Information technology support is hard to find for the early design phases of the architectural design process. Many of the existing issues in such design decision support tools appear to be caused by a mismatch between the ways in which designers think and the ways in which information systems aim to give support. We therefore started an investigation of existing theories of design thinking, compared to the way in which design decision support systems provide information to the designer. We identify two main strategies towards information system support in the early design phase: (1) applications for making design try-outs, and (2) applications as autonomous reasoning agents. We outline preview implementations for both approaches and indicate to what extent these strategies can be used to improve information system support for the architectural designer.