Several studies have shown the complexities that teachers faced when planning for instruction in technology enhanced learning environments (TELE). Although classroom-oriented instructional development (ID) models have the potential to help teachers think and plan for effective instruction with technology, teachers are often reluctant to use these models. This article aims to formulate a set of guidelines that will be adopted by teachers for instructional planning in TELE. By examining three existing ID models (Reiser & Dick, 1996; Morrison, Ross, & Kemp, 2004; Smaldino, Russell, Heinich, & Molenda, 2005) through the activity theoretical lens, five guidelines are formulated for mediating instructional planning in TELE: (1) adopt a nonlinear and non-sequential treatment of ID elements; (2) account for decisions made by other participants; (3) recognize teachers' interactions with their instructional and sociocultural-historical contexts; (4) facilitate teachers' re-examination of their existing practices to identify contradictions in his/her instructional planning process; and (5) support teachers' formulation of solutions to the contradictions and employment of transformed practices for effective instruction. (Contains 4 figures.)