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Starting a new leadership or mentoring role is a daunting task that comes with a host of new responsibilities and expectations. With the question, "In what ways does participating in the mentoring process help facilitate changes in the Self?" this study explored our identities as leaders and followers through the Dialogical Self Theory (DST) lens. We utilized each other as critical friends to unpack our leadership dilemmas to explore the complexity, uncertainty, and fluidity of identity. What emerged were the dynamics of a coalition of positions, the role of individual and group dialogue, and its significance in realizing the ongoing reconstruction of our identities and our roles as mentors.