According to the United States Census Bureau, approximately 3.1 million high school students have part time jobs. However, little is known about how youth use communication tools in professional work environments. In this paper, we present preliminary findings from an investigation into how youth employed in a 3D print shop use Slack, a popular workplace communication tool. We focus on qualitative data collected during the print shop’s first year of operation. We provide insight into some of the challenges faced by youth employees while configuring Slack on their devices, and some of the ways that youth needed to adapt into being proactive and responsive in the workspace. These early findings suggest that despite being digital natives with prior experience communicating online, transitioning to Slack was not an entirely natural process. These findings will be used to inform a deeper investigation into the usage of Slack by youth working in technical jobs.