An AI assistant like IBM's Debater can help challenge project decisions from multiple perspectives, enriching the human decision process. The author advocates adopting different lenses like ESPRIT (economic, social, political, religious, intellectual, technological) to examine a project's foundations. An AI assistant debating from varied viewpoints could provide broader knowledge than humans alone while still allowing humans to make the final call. Such debates improve critical thinking, alignment around key drivers, and the quality and rationale of decisions through a collaborative learning process.