Design professionals utilize numerous design tools that offer hundreds of features through their interfaces to design complex artifacts. In this work, we aimed to understand how design professionals learn software features and seek help on-the-job in today’s modern workplace of interconnected spaces and increased access to shared online learning resources and knowledge management tools. We conducted 20 interviews with design professionals working in different disciplines such as architecture and planning, construction, structural design, and broadcast media, who used complex feature-rich applications on a daily basis. We found that despite the wide availability of learning resources on the web and decades of research dedicated to workplace knowledge management tools, design professionals still rely heavily on interpersonal help-seeking. Furthermore, while companies have devised a variety of technological channels to answer employees’ help requests, such intermediate tools were often abandoned, and help-seeking conversations shifted to face-to-face learning episodes. Our findings point to design opportunities and shortcomings in the design of communication and collaboration tools that address the needs of design professionals when using feature-rich applications.