The purpose of this article is to present a single case study about a newly graduated speech-language pathologist working in a small, urban school district and her experiences with a series of speech-language assistants having various levels of qualification and personality types. The case illustrates how levels of professional supervision skills, pre-service paraprofessional training, professional/paraprofessional role distinctions, hiring practices, pay, and working conditions interact and impact on the successful use of speech-language paraprofessionals working in education settings. Evidence gathered in the case support the contention that pre-service preparation for speech-language pathologists to function in supervisory roles is an important factor in ensuring the appropriate use of speech-language paraprofessionals.