Becoming an experiential educator involves more than just being a facilitator or matching learning style with teaching style. Experiential education is a complex relational process that involves balancing attention to the learner and to the subject matter while also balancing reflection on the deep meaning of ideas with the skill of applying them. A dynamic matching model for “teaching around the learning cycle” describes four roles that educators can adopt to do so—facilitator, subject expert, standard-setter/evaluator and coach. A self-assessment instrument called the Educator Role Profile was created to help educators understand their use of these roles. Research using the instrument indicates that to some extent educators do tend to teach the way they learn, finding that those with concrete learning styles are more learner-centered, preferring the facilitator role; while those with abstract learning styles are more subject-centered preferring the expert and evaluator roles. A model for the practice of dynamic matching is presented.