This book records the very first Working Conference of the newly established IFIP Working Group on Human-Work Interaction Design, which was hosted by the University of Madeira in 2006. The theme of the conference was on synthesizing sketches within different approaches to analysis and design of human-work interaction. Authors were encouraged to submit papers about design sketches- for interfaces, for organizations of work, etc. - that they themselves had worked on. During the conference, they presented the lessons they had learned from the design and evaluation process, citing reasons for why the designs worked or why they did not work. In this way, researchers, designers, and analysts confronted concrete design problems in complex work domains and used this unique opportunity to share their own design problems and solutions.