Background/Context: Teacher educator development remains an undertaking that is both understudied and underavailable as an explicit professional path, despite scholarship suggesting that teacher education's transformative potential hinges on teacher educators' pedagogical work. Purpose, Practice, & Participants: This article reports on a qualitative study that explored the development of teacher educators who expressed deep commitments to educational equity for minoritized youth. Fifteen current and prospective teacher educators participated over three years in situated adaptations of two critical pedagogical approaches: Freirean culture circles, where participants engaged in critical dialogue around conflicts encountered in their teacher education work that involved issues of inequity, particularly deficit-based ideas of P-12 students and their families, and Boalian theatre (or teatro), interactive role-play where participants dramatically re-enacted these conflicts and imagined potential responses to them. This study examines the ways in which these critical pedagogical spaces facilitated participants' development as asset-oriented teacher educators. Research Design & Data Collection: This research represents an ethnographic self-study, as the authors engaged in culture circles and teatro as participant-researchers. To study these spaces of critical teacher educator development, the authors collected ethnographic data, which included semi-structured interviews with each participant, field notes, and audio/video recordings of dialogue and role-play, as well as participant written reflections. Findings/Results: Through their engagement in culture circles and teatro, participants came to recognize some of the micro-pedagogies of asset-oriented teacher education, grappled with the relational dimensions of teacher learning, became familiar with possible tools of asset-oriented teacher education, and interrogated the social, political, and historical dimensions of the work. In doing so, they understood each area as linked both to specific settings and individuals and as connected to more common dilemmas that may play out across teacher education contexts. Conclusions/Recommendations: While cautioning against widespread, mechanistic implementation, the authors recognize culture circles and teatro as offering special promise for the development of asset-oriented teacher educators. In particular, findings suggest that these critical pedagogies support the conditions for learning--particularly spaces that center participants' identities and experiential conflicts--that can cultivate complex understandings about, and tools for engaging, the contingent work of asset-oriented teacher education. Such spaces seem particularly well equipped to cultivate critical understandings deemed essential for transforming the field of teacher education.