Projects focusing on preserving cultural heritage are most usually instigated by a researcher. Yet, the question arises ‘whether such projects are beneficial for the studied communities?’ This paper describes the first part of a co-reflective, design research case study exploring through design the dynamics of the disappearance of culture heritage. By guidelines for respectful design (synthesized from literature) we sought to find an indigenous community to work with and a design direction beneficial for them. Our initial visits to three indigenous communities in Malaysia, where we developed and introduced empathic design probes, led to the Penan community becoming particularly interested in the project. A design direction arose, which aimed to explore technological design as a means to spark intergenerational conversations on being a Penan.