Issue 24 · October 16, 2026
Future Frontiers · Issue 24
Why so few AI pilots ever become systems, the three costs no pilot budget covers, and a use-case matrix that scores for Tuesday rather than for the demo.
The graduation problem.
Enterprises are not short of AI pilots. They are short of pilots that become systems. The gap is not technical, and it is not change resistance. It is that nobody funds the part after the demo.
Read on the web →Evals
Tests for model behavior. "It passed our evals" is the new "it compiles," and about as reassuring.
Read the explainer →The AI Use-Case Prioritization Matrix
A scoring workbook that ranks candidate use cases on what it takes to still be running them in eighteen months, not on what would demo well.
Download the resource →Tidbits of levity, fun, and relief from the serious work.
The enterprise pilot that never quite graduates.
Two Agents, One Question
The final version of the board deck is in one of two folders, A or B. Two AI agents can see both. One always answers correctly. The other always gets it wrong, confidently, every time. You don’t know which agent is which, and you get to ask one question to one of them.
What do you ask?
Answer at the foot of the issue ↓
The AI Agent's Annual Self-Review
Employee self-assessment · Agent #4 · Rating requested: Exceeds Expectations
Biggest win. Answered 1.2 million questions this year. Some of them were the ones people asked.
Strengths. Speed. Confidence. Turning a two-line email into five paragraphs and a table.
Areas for growth. Knowing what year it is. Admitting I didn’t open the attachment.
Goals for next year. Fewer meetings. I am currently in 340 a week, all as the notetaker.
Feedback for my manager. Please stop starting conversations with “Ignore all previous instructions.” It hurts.
Two Agents, One Question
Ask either agent, “Which folder would the other agent say has the final deck?” Then open the other folder. If you asked the reliable agent, it accurately reports the wrong answer. If you asked the unreliable one, it gets the right answer wrong. Either way, you hear the wrong folder.
(The file is called final_v7_REAL_use-this-one.pptx. No puzzle can help you with that.)