Yesterday I told a terrifying story about someone who used the outline format as a vicious weapon. Even without experiencing that trauma, many of us find outlines intimidating (or, at best, tedious).

When you learn how to use them, though — and if you only outline when you really need to — a good document outline can really improve the quality of your writing and make the whole process faster. How? More of that old magic I’m always talking about. An outline takes the invisible structure in your document and makes it visible.

As I said yesterday, a document outline is a map of the relationships between ideas. That’s incredibly valuable when you’re trying to perfect a document, because it lets you see how each piece of it is connected to the document’s purpose (and by how far removed).

If you’re working with an existing document (say, trying to trim it down), you should be able to plot every single sentence into an outline. It’s either a new idea, or supporting evidence for an idea you’ve already established. A good outline should show you how well the ideas and evidence flow, what’s out of order, and where you’re spending too many words on minor details.

Group Your Ideas

Most of the time, you’ll use an outline more for prewriting than for revision. In that case, your goal should be to build a balanced, effective structure from the ground up.

Start by grouping your ideas. Come up with a handful of categories that can evenly contain everything you need to say. These are going to be the Roman numerals on your outline, the venues in which you’ll discuss your topic. Each of these categories should be directly related to your topic.

If you’re working on a blog post or a business memo, these are your section headings. If it’s a five-paragraph essay, these are paragraphs two through four. If it’s a book…these might be chapters, but they’re more likely to be “volumes.” In a three-act novel, for instance, I’d have Act I, Act II, and Act III as my Roman numerals. In a textbook about writing, I might have Prewriting, Writing, and Rewriting.

Once you’ve figured out your groups, start adding some ideas to them — actual things you want to say. Make sure each fits cleanly in one of your groups. If not, you might need to rethink the categories (or cut out that point).

Organize Your Ideas

Now it’s time to choose an organization method. Look at your ideas, look at the groups they fall into, and then look at your purpose (or topic). What’s the best way to organize these pieces to build the structure you really want?

The answer to that is your outline. Go ahead and start rearranging your groups (and ideas) into a nested format. You don’t have to start labeling the lines yet (your big Bs and little Cs), but start drawing the relationships, like so:

Introduction

My topic

Why it matters

Why you should listen to me

First category

How it’s related to the topic

Why it matters

What you should do about it

If they don’t work — say, for instance, you just can’t make one group fit cleanly anywhere — then that’s a problem you would have encountered in your writing, too. You would have been typing (or scribbling) happily along, expounding to your heart’s content, and then realized the next obvious thing to do would be to write your conclusion, but you’d left out a major part of your argument. And, even worse, you really can’t think of any clean place to cram it in. I know, I’ve been there.

It’s much easier to fix that sort of problem at the planning stage, because otherwise it’s going to involve some extensive rewriting. Maybe you need a new organization of your groups, or maybe you need to cut the awkward group after all. Maybe you need to redistribute your ideas, or go back to square one and make up all new categories. Trust me, even if it comes to that worst case, it’s still a lot less work than writing yourself into a corner before you ever know there’s a problem.

Making it Official — Using the Standard Outline Format

Once you’ve put in that much work, it’s worth going the final step and putting the whole thing into a formal outline. You’ve got your organization settled now, but a formal outline will force you to think through more detailed issues like the balance and depth of your arguments.

That’s often the step that people find most intimidating, but once you’ve got a category list and major ideas, it’s really just a little extra paperwork to finish it off. Come back tomorrow and I’ll review the rules (and benefits) of the standard outline format.