It seems like the annual Less Wrong survey is already doing a good job asking simple, easily classified/quantified questions like "where are you from". So the comparative advantage of these interviews might be asking longform questions like "what's the most valuable thing you found in a meetup", "what's the thing you are most surprised does not appear on Less Wrong", etc.
Other half-baked question ideas:
Do you have a note-taking system? How does it work? What software do you find really useful in general? (Google Chrome extensions, webapps, phone apps, etc.) (If anyone is curious, I described my note-taking system here. It's a nice low-pressure way to keep track of ideas for Less Wrong posts that I will probably get around to writing at some point.)
How has rationality informed the things you do in your career? What rationality lessons have you learned in the course of your career?
What rationality techniques do you find most useful? Have you discovered/learned of any that Less Wrong doesn't discuss?
James Miller comes to mind as a person to request an interview of; he's an tenured economics professor.
Thanks, really good suggestions! I like the idea of asking about technologies. and it would be a worthwhile repository - useful technologies that lesswrongers' have found. (as well as your other ideas) I probably would not have thought of that one, even though I would really benefit from it.
As was commented by Clarity:
(http://lesswrong.com/lw/m9e/a_survey_of_the_top_posters_on_lesswrong/)
(http://lesswrong.com/lw/m9e/a_survey_of_the_top_posters_on_lesswrong/cgyo)
I am more than happy to start a small project in interviewing LW'ers of active participation.
With that in mind:
2a. what would generally be good questions for interviews of lesswrongers?
Disclosure: I am personally concerned with raising the profile, status and existence of in-person meetups, so I would probably include a few questions about:
I am keen to try to set up one interview every week or two. (willing to put in 2 hours of effort each week towards contacting people, planing questions, talking to them, interviewing on record, tidying up the audio, then publishing the interview. Est 15-45min interview)