Never ask a lawyer if it's OK to do something (it's always "no"). Ask them to explain the risks in doing so.

Never ask a programmer if something is possible (it's always "yes"). Ask them to explain what is involved doing something.

Never ask a doctor if something will make you better (it's always "maybe"). Ask them to explain the conditions under which a treatment/procedure will work and what could go wrong.

@davetron5000 Hah, so recognisable! As a programmer, I wholeheartedly concur.

"Possible" and "possible within a week or two" are two very different things, and nerdy me can sometimes have a hard time figuring out which one is being asked.

Same as "easy" vs. "quickly done", I made that mistake too. Yeah, something can be easy but still months of easy work.