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Mentoring has the potential to positively impact teaching and learning, yet too often falls short in schools impacted by systemic inequities. “Educative mentoring,” which can occur “inside” or “outside” of the action of teaching, re-orients mentoring towards rigorous teaching and learning. A majority of mentoring occurs “outside” suggesting “inside” practices, which potentially expedite teacher/student growth, are underutilized. Niceness, a shared disposition, works to keep interactions pleasant, often protecting educators from meaningfully challenging biases and inequitable systems and practices. This cross case analysis of two experienced educative mentors’ in Title 1 schools explores if/how operationalized niceness leads well-meaning mentors to avoid conversations/actions that facilitate meaningful teacher growth but also creates discomfort.