I'm not a natural outliner. In truth, I'm actually entirely the opposite. *twitches a little at all the -ly's* So how does someone like me, who doesn't usually outline *and also hates it like I hate broccoli*, start an outline in the first place?
There's no concrete guideline, though some writing self help books would tell you otherwise, because all writers are different and they ultimately have to find what works best for them.
I usually start with breaking out a subheading for each chapter. After deciding how many chapters I have (generally twenty to start because it's a nice do-able, even number), I break out the documents into acts and determine how many chapters would need to go into those acts to fulfill the information needed to get through to the audience. If you really want to go basic, a three-act breakout would suffice (introduction, climax, resolution). I like to put in four acts just because the pacing changes slightly in each act (or at least that's the initial plan *laughs*). So...
Act One - Introduces the characters, the world (if world building is a high point), and the central conflict.
Act Two - This would be what I like to call the buildup. This is where the main events happen that would eventually lead to Act Three, the climax. A good chunk of my chapters will be lumped into Act Two because they are the events that propel the story forward to its pinnacle point.
Act Three - This is where the events from Act Two will hit their breaking point. The characters need to make a decision regarding the central conflict. The make or break moment, if you will.
Act Four - Now, if Acts One-Three were the appetizer, soup/salad, and main courses, this would be the dessert. The resolution. This is where all of the questions should be answered (unless it's a series) and where everything should tie out. The result should be satisfying and adds that little something that puts the reader at ease.
This post not only serves as a writers' tip thing of sorts, but also to help me get the writer gears in motion. Mid-post, my new characters had invaded my head space and started conversations of their own. *laughs*
If you think my methods are still a little too jumbled and full of malarky, you can check out these other links for great outlining tips:
Chris' blog here and here
Advanced Fiction Writing
**image from darkgreencabochon