This one-day workshop invites designers, researchers and practitioners whose work might involve design, to collectively speculate about designed artefacts and technologies through the creation of drawing conversations: visual dialogues resulting from the merging of drawings created by different people. The workshop aims to use drawing as an activity for collaborative engagement with ambiguity, interpretation and mutual learning. Through drawing activities, we aim to join in Venice's rich creative traditions, and develop speculative visualisations in order to find common grounds between the diverse research interests of our organisers and participants.