This experiential session will explore a rational, critical self-reflection process used to facilitate transformative learning through transformative coaching methods during interview-style, one-on-one meetings with undergraduate students. Coaching is a professional field of practice dedicated to inspiring clients to their highest level of potential. In striving for these goals, coaches are trained in skills and competencies that overlap with skills and competencies of educators seeking to encourage and carryout transformative learning with their students, especially through dialogue-based methods. Both transformative learning and coaching prompt for critical reflection while holding a non-judgmental space to explore disorienting dilemmas and encourage meaning-making. Participants in this session will be exposed to coaching essentials, discuss their links to transformative learning, hear about how this has been implemented in one-on-one sessions with students at a university, and access sample narratives of how this interaction plays out. Then attendees will be paired-up to practice the methods described. The session will conclude with whole group discussion about the challenges, benefits, possible areas for implementation, and questions.