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CCC comments on Rationality Quotes September 2014 - Less Wrong
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I don't see what to do about gaps in arguments. Gaps aren't random. There are little gaps where the original authors have chosen to use their limited word count on other, more delicate, parts of their argument, confident that charitable readers will be happy to fill the small gaps themselves in the obvious ways. There are big gaps where the authors have gone the other way, tip toeing around the weakest points in their argument. Perhaps they hope no-one else will notice. Perhaps they are in denial. Perhaps there are issues with the clarity of the logical structure that make it easy to whiz by the gap without noticing it.
The third perhaps is especially tricky. If you "re-express your target’s position ... clearly" you remove the obfuscation that concealed the gap. Now what? Leaving the gap in clear view creates a strawman. Attempting to fill it draws a certain amount of attention to it; you certainly fail the ideological Turing test because you are making arguments that you opponents don't make. Worse, big gaps are seldom accidental. They are there because they are hard to fill. Indeed it might be the difficulty of filling the gap that made you join the other side of the debate in the first place. What if your best effort to fill the gap is thin and unconvincing?
Example: Some people oppose the repeal of the prohibition of cannabis because "consumption will increase". When you try to make this argument clear you end up distinguishing between good-use and bad-use. There is the relax-on-a-Friday-night-after-work kind of use which is widely accepted in the case of alcohol and can be termed good-use. There is the behaviour that gets called "pissing your talent away" when it beer-based. That is bad-use.
When you try to bring clarity to the argument you have to replace "consumption will increase" by "bad-use will increase a lot and good-use will increase a little, leading to a net reduction in aggregate welfare." But the original "consumption will increase" was obviously true, while the clearer "bad+++, good+, net--" is less compelling.
The original argument had a gap (just why is an increase in consumption bad?). Writing more clearly exposes the gap. Your target will not say "Thanks for exposing the gap, I wish I'd put it that way.". But it is not an easy gap to fill convincingly. Your target is unlikely to appreciate your efforts on behalf of his case.
With regards to your example, you try to fix the gap between "consumption will increase" and "that will be a bad thing as a whole" by claiming little good use and much bad use. But I don't think that's the strongest way to bridge that gap.
Rather, I'd suggest that the good use has negligible positive utility - just another way to relax on a Friday night, when there are already plenty of ways to relax on a Friday night, so how much utility does adding another one really give you? - while bad use has significant negative utility (here I may take the chance to sketch the verbal image of a bright young doctor dropping out of university due to bad use). Then I can claim that even if good-use increases by a few orders of magnitude more than bad-use, the net result is nonetheless negative, because bad use is just that terrible; that the negative effects of a single bad-user outweigh the positive effects of a thousand good-users.
As to your main point - what to do when your best effort to fill the gap is thin and unconvincing - the simplest solution would appear to be to go back to the person proposing the position that you are critically commenting about (or someone else who shares his views on the subject), and simply asking. Or to go and look through his writings, and see whether or not he addresses precisely that point. Or to go to a friend (preferably also an intelligent debator) and asking for his best effort to fill the gap, in the hope that it will be a better effort.
So, you go back to the person you're going to argue against, before you start the argument, and ask them about the big gap in their original position? That seems like it could carry the risk of kicking off the argument a little early.
"Pardon me, sir, but I don't quite understand how you went from Step A to Step C. Do you think you could possibly explain it in a little more detail?"
Accompanied, of course, by a very polite "Thank you" if they make the attempt to do so. Unless someone is going to vehemently lash out at any attempt to politely discuss his position, he's likely to either at least make an attempt (whether by providing a new explanation or directing you to the location of a pre-written one), or to plead lack of time (in which case you're no worse off than before).
Most of the time, he'll have some sort of explanation, that he considered inappropriate to include in the original statement (either because it is "obvious", or because the explanation is rather long and distracting and is beyond the scope of the original essay). Mind you, his explanation might be even more thin and unconvincing than the best you could come up with...
I think the idea was, 'when you've gotten to this point, that's when your pre-discussion period is over, and it is time to begin asking questions'.
And yes, it is often a good idea to ask questions before taking a position!
Entirely within the example, not pertaining to rationality per se, and I'm not sure you even hold the position you were arguing about:
1) good use is not restricted to relaxing on a Friday. It also includes effective pain relief with minimal and sometimes helpful side-effects. Medical marijuana use may be used as a cover for recreational use but it is also very real in itself.
2) a young doctor dropping out of university is comparable and perhaps lesser disutility to getting sent to prison. You'd have to get a lot of doctors dropping out to make legalization worse than the way things stand now.
My actual position on the medical marijuana issue is best summarised as "I don't know enough to have developed a firm opinion either way". This also means that I don't really know enough to properly debate on the issue, unfortunately.
Though, looking it up, I see there's a bill currently going through parliament in my part of the world that - if it passes - would legalise it for medicinal use.
Have you read “Marijuana: Much More Than You Wanted To Know” on Slate Star Codex?
No, I have not.