer skill but was less effective on far transfer skill. The paper provides tools to assess the development of transfer skills for continual improvement of PDP.