A facilitator is commonly defined as a substantively neutral person who manages the group process in order to help groups achieve identified goals or purposes. However, outdoor educators rarely experience the luxury of only managing the group process, because they are typically responsible for the provision of leadership, skill instruction, and safety management. Based on personal experience, the literature on facilitation, and my research on the theories and practices of facilitator educators providing facilitation training courses in Australia and New Zealand, I recommend strategies for managing the potentially conflicting facilitation roles that outdoor educators may be required to fulfill. The five facilitator roles identified by Schwarz (2002), which serve as a theoretical framework for this paper, are facilitator, facilitative leader, facilitative trainer, facilitative consultant, and facilitative coach. The similarities and differences between these roles are discussed, as are strategies that outdoor educators can apply to optimise their use of, and movement between, these roles.