Experience underlies all kinds of human knowledge and determines how people interact with products and environments. It also influences designers’ knowledge and their design process. An issue not fully addressed in current literature is about the way in which designers’ individual experience influences design tasks. This paper presents two qualitative design case studies that involve experiments employing collaborative design approaches. Case study one focuses on product usability and case study two, sustainable design. Both studies applied an empirical approach; data collected consisted of sketches and audio- and video-recordings. The studies share a common research approach that opens the discussion about designers’ interactions; the way those interactions reveal knowledge and experience, the influence of these interactions upon the design process and approach to design tasks. This paper will present the correlations and discrepancies between these two case studies and the collaborative design approach used in each study, outlining future research endeavors.