It's strange your special education training didn't tech you the basics of behavioral psychology. If I as a dog trainer were in this position, I'd ask myself what smaller pieces of the task I could teach the person so that they incrementally can take on more. I also would concentrate most on the final/finishing bits of the task first, so that the person is confident with the last piece and then add the previous step, etc. This allows the person to go from the new skill that they're not that confident in to a skill they have more experience with and are more confident in. Behaviorists call this back chaining. Think less like a manager and more like a teacher/trainer.