It's a good thing to keep in mind: if you really want someone who you're pretty sure already disagrees with you to at least entertain an alternative viewpoint,

It's a good thing to keep in mind: if you really want someone who you're pretty sure already disagrees with you to at least entertain an alternative viewpoint, being clever isn't the way. Simple, straightforward and polite is the best point of entry. If they're willing to pay attention, then you can try introducing some complexity in a more intelligent manner. Note the word 'clever' has a lot of negative connotations - highly manipulative people are generally described as 'clever'. Consider also the phrase 'too clever by half' - it's a way of stating that someone isn't trustworthy.