I agree that steelmanning is bad and don’t know what to think of the “charity” cluster of principles (I at least think you should strive to understand what people said and respond as exactly as possible to what they said, not to what seems to you to be the strongest and most rational interpretation; that should only be a consideration for interpreting correctly what they said, if an interpretation being stronger makes it more likely that it was their interpretation; doing otherwise would just not be worth it even if only because it caused misunderstandings, but you’re also liable to be wrong about what interpretation is strongest and understanding people right is hard enough already that you should just not give yourself that kind of additional work because additional effort is better invested in understanding better), but I also generally don’t like the framing of argumentative virtues or the concern for diplomacy, when those work against common discourse patterns. If some discourse patterns are very common in debates, instead of working hopelessly against them, you can find ways to make use of them for your benefit. For example, you can apply specialization and trade to arguments. Two big bottlenecks on figuring out the truth through rational argument are manpower and biases and that helps with both (and especially with manpower, which I think is probably the most important bottleneck anyway).
The situation where this can benefit you is when argument spaces are large, for example when there are a lot of arguments and counterarguments on many sides of a complex issue, including often many incompatible lines of arguments for the same conclusions, and you can’t explore the full space of arguments on even a single side yourself, unless perhaps you spend weeks doing so as your main activity. So there is no way you can explore the arguments on all sides.
Instead, you can adopt the view that seems the most likely to be true to you (you can revise that as you get more information) and try to find arguments supporting that view and not try very hard to find arguments opposing it. This is the opposite of the advice usually given (the usual advice is bad in this situation). And you should argue with people who have other views. These people are more likely to focus on the weakest points in your arguments than you are to do so yourself and on the weakest assumptions you’ve made that you haven’t justified or thought that you needed to justify (I know this is not always true but only claim it’s more likely) and they’re probably going to do a better job of finding the best arguments against your position than you would yourself (also not always true; I just think these two points are more true than not when averaging over all cases). But these two points aren’t that important. The cases where they don’t apply are cases where you might be doing something wrong: if you are aware of better arguments against your position than similarly smart and rational people who disagree with your position, you’ve probably spent more time and effort than you needed to exploring arguments against your position, which you could have spent exploring arguments for your position or arguments about other things or just doing other things than exploring arguments about stuff.
The most important point is that a greater part of the space of arguments can be explored if each person only explores the arguments that support their position, and then they exchange by arguing. A deeper search can be done if each person specializes rather than both exploring the arguments on all sides. And doing a deeper search overall means getting closer to the truth in expectation. Arguing with other people allows exchanging only the best arguments so it should take less time than exploring yourself.
In this situation, you don’t need to be too worried with looking for arguments against your position since you can just leave that to the people who disagree with you. It’s sensible to worry about being biased, but the primary motivation you should get from that worry is a motivation not to make excuses for not spending time arguing with people who disagree with you, rather than a motivation to spend time looking for arguments against your position yourself.
And you should privilege debating with people who disagree with you (so it’s people who have explored different spaces of arguments than you; but arguing with people who share your conclusions for different reasons and disagree with your reasons is very good and I count them as “people who disagree with you”: the disagreements don’t have to be about the final conclusions), who are smart and rational and have thought much about the topic (so they’ll have done a deeper and better search), who have positions that are uncommon and unpopular and that aren’t those of people you’ve already debated before (there will often be not only two positions that are mutually exclusive and there will be many incompatible lines of arguments leading to these positions; you benefit more in expectation from debating with people who have explored things you haven’t already heard about, so things that are uncommon and unpopular or that you haven’t debated people about before).
Some other things that can improve the quality of the search is debates being in written form and asynchronous so people have time to think and can look up the best information and arguments on the Web and check things on Wikipedia. And you should redebate the same things again with the same people sometimes, because l’esprit de l’escalier is a very important thing and you should take care to make it possible for other people to use it to your benefit (including without having to admit that they’re doing so and that they didn’t think of the best response the first time around, because its being known that they didn’t think of the best response the first time around could be embarrassing to them and you don’t want them to double down on a worse line of argument because of that).
