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.
Exercise A: For some policy that someone is carrying out today, starting as close to the object level as possible (answering an email, making a phone call, buying something at the store), ask about the consequences, and the consequences of the consequences. Identify the consequences that are desirable or that the action is being carried out for-the-sake-of. State the goal in abstract terms. Ask whether achieving the goal has further consequences - even things terminally desirable often have other, instrumentally desirable or undesirable consequences. Trace out the chain of specific events and the abstract instrumental and terminal goals they correspond to.
Exercise B: For each goal node, find some other policy - not necessarily a superior policy, but some other policy - that would be helpful for the same goal, not necessarily in the same way. (The point being to unanchor your concept of that goal from the exact, specific means of achieving it. This also obviously starts on the habit of searching for superior alternatives.)