Common technical problems can overwhelm managers who lack basic technical experience. Many managers eschew technology projects due to their self-efficacy, or intrinsic beliefs about their ability to successfully solve specific tasks. Competitive organizations require managers who can not only take charge of problem situations involving technology without wasting limited resources, but also leverage those resources in a manner that enhances organizational learning and reinforces knowledge management. The authors present an iterative model as a starting point for analyzing such problems. The model recognizes business competencies as a foundation for acquiring technical knowledge by examining situations through the four, iterative lenses of Objectives, Technology, Implementation, and Support (OTIS), thereby increasing the managers’ organizational value, marketability, and career opportunities.