I agree that steelmanning is bad and don’t know what to think of the “charity” cluster of principles (I at least think you should strive to understand what people said and respond as exactly as possible to what they said, not to what seems to you to be the strongest and most rational interpretation; that should only be a consideration for interpreting correctly what they said, if an interpretation being stronger makes it more likely that it was their interpretation; doing otherwise would just not be worth it even if only because it caused misunderstandings, but you’re also liable to be wrong about what interpretation is strongest and understanding people right is hard enough already that you should just not give yourself that kind of additional work because additional effort is better invested in understanding better), but I also generally don’t like the framing of argumentative virtues or the concern for diplomacy, when those work against common discourse patterns. If some discourse patterns are very common in debates, instead of working hopelessly against them, you can find ways to make use of them for your benefit. For example, you can apply specialization and trade to arguments. Two big bottlenecks on figuring out the truth through rational argument are manpower and biases and that helps with both (and especially with manpower, which I think is probably the most important bottleneck anyway).
The situation where this can benefit you is when argument spaces are large, for example when there are a lot of arguments and counterarguments on many sides of a complex issue, including often many incompatible lines of arguments for the same conclusions, and you can’t explore the full space of arguments on even a single side yourself, unless perhaps you spend weeks doing so as your main activity. So there is no way you can explore the arguments on all sides.
Instead, you can adopt the view that seems the most likely to be true to you (you can revise that as you get more information) and try to find arguments supporting that view and not try very hard to find arguments opposing it. This is the opposite of the advice usually given (the usual advice is bad in this situation). And you should argue with people who have other views. These people are more likely to focus on the weakest points in your arguments than you are to do so yourself and on the weakest assumptions you’ve made that you haven’t justified or thought that you needed to justify (I know this is not always true but only claim it’s more likely) and they’re probably going to do a better job of finding the best arguments against your position than you would yourself (also not always true; I just think these two points are more true than not when averaging over all cases). But these two points aren’t that important. The cases where they don’t apply are cases where you might be doing something wrong: if you are aware of better arguments against your position than similarly smart and rational people who disagree with your position, you’ve probably spent more time and effort than you needed to exploring arguments against your position, which you could have spent exploring arguments for your position or arguments about other things or just doing other things than exploring arguments about stuff.
The most important point is that a greater part of the space of arguments can be explored if each person only explores the arguments that support their position, and then they exchange by arguing. A deeper search can be done if each person specializes rather than both exploring the arguments on all sides. And doing a deeper search overall means getting closer to the truth in expectation. Arguing with other people allows exchanging only the best arguments so it should take less time than exploring yourself.
In this situation, you don’t need to be too worried with looking for arguments against your position since you can just leave that to the people who disagree with you. It’s sensible to worry about being biased, but the primary motivation you should get from that worry is a motivation not to make excuses for not spending time arguing with people who disagree with you, rather than a motivation to spend time looking for arguments against your position yourself.
And you should privilege debating with people who disagree with you (so it’s people who have explored different spaces of arguments than you; but arguing with people who share your conclusions for different reasons and disagree with your reasons is very good and I count them as “people who disagree with you”: the disagreements don’t have to be about the final conclusions), who are smart and rational and have thought much about the topic (so they’ll have done a deeper and better search), who have positions that are uncommon and unpopular and that aren’t those of people you’ve already debated before (there will often be not only two positions that are mutually exclusive and there will be many incompatible lines of arguments leading to these positions; you benefit more in expectation from debating with people who have explored things you haven’t already heard about, so things that are uncommon and unpopular or that you haven’t debated people about before).
Some other things that can improve the quality of the search is debates being in written form and asynchronous so people have time to think and can look up the best information and arguments on the Web and check things on Wikipedia. And you should redebate the same things again with the same people sometimes, because l’esprit de l’escalier is a very important thing and you should take care to make it possible for other people to use it to your benefit (including without having to admit that they’re doing so and that they didn’t think of the best response the first time around, because its being known that they didn’t think of the best response the first time around could be embarrassing to them and you don’t want them to double down on a worse line of argument because of that).