The Roman-numeral outlines I learned how to do back in grade school were the bane of my existence. I just can't work with information in that way. Same thing with bulleted lists. Mentally, I lock up when confronted with either one. I need something more organic.
I start out with 3x5 cards, and once I have the plot pretty well figured out I sit down and type them all up, expanding on them as I go. As I'm developing the outline, I skip around a lot; if I have an idea for the dialogue in a particular scene, or want to make sure a subplot gets developed adequately all the way through, I'll work on that. I still get a lot of ideas during this stage, and I make a lot of decisions about whose POV will get used, which get woven in as I see fit. I also make notes in brackest at the beginning of each scene with the time/date, POV, and location--[Sunday, 31 July 2001; Will's POV; Kim's house, late afternoon], for example. That way, my chronology doesn't get all screwed up. Sometimes, I'll make a note to myself about the weather or the overall mood I want to convey in that scene. I even include details that I know aren't going to make it into the final draft, but might help me capture the "feel" I originally imagined days or weeks (or even months) later, as I'm writing the first draft.
By the time I'm done, I have a rough version of the story that, like Uncle Jim's, is about 1/2 to 3/4 the length of the finished version. It ain't pretty, but it tells me exactly where I need to go, and will keep me on track until I get there.