This document outlines an agenda for a dialogue on designing with dialogue at the Strategic Innovation Lab on September 15, 2008. The agenda includes sections for participants to introduce themselves, share a recent work challenge involving communication, and discuss why designing with dialogue is important. It notes that complex problems are larger than any individual, collective wisdom is needed for design, organizations themselves are complex problems, isolated solutions are insufficient, stakeholders must own transformation initiatives, and diverse viewpoints and needs must be considered in design.