This study examined dynamic decision-making processes at three different levels in the field of instructional design (ID): (a) for managers of instructional designers (IDers) at the institutional level, (b) for Senior IDers at the program level, and (c) for IDers at the course level. This qualitative study utilized collaborative autoethnography (CAE) to address a gap in the literature by explaining ID decision-making processes provided by three professionals at three different levels: institutional, program, and course. This study followed the framework for the dynamic decision-making process by Stefaniak et al. (2022) to examine how each level approaches: (a) conjecture within bounded rationality, (b) exploring through analogical reasoning, and (c) design-in-action. The researchers identified three themes through thematic analysis in their reflections: bounded rationality across three levels, strategies for analogical reasoning across three levels, and design-in-action strategies across three levels.