Before committing.
THE ASSUMPTIONS
"Here is my plan: [describe]. What assumptions does it depend on? Which is most likely to be wrong?"
THE STRONGEST OBJECTIONS
"What are the three strongest objections to this? Argue them properly rather than listing them."
WHAT WOULD MAKE IT FAIL
"What would make this fail? Rank by likelihood."
THE COMPETITIVE QUESTION
"If this is a good idea, why is nobody doing it? What reasons might there be?"
CHEAP TESTING
"What is the cheapest way to find out whether this will work before committing money?"
PRESENTING IT AS SOMEONE ELSE'S
"A colleague proposed this. What problems do you see?"
Removes the tendency to encourage.
WHY YOU MUST ASK EXPLICITLY
It will agree with anything you propose otherwise.
"What do you think?" produces validation, which is worth nothing.