Research has indicated that dialogic approaches have desirable effects in education, but it is also well-known that it can be a challenge for teachers to make the transition from the traditional teacher role to that of the facilitator. Based on a case study, this article investigates the successes and shortcomings of 29 teachers learning to facilitate classroom dialogue in teacher development programmes. The article analyses the trainees' written self-evaluations and the supervisors' feedback to examine the extent and nature of the challenges encountered as well as the teachers' self-perceptions compared to the perceptions of the trained supervisors. The main findings were that the teachers encountered many challenges, especially when it came to adopting the role of a facilitator and supporting the students' reasoning and interaction. In addition, their own assessments of their performances were generally unreliable. Nonetheless, with supervised training, the teachers were successful in learning to facilitate philosophical dialogues.