# optioning: another way to have interesting conversations.

i'm really bad in conversations. in real life i tend to be too silent and superficial. in emails i tend to write too much, sometimes being too insensitive. i'm pretty sure i often overwhelm the recipient with the quantity because i often don't get any replies. and my writing style is not very coherent, i just keep rambling about random stuff. reading my writing is probably quite hard. and often people don't even like to write, so then i'm having hard time to communicate with such people.

i think there are two big problems with my art of communication. the quantity problem: i'm tempted to ask too many questions. it's pretty much infeasible to answer them all in one message. and even if you were able to do, you have to go question by question which makes the email to have a very unnatural format.

then there's the quality problem: some of the questions are very hard, that nobody knows the answers to. the recipient has no idea how to respond to such a question, and as such is very discouraged from responding at all.

i think i found a way to address both issues. rather than asking all the questions in one letter, i focus on asking a single question. if i have more, then i might start tracking the list of questions or topics that needs further discourse, and simply ask them at a later point. furthermore i also provide 2-4 answer options and the recipient simply must choose the least wrong answer with an optional comment.

i don't think one needs to obsess about the answer quality since the expectation is to choose the least wrong. i'd expect people would mention a better answer if they have in the comment. the point is to force people to make a decision. in case of indecisive people you can pretty much bypass the indecisive consciousness and get an answer right from the subconsciousness. for your email partner the whole thing is like one of those conversational adventure games (e.g. telltale's walking dead or life is strange).

however the downside is that this is much harder on the questioner. they really need to think a lot what single question would be the one that uncovers the most information for them about the other person. it's an intriguing puzzle game. it's somewhat similar to debugging computer programs. but here you are debugging humans. you create several hypotheses and the other person tells you which one is the closest. or it's like that "hot and cold" kid game where you hide something and the kid has to find it with you converting their distance from it into temperatures.

(edit: to generate good answers, the questioner needs to put themselves in to the answerer's shoes. they questioner must see the question from the answerer's perspective. i think this can bring a lot of clarity to the questioner, and thus gives a big boost to feeling empathetic to the other person.)

it's a very slow process but if one has patience and the other person is willing to play this honestly, i think one can learn quite a lot of deep things about the other person. and it's very easy to start. you start with something like "how are you these days? good/bad" and then the rest of the questions sort of give themselves. e.g. "what makes you happy/sad these days?" for the above one. if unsure, you can always ask "why?" for the previous answer and try to come up with some realistic answers to it.

i think it's important to play this over email rather than instant messaging. sometimes it might take several days to come up with the next question or even with the answer. email supports labeling and threading by default so it's the best medium for slow communication.

such a discussion could be almost neverending. however given the fact that one could go at it very slowly, that shouldn't be too much of a problem. one could easily talk like that with multiple people if they are not bothered by the fact that the delays between the individual messages with a given person will keep growing. also, if you have lots of questions that you want to ask a single person, you could have multiple parallel threads with them. though i'd expect that could be quite strenuous to maintain.

to give a small taste how this could look like, i've created a demo about this at @/dialog. it's just a dumb dialog tree. it obviously cannot have as much nuance as a realtime conversation could have. but it was quite fun to write it. it was quite tiring to write it though so therefore it's very short.

btw, this idea could take many other forms. for instance that dialog tree from above could be a collaboratively edited one, implemented similarly like a wiki. that way it could grow quite big. with some sort of trusted peer review it could stay quite sensible. or one could make an app for it, that keeps asking you questions very slowly. and then its developer just keep adding new nodes based on the stats where the most people are stuck currently. the developer's goal would be to split people along the nodes as much as possible. or maybe one could make a live tv interview show where the host comes up with good questions that both the viewers and the interviewee tries to answer. first the interviewee tries to guess the viewers response, and then analyze those results. i think this could give a good insight how someone thinks since they have to put themselves into other people's shoes. the socractic method has similarities to this method too.

i'm not sure what the name of this technique would be. i went with "optioning" since the primary task is to give options to the other person.

anyways, at least i now have a new technique in my toolset, maybe i'll use it one day too.

published on 2020-12-30, last modified on 2021-02-08

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