[stanleydrew]

This can be dangerous as well though. Most people aren't naturally adversarial and get uncomfortable pushing down paths where you don't know the answer or seem unprepared.

You often won't get someone to really challenge your assumptions unless they have some meaningful motivation. So you may have to listen in a different way than you're used to, or push people a bit to get them really comfortable with telling you things they might think you don't want to hear.