I think that even with sympathy and trying, you are at risk of constructing an argument that has parts that are good-for-you, not good-for-your-audience, simply because your model of them is not perfect and you don’t have practice making arguments from their perspective. (Of course, unless you actually do have practice making such arguments; but I guess most people don’t.)
This is related to a problem with steelmanning—if “steelmanning” means providing the strongest support for your opponent’s perspective, does it mean “strongest” from your perspective, or “strongest” from their perspective? (When a liberal makes a steelman of a conservative policy proposal, should they use the best possible liberal arguments in favor of the policy, or best possible conservative arguments?) In my opinion, it should be strongest from your perspective, because the entire purpose of the exercise is for you to find the value in your opponent’s arguments. But this implies that your opponent will probably not be happy with the steelman of their position, because from their perspective, it defends the right thing for the wrong reason.
I think that even with sympathy and trying, you are at risk of constructing an argument that has parts that are good-for-you, not good-for-your-audience, simply because your model of them is not perfect and you don’t have practice making arguments from their perspective. (Of course, unless you actually do have practice making such arguments; but I guess most people don’t.)
This is related to a problem with steelmanning—if “steelmanning” means providing the strongest support for your opponent’s perspective, does it mean “strongest” from your perspective, or “strongest” from their perspective? (When a liberal makes a steelman of a conservative policy proposal, should they use the best possible liberal arguments in favor of the policy, or best possible conservative arguments?) In my opinion, it should be strongest from your perspective, because the entire purpose of the exercise is for you to find the value in your opponent’s arguments. But this implies that your opponent will probably not be happy with the steelman of their position, because from their perspective, it defends the right thing for the wrong reason.