When it doesn't work: four causes

Sometimes you find yourself going in circles. In almost all cases, it's one of these four causes, and each has its fix.

1. The prompt contains two contradictory goals

"Keep it short and detailed", "professional but casual". It arbitrates on its own, and usually badly. Fix: make the call yourself, or split it into two prompts.

2. The conversation is polluted

After fifteen exchanges including three changes of mind, it drags everything along behind it. Old instructions contradict recent ones. Fix: open a new conversation and rephrase cleanly. That's faster than correcting.

3. The topic is outside what it knows

Too recent, too local, too specialised. It won't say "I don't know": it will produce something plausible. Fix: give it the material. Paste in the document, the article, the figures. It is far better at working from a provided text than at retrieving it from memory.

4. You're asking for a judgement it can't make

"Is my idea good?" has no answer: it knows neither your market, nor your resources, nor what you're willing to risk. Fix: ask it for objections rather than a verdict. "What are the three arguments against this idea?" gives you something usable.

The general reflex

When it resists, don't repeat the same prompt hoping for better. Change your angle: provide material, drop a constraint, or start from scratch.