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This paper discusses findings from case study research of four secondary schools in Michigan as they implement the Reading Apprenticeship (RA) literacy initiative across two years. The author extends past research (Cohen et al., 2013), which discusses the “puzzles” that reformers face when attempting design-based, large-scale school improvement. Using qualitative data from these cases, the author proposes that the dilemmas with which reformers are faced trickle down to the school. The work of design, implementation, improvement, and sustainability is interactive, ongoing, and elicits problems with which school actors must continually grapple. The author concludes by exploring the implications of this iterative work being done at a level and during an implementation phase that is often assumed to be more fixed.