This paper responds to Ippolito et al.'s (2021) "wonder," "What preparation and in-service support do coaches need to become systems thinkers, thought leaders, and change agents within their schools" (p. 182) by describing the obstacles and complexities experienced by two first-year literacy coaches as they transitioned from classroom teacher to coach. They described challenges related to adult learning principles and communication (e.g., questioning) and understanding their role and position when working with teachers. Ultimately, they wanted to feel valuable to teachers but did not know what that looked like. The findings from this paper highlight the need for specific training in negotiating roles within relationships and adult learning principles. Coaches must understand adult-centered communication and receive ongoing professional learning to develop a repertoire of adult communication strategies that will help them work with a broad swath of teachers.