A single subject alternating treatment design was used to compare most-to-least and least-to-most prompts to teach work tasks in community businesses. Four students with moderate to severe disabilities, two paraprofessionals, and one transition teacher participated in the study. Results of the study suggest that both prompting strategies were effective in promoting the acquisition and maintenance of employment skills taught in community employment training settings. The special education teacher and paraprofessionals implemented the prompting strategies with fidelity and minimal training. Results are discussed in terms of future research and implications for expanding the scope of community-based employment skills training.