Students in the 21st century management information systems (MIS) classroom are seeking not only conceptual understanding but also methods of communicating that are familiar and accurately reflect how they learn and acquire knowledge. Concurrently, employers of 21st century job applicants are still looking for many of the same skills they sought more than a decade ago. As a result, teachers are tasked with curricular planning that involves a delicate balance between content, resources, tools, and environmental demand. In this paper, the authors propose a modification to a well-established course design framework -- Understanding by Design® -- as a solution to combining MIS content and sought-after soft skills with social media tools and resources favored by the current college-aged population: digital pioneers and natives of Generations Y and Z.