Skill: Maintaining "contextual pointers" with your knowledge, both for the sake of evidential sourcing and contextual usage.
The idea here is twofold.
First, many intellectual conversations between people who lack this skill are are random walks through topic space. Each tangential leap is potentially useful for mining relevant evidence from each person's mind... but in conversations exploring an important central thesis it is good to treat the tangents as objects pushed onto a stack in the course of linear conversation. When you go to far afield with a tangent you need the presence of mind to notice that D was inspired by C which was inspired by B, which was profoundly relevant to the pragmatically important question of A. Stepping back to C or B or even A is frequently called for in important conversations but requires contextual mindfulness.
The second use of context is evidential. Being mindful of where evidence comes from (if it can be managed) helps keep track of the value and meaning of evidence. Confabulation induced or permitted by source amnesia, isn't necessarily a bad thing in terms of "usage optimized concepts" but in terms of epistemic hygiene its a killer. It is especially pernicious in modern media environments full of advertising, fiction, and bullshit.
I bring these two sorts of context up because they both involve "context pointers" and together the two kinds of context pointers enable clear "tree formatted thinking" where reasons radiate from a root node, and leaf nodes carry citations to allow validation.
Exercise: verbalise linking concepts with emphasis/stress on key words.
This verbalisation can be either psychic (that is, using the internal dialogue) or vocal if involved in a discussion with a group. When moving from one concept to the next we find a way to express this as a sentence, and by emphasising key words in this sentence we highlight the concepts linked to by the sentence.
I use this sometimes when I want to remember a particular thought and I use the emphasised words as 'semantic tags' in my memory.
Recent brainstorming sessions at SIAI (with participants including Anna, Carl, Jasen, Divia, Will, Amy Willey, and Andrew Critch) have started to produce lists of rationality skills that we could potentially try to teach (at Rationality Boot Camp, at Less Wrong meetups, or similar venues). We've also been trying to break those skills down to the 5-second level (step 2) and come up with ideas for exercises that might teach them (step 3) although we haven't actually composed those exercises yet (step 4, where the actual work takes place).
The bulk of this post will mainly go into the comments, which I'll try to keep to the following format: A top-level comment is a major or minor skill to teach; upvote this comment if you think this skill should get priority in teaching. Sub-level comments describe 5-second subskills that go into this skill, and then third-level comments are ideas for exercises which could potentially train that 5-second skill. If anyone actually went to the work of composing a specific exercise people could run through, that would go to the fourth-level of commenting, I guess. For some major practicable arts with a known standard learning format like "Improv" or "Acting", I'll put the exercise at the top and guesses at which skills it might teach below. (And any plain old replies can go at any level.)
I probably won't be able to get to all of what we brainstormed today, so here's a PNG of the Freemind map that I generated during our session.