Digital transformation is one of the key challenges facing contemporary businesses. The need to leverage digital technology to develop and implement new business models forces firms to reevaluate existing capabilities, structures, and culture in order to identify what technologies are relevant and how they will be enacted in organizational processes and business offerings. More often than not, these profound changes require firms to revisit old truths as they develop strategies that thread the needle between beneficial innovation and harmful disruption. This article uses the Internet of Things (IoT) as a backdrop to demonstrate the concerns associated with transformative technologies and offers five recommendations as to how firms can develop the strategies needed for digital transformation and become digitally conscious: (1) Start small and build on firsthand benefits; (2) team up and create competitive advantage from brand recognition; (3) engage in standardization efforts; (4) take responsibility for data ownership and ethics; and (5) own the change and ensure organization-wide commitment. As such, this article shows that digital transformation should be a top management priority and a defining trait of corporate business strategy, and that by becoming digitally conscious, firms may get a head start on their transformation journey.