This dissertation contributes to the strategic cognition research by exploring how managers’ cognitive representations of an emerging, but potentially disruptive technology, influence their identification of strategic options. Managers tend to talk of social media as technology that changes customer behavior and disrupts industries, however, this attitude is not reflected in their strategic framing and implementation of social media. As behavioral theory seems inadequate to account for such paradox of social media sensemaking, two qualitative studies purposefully account for the sociocognitive challenges of understanding and using new, disruptive technology in business-customer interaction and provide theoretical frameworks for overcoming barriers to business transformation in the digital age. Departing from a thorough review within the marketing and business management disciplines, the studies illustrate how managers’ strategic perspective is delimited, at the subconscious level, by experience, knowledge, and assumptions of businesscustomer interaction, market dynamics, and social media acumen, and how these biases are often confirmed in a social context instead of being challenged, despite of a market-driven, as well as an organizational demand of rethinking. Elicitation of the underlying conceptual structures of social media is based on in-depth interviews with 39 strategic decision-makers on B2C markets in Europe and the US. The first study across companies empirically investigates how strategic decision-makers cognize, formulate, and implement social media differently, and how managers’ cognitive understandings of social media are acquired. A detailed study within a media company further demonstrates how managers’ identified strategic framings of social media can express different operations of conceptual change of strategies through reflective thinking as higher-order learning. These framing operations can be the basis for discovering possible reorganizations of strategies (strategic reframing) to become aware of new opportunities with social media. The identification of the conceptual structures underlying managers’ strategic cognition of social media through mental models and framing mechanisms contributes to the discussion of how strategic cognition of social media can strengthen the development of business and customer value, as well as individual and organizational capabilities. The findings lead to more nuanced understandings of the microfoundations of strategy at the intersected levels of management, cognition, market, and media. To my knowledge, this is the first attempt to comprehensively capture the variety of conceptual representations of social media at managerial level, and to theoretically and empirically account for how these socio-cognitive operations underpin a strategic change process involving social media at organizational level. The findings suggest how reflective thinking - at individual and collective levels - can help strategists and companies to better meet future challenges of adopting new technologies. The ability to challenge own and others’ assumptions through reflective thinking can be initiated through reframing techniques and models developed from this research. Such practices become important to establish when businesses become increasingly dependent on fast-moving technology. Strategic processing becomes a critical precondition for understanding the nature of change and transformation and to be able to relate to customers in an appropriate manner.