David Dean – AI, Judgment, and the Work We Don’t Document

Join David Dean, author of An Inbox Between Us, as he sits down with Allison Herbert, our very own Product Coffee Librarian, to talk about what happens when AI enters the space between the organization we document and the organization we actually live in every day.

Most organizations have process maps, org charts, goals, and operating models. They also have the reality of how work gets done: spreadsheets, workarounds, judgment calls, undocumented expertise, Slack threads, hallway conversations, and the people quietly carrying the context that keeps everything moving.

AI works with the information it’s given. That means it can help surface patterns that were previously hidden, scattered, or simply accepted as part of the job. It can also expose broken processes, unclear accountability, invisible work, and places where automation may amplify problems rather than solve them.

David and Allison will explore what AI reveals about how organizations actually function, where judgment and accountability still matter, and the role invisible work plays in keeping things moving.

We’re also excited to make this our kickoff discussion for the next Product Coffee Book Club selection, giving members a chance to meet David, hear the story behind the book, and begin exploring its ideas before we dive deeper together.

If you’re a product manager, product leader, or anyone working through the realities of AI adoption inside a complex organization, I think you’ll find this discussion both practical and thought-provoking.