Finding the weaknesses.
WHY YOU MUST ASK EXPLICITLY
The model will agree with you by default. Asking "what do you think?" produces validation.
PROMPTS THAT PRODUCE CRITICISM
"What are the three strongest objections to this?" "What would make this fail?" "What am I assuming that might not be true?" "Argue against this as forcefully as you can." "What would a sceptical expert say?"
THE MOST USEFUL ONE
"What assumptions does this depend on?"
Surfacing assumptions is where most flawed plans reveal themselves.
PRESENTING IT AS SOMEONE ELSE'S
"A colleague proposed this. What problems do you see?"
Removes the tendency to be encouraging.
WHAT TO DO WITH THE OBJECTIONS
Take them seriously rather than defending. Some will be weak; one may be the thing you missed.
THE LIMITATION
It does not know your market, your customers or your constraints.
Objections will be generic unless you provided context.
WHAT THIS IS GOOD FOR
Structured self-examination before committing.