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I think this is a really nice idea on paper, but I'm unsure about how it will actually work out. We have a tendency to vilify those who don't share our views and because of this there is a serious chance from this discovery source being impossible to stomach due to massive insults and gross over-assumptions.
A team of journalists, programmers and digital strategists is proposing a tool that would help people discover stories being read by people unlike them.
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I think the point-counterpoint type of debate has worked before, though. A lot would come down to implementation. I rather like how Amazon does the "The most helpful favourable review" vs. "The most helpful critical review" thing.
Think back to the last few political debates you've watch, Canadian or American, and tell me with a straight face that point-counterpoint debate works for political issues. It still gets way too heated and way too personal.
I don't watch televised political debates any more because I've found neither side of the dominant two parties frequently talks about issues I actually care about (usually they go un-debated), and then, typically the one who I think should win rarely does because first past the post is a horribly broken system in races where there's > 2 candidates.

That being said, I've found it does work well for financial issues/advice. I do also think there's a lot of value to be had in getting differing perspectives, and some books that do it well are, for example: The Unlikely Disciple: A Sinner's Semester at America's Holiest University, and chapters of AJ Jacobs' The Year of Living Biblically: One Man's Humble Quest to Follow the Bible as Literally as Possible (where he talks to people with far more literal interpretations than his own).
I agree with all your examples. I think the project they are describing would be a lot more successful if they started there and worked up towards political topics. But they said they are starting with politics which is is akin to starting a toddler off crawling by setting them down on their feet and watching what happens.
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