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This article makes a contribution to interviewing methodology by introducing the iterated questioning approach (IQA). This interviewing technique strengthens the interviewer’s methodological arsenal by exploiting insights from Symbolic Interactionism, particularly Goffman’s concepts of frontstage and backstage. IQA consists of sequenced iterations of a central research question to elicit multiple forms of talk. The four steps are: 1) the baseline iterated question, 2) eliciting frontstage talk, 3) going backstage, and 4) eliciting backstage talk. To show how these techniques can be fruitfully used with different groups of respondents, we reproduce excerpts from our own interviews with two very different populations: disadvantaged high school students and business professionals. We show how the iterated questioning approach yielded both frontstage and backstage talk with the two groups of interviewees. Subsequently, we review the value of the iterated questioning approach as a technique to systematically elicit both frontstage and backstage forms of talk regarding the same identity-relevant themes. Finally, we conclude the article by discussing how the iterated questioning approach can invigorate future interview-based sociological inquiry.