In many companies the process of new Information Technology (IT) identification and assessment lacks the rigor associated with experimentation. The realities of maintaining daily operations and the expense and expertise involved distract firms from conducting experiments. The authors explore cases of how companies introduce a new IT for the business use of digital social media. Because social media technologies are new, interest in its use is broad and diffused leading organizations to be unsure about how best to implement social media, prompting organizations to follow a mindful process of experimenting with these technologies. The cases illustrate that the extent of mindfulness influences how new technology implementations are introduced, supporting wider boundaries in assessments, richer interpretations of the IT's usefulness, multi-level foci concerning benefits and costs, persistence to continue exploration, and a greater use of fact-based decision-making. The authors observe that following a mindful introduction process reaps some of the benefits of experimentation, such as greater stakeholder satisfaction and organization-wide learning and understanding of the technology's potential.