As far as I can tell, most people around these parts consider the principle of charity and its super saiyan form, steelmanning, to be Very Good Rationalist Virtues. I basically agree and I in fact operate under these principles more or less automatically now. HOWEVER, no matter how good the rule is, there are always exceptions, which I have found myself increasingly concerned about.
This blog post that I found in the responses to Yvain's anti-reactionary FAQ argues that even though the ancient Romans had welfare, this policy was motivated not for concern for the poor or for a desire for equality like our modern welfare policies, but instead "the Roman dole was wrapped up in discourses about a) the might and wealth of Rome and b) goddess worship... The dole was there because it made the emperor more popular and demonstrated the wealth of Rome to the people. What’s more, the dole was personified as Annona, a goddess to be worshiped and thanked."
So let's assume this guy is right, and imagine that an ancient Roman travels through time to the present day. He reads an article by some progressive arguing (using the rationale one would typically use) that Obama should increase unemployment benefits. "This makes no sense," the Roman thinks to himself. "Why would you give money to someone who doesn't work for it? Why would you reward lack of virtue? Also, what's this about equality? Isn't it right that an upper class exists to rule over a lower class?" Etc.
But fortunately, between when he hopped out of the time machine and when he found this article, a rationalist found him and explained to him steelmanning and the principle of charity. "Ah, yes," he thinks. "Now I remember what the rationalist said. I was not being so charitable. I now realize that this position kind of makes sense, if you read between the lines. Giving more unemployment benefits would, now that I think about it, demonstrate the power of America to the people, and certainly Annona would approve. I don't know why whoever wrote this article didn't just come out and say that, though. Maybe they were confused".
Hopefully you can see what I'm getting at. When you regularly use the principle of charity and steelmanning, you run the risk of:
1. Sticking rigidly to a certain worldview/paradigm/established belief set, even as you find yourself willing to consider more and more concrete propositions. The Roman would have done better to really read what the modern progressive's logic was, think about it, and try to see where he was coming from than to automatically filter it through his own worldview. If he consistently does this he will never find himself considering alternative ways of seeing the world that might be better.
2. Falsely developing the sense that your worldview/paradigm/established belief set is more popular than it is. Pretty much no one today holds the same values that an ancient Roman does, but if the Roman goes around being charitable all the time then he will probably see his own beliefs reflected back at him a fair amount.
3. Taking arguments more seriously than you possibly should. I feel like I see all the time on rationalist communities people say stuff like "this argument by A sort of makes sense, you just need to frame it in objective, consequentialist terms like blah blah blah blah blah" and then follow with what looks to me like a completely original thought that I've never seen before. But why didn't A just frame her argument in objective, consequentialist terms? Do we assume that what she wrote was sort of a telephone-game approximation of what was originally a highly logical consequentialist argument? If so where can I find that argument? And if not, why are we assuming that A is a crypto-consequentialist when she probably isn't? And if we're sure that objective, consequentialist logic is The Way To Go, then shouldn't we be very skeptical of arguments that seem like their basis is in some other reasoning system entirely?
4. Just having a poor model of people's beliefs in general, which could lead to problems.
Hopefully this made sense, and I'm sorry if this is something that's been pointed out before.
To me, charitable reading and steelmanning are rather different, though related.
To read charitably is to skip over, rather than use for your own rhetorical advantage, things in your interlocutor's words like ambiguity, awkwardness, slips of tongue, inessential mistakes. On the freeway of discussion, charitable reading is the great smoother-over of cracks and bumps of "I didn't mean it like that" and "that's not what it says". It is always a way towards a meeting of the minds, towards understanding better What That Person Really Wanted To Say - but nothing beyond that. If you're not sure whether something is a charitable reading, ask yourself if the interlocutor would agree - or would have agreed when you're arguing with a text whose author is absent or dead - that this is what they really meant to say.
I prefer "charitable reading" and not "the principle of charity" because the latter might be applied very broadly. We might assume all kinds of things about the interlocutor's words acting out of what we perceive as charity. For example, "let's pretend you never said that" in response to a really stupid or vile statement might strike many people as an application of the principle of charity, but it is clearly not a charitable reading. And that's good - it's really a different sort of thing, whether desirable or not.
Steelmanning, on the other hand, is all about changing the argument against your position to a stronger one against your position. The "against your position" part is left out of some good explanations in other comments here, but I think it's crucial. Steelmanning is not a courtesy or a service to my interlocutor. It is a service to me. It is my attempt to build the strongest case I can against my position, so I can shatter it or see it survive the challenge. The interlocutor might not agree, if I were to ask them, that my steelmanned argument is really stronger than theirs; that's no matter. I'm not doing it for them, I'm doing it for myself.
When you look at it like this, there should be no danger of confusing the steelmanned argument with the interlocutor's original one. The steelmanned argument is properly yours, it is based on the original argument but should not be attributed to the interlocutor even rhetorically. There's no benefit to the conversation from doing that. You're not doing anyone a favor by pretending they said something they didn't.
In a conversation, live or close to live, charitable reading is always the appropriate and virtuous thing to do, but steelmanning your interlocutor's argument might not be. It often is appropriate, but that isn't a given. Remember, the steelmanned argument is your creation and is meant for you, you owe it to yourself to test your beliefs with it, but not necessarily in the context of this conversation. Not because concealing it is an easier way to victory, but rather because what's steelmanned for you might not be steelmanned or even interesting to your interlocutor. Their argument said A, and you may have found a way to strengthen it further to say B, but they might not want to claim B, to defend B, to agree that B is stronger than A. That said, if you do think the steelmanned argument would be useful to them, by all means introduce it, but explicitly as your own. Some phrases that are commonly said in such cases would be: "I see your point here, and I would even add ... but still, I would disagree...", or "You could also say that...", or you can propose a back-and-forth: "I think this is wrong because of... You might want to reply that... But to that, I would say..." In all these cases, the interlocutor is free to agree or disagree with your explicitly introduced steelman.
Now, going to the example in the post, where the ancient Roman chooses to interpret a progressive argument for increasing welfare as "really" carrying between lines the ancient Roman rationale. He is not doing a charitable reading of his interlocutor's words - they would definitely not agree that this is what they meant to say. And he is not steelmanning anything either, because he hasn't strengthened an argument against his own position; rather, he fortified his existing beliefs by manufacturing another fake confirmation. If he were to modify the progressive's argument in some way that would make it harder for him to interpret it in the ancient-Roman sense, that would be steelmanning.
To sum up:
Sometimes, our native curiosity is a poor guide to the questions we should really be asking.
The Roman will have to see the lack of temples to Annona, read the histories of ancient Rome, experience a whole lot of people making fun of his toga and the police doing nothing to stop it, and marvel at the magic that the common citizens of this new land carry in their pocket.
But even that might not work if the cherished belief is infectious enough. People will lead miserable lives, commit unspeakable acts, deny their own senses, and go to an early grave in order ... (read more)