This study informs the design and development of pedagogical agents that can flexibly support self-regulation by calibrating guidance to specific phases and facets of self-regulated learning (SRL) as individuals encounter challenges and develop more sophisticated understandings of the task and content. From a socio-cultural perspective of self-regulation, we examine the transition of self-regulatory control from teacher to graduate student during naturalistic instructional conferences. Three goals included (a) examining teacher-student dialogue about a complex task to see if fading actually occurs, (b) examining whether support and fading of support are calibrated to specific phases of the self-regulatory process at a given point in time, and (c) examining techniques used for scaffolding and fading scaffolding directed toward specific phases and facets (behavioral, cognitive, meta-cognitive and motivational) of the self-regulatory cycle. Findings support a socio-cultural perspective of SLR demonstrating a transition from teacher to student regulation across phases and facets of SRL. The paper concludes with an examination of how our findings can inform the design of computer-based scaffolds that can support SRL.