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In the setting of a writing center tutoring world where calibrated questioning is typically a core strategy of connecting with, evaluating, and ultimately counseling student writers, my work is an attempt to discover by examination and evaluation the effectiveness of questioning tools and techniques used by writing tutors and teachers. My purpose is to offer potential refinements to common questioning methods so as to help tutors better facilitate student writers in generating their own solutions to writing quandaries, as opposed to being led to preconceived tutor-generated solutions. The content of this paper is based upon my observations of tutoring sessions conducted by experienced tutors in the Utah State University Writing Center and my own experiences as a writing center tutor as informed by the recommended questioning strategies of The New Bedford Guide for Writing Tutors and supplemental readings of educational theorist Paulo Freire, and FBI Chief Negotiator, Christopher Voss. Ultimately this paper concludes that though tutors and teachers often use open ended questions, they use them in sequences of leading questions, the result of which is the transformation of seemingly open-ended questions into highly constrictive questions.