In this paper, we offer a conversation between researcher and music educator on the experience of engaging in a participatory philosophical inquiry methodology. This grounded methodology builds upon new trends in the philosophy of education that shift away from high-order normative theorizing, beginning instead with the ethical dilemmas teachers face in their classrooms (Levinson & Fay, 2016, 2019; Morton, 2019a; Santoro, 2018). This participatory philosophical inquiry was developed to explore the normative tensions that arise between teachers’ pedagogical authority and their pursuit of multiple, sometimes competing, democratic educational aims, particularly in the context of school wind bands. The methodology comprised three stages. First, qualitative interviews generated first-hand accounts of teachers’ experiences and perspectives as musical and pedagogical authorities. The second stage involved the co-creation of a normative case study (Levinson & Fay, 2016, 2019) from participants’ experiences to articulate the principal values at stake when teachers attempt to balance their authority with democratic classroom practices. Finally, the case study was discussed in a Community of Inquiry (Golding, 2015; Gregory & Laverty, 2018) in order to reconsider theoretical views of authority presented in the researcher’s initial conceptual frameworks as well as in the teachers’ earlier reflections. Throughout each phase, teachers’ perspectives were analyzed recursively, with participants, to understand how they align with—or come into tension with—conceptual frameworks of democratic pedagogical authority.From the researcher’s perspective, this collaborative philosophical analysis complicated and disrupted common binaries in contemporary music education theory—binaries that suggest conductors’ pedagogical authority inevitably reflects and reinforces larger anti-democratic patterns of social hierarchy and inequality reproduction (Allsup & Benedict, 2008; Gould, 2008; Philpott & Wright, 2012; Schmidt, 2005; Wright, 2016). Instead, our discussions revealed a nuanced, relational, and social picture of pedagogical authority that is potentially congruent both with the authority of expertise, as well as the development of students’ democratic autonomy and agency. From the educator’s perspective, engaging in this inquiry helped unsettle long-held perceptions of authority, offering perspective and practical tools to ask better questions of my own teaching: When do I guide? When do I step back? This nuance continues to reshape my classroom toward more relational, democratic practice.The reality of navigating tradeoffs between one’s expert authority as educator and musician and the promotion of students’ democratic agency is profoundly complex. In this dialogue, we discuss how the participatory philosophical inquiry challenged our preconceived understandings of this relationship and underscore the value of normative tools in helping teachers clarify the goods to which they aspire, the means to get there, and the potential losses accrued in the process.