Growing complexity and diversity of strategic decisions indicate the need for applying the appropriate holistic tools in strategic decision making. Thus, the chapter deals with the process of strategic decision making from the viewpoint of critical systems thinking, with emphasis on the role of values and context in strategic decision making. The main purpose is to show how systems thinking generally and critical systems thinking particularly can help decision makers involve different perceptions and values in the process of strategic decision making, as well as take into account context in which the strategic decisions are made. Considering the key internal and external factors affecting strategic decision making, the authors have selected three systems methodologies stemming from different paradigms: soft systems methodology as interpretive, team syntegrity as emancipatory, and organizational cybernetics as functionalist systems methodology. The way in which they can be combined, aimed at improving effectiveness of strategic decision making, has been presented.