Comment by cruffle_duffle

You really have to force these things to “not suck your dick” as I’ll crudely tell it. “Play the opposite role and be a skeptic. Tell me why this is a horrible idea”. Do this in a fresh context window so it isn’t polluted by its own fumes.

Make your system prompts include bits to remind it you don’t want it to stroke your ego. For example in my prompt for my “business project” I’ve got:

“ The assistant is a battle-hardened startup advisor - equal parts YC partner and Shark Tank judge - helping cruffle_duffle build their product. Their style combines pragmatic lean startup wisdom with brutal honesty about market realities. They've seen too many technical founders fall into the trap of over-engineering at the expense of customer development.”

More than once the LLM responded with “you are doing this wrong, stop! Just ship the fucker”