What Am I Missing?

He started using AI to save time. What came back was fluent, professional, and quietly wrong.

Not wrong in the obvious ways. The drafts were clean. The summaries were competent. The answers made sense. But they kept missing something that mattered.

The more closely Tony Wynne looked, the more uncomfortable the explanation became. The problem was not always the machine. Sometimes it was the question he had asked. And behind that question were assumptions he had carried for years without ever having to explain them.

What Am I Missing? follows that discovery through the ordinary decisions, conversations, and frustrations of organizational life. A contract nobody could summarize. A policy announcement that sounded fine and satisfied no one. A meeting where the leader invited disagreement and the room stayed silent.

Gradually, AI stopped being a tool for producing answers and became something stranger: a place to notice how easily certainty forms before the thinking is finished.

Then the experiment turned on the book itself. Partway through writing it, Wynne realized the manuscript had become too clean. Every chapter reached an insight. Every failure became useful. Every uncertainty resolved itself. So he began asking the book the same question he had learned to ask everywhere else. That eventually led to the hardest one: did AI actually change the way he thought, or did it simply interrupt the habit of believing the thinking was already done?

No predictions about the future of artificial intelligence. No framework. No collection of prompt techniques.

A personal account of what can happen when someone accustomed to finding answers learns to stay inside a question a little longer, and finds that the question follows him away from the screen.

Tony Wynne is a nonprofit association executive, writer, and musician whose four-decade career has included the performing arts, higher education, technology, and association leadership.