The authors surveyed a group of distinguished clinical teachers regarding episodes of failure that had subsequently led to improvements in their teaching. Specifically, they examined how these teachers had used reflection on failed approaches as a tool for experiential learning. The respondents believed that failures were as important as successes in learning to be a good teacher. Using qualitative content analysis of the respondents' comments, the authors identified eight common types of failure associated with each of the three phases of teaching: planning, teaching, and reflection. Common failures associated with the planning stage were misjudging learners, lack of preparation, presenting too much content, lack of purpose, and difficulties with audiovisuals. The primary failure associated with actual teaching was inflexibly using a single teaching method. In the reflection phase, respondents said they most often realized that they had made one of two common errors: selecting the wrong teaching strategy or incorrectly implementing a sound strategy. For each identified failure, the respondents made recommendations for improvement. The deliberative process that had guided planning, teaching, and reflecting had helped all of them transform past failures into successes.