When you work with AI long enough, you start to notice it makes the same kind of mistake over and over.

"You're coming on too strong, dial it back." It shrinks and goes meek. "Stop being meek." It comes on strong again. Each time you point something out, it apologizes sincerely. The next round, the same type of problem comes back from a different angle. After a while you realize you're babysitting the AI instead of working with it.

This isn't because the AI is bad. It's a design quirk: today's AI is tuned to satisfy the user. The quirk won't go away. But if you change how you work with it, you can still get work done together.

This piece is about that — five patterns of the quirk, and an operating mode that gets ahead of them instead of correcting them in flight.

Five quirks in a single evening