Taking on the role of literacy coach can be a daunting task for even seasoned educators. In this article, the author examines her experiences in this role as work for a university class she was taking. In a sense, she "tries on" the coaching role in order to discover if it is a job she would truly be willing to take. She discusses the difficulties facing coaches as they go into classrooms to observe as well as her successes and failures in holding conferences with those teachers who allowed her to observe in their classrooms.