Critiques of Masters in Business Administration strategic management education have centered on the failure to adequately integrate two core orientations of the strategic management process, that is, analysis and implementation. Thus, attempts to measure assurance of learning in strategic management capstone courses will inevitably reveal gaps in the degree of deep learning that has occurred in a business program. In this article, we argue that a linear or serial approach to case analysis is a prime culprit in contributing to weaknesses in deep learning and critical thinking. This approach encourages weak reflections, lack of innovation in generating strategic options, and poor implementation planning. We analyze various contemporary approaches to strategic management education in relation to deep learning outcomes and, relying on Bloom’s taxonomy, we propose an alternate, reflection-based framework for teaching strategic management culminating in a discussion on its implications for teaching and practice.