Data-driven decision making has now moved beyond its traditional domains—operations research, business economics, computer sciences, and business statistics—to “softer subjects,” such as human resource management, organization behavior, and business communication. In this context, teaching with technology encourages students to systematically apply domain knowledge to communicate across a wide variety of stakeholders. In the era of multimodal forms of communication and multiple data sources, management students must be analytical when writing compelling reports and giving persuasive presentations. They should be well versed in using both quantitative and qualitative techniques for report writing and presentation. Drawing on authentic user-generated comments on social media, this article presents two case studies on (a) crisis communication by 30 CEOs and (b) culture shock experienced by foreign tourists sojourning in India, China, and the United Arab Emirates, to demonstrate how master’s in business administration (MBA) students could derive insights from the online comments to make strategic decisions for organizational benefit and make reports based on those findings. The article asserts that this could help to cultivate a data-analytic mindset among the students by preparing them to communicate small (and big) data-driven analysis to relevant stakeholders. It attempts to suggest ways to develop MBA students’ ability to analyze their potential audiences as well as to generate meaningful insights from the available information on social media websites. Finally, it hopes to nudge business communication instructors to embrace multidisciplinary perspectives for planning a technology-based business communication assignment involving the social media landscape. Instructors can not only use the two case studies to illustrate ways to integrate technology with teaching but also create their own mini cases to improve the decision-making, report-writing, and business report presentation skills of their students.