Whenever I used a word like adumbrate, my Grandmother would say, “Your high ejaculations are too copious for the low dominion of my comprehension.” Gran always had a wicked sense of humor. She ran a beauty salon for decades. One day, a customer, who apparently hadn’t had a very good day, plopped down in Gran’s chair and said, “I’ve had such a bad day, I don’t know which end is up.” To which Gran replied, “Well, you’d better figure it out soon, because I have to shampoo one of them.”

I’ve had some recent requests and discussions about outlining in Word, and quite a few people have said that they find Word’s outlining feature to be more than a tad bit inscrutable. That’s a shame, because, as a tool, Word’s outlining feature is really quite powerful. So much so, that I find I use it on a regular basis.

Before I discuss outlining, though, I’m going to digress a bit to talk about Word’s fundamental purpose, which is to be a writing tool. Nearly everything we’ve done with Word, and nearly everything we continue to do with Word, is designed to relieve the user of having to think about the mechanics of writing, thereby allowing her to focus on the content. Don’t want to worry about common spelling errors? Let Word do it. Don’t want to have to type in long paragraphs of boilerplate text? Let Word do it. Don’t want to worry about line breaks and page breaks? Let Word do it. Want to have successive side-by-side paragraphs align at the top with each other yet not have to figure out how much vertical space to add beneath the shorter paragraph? Drop in a table, and let Word do it. Don’t want to bother with counting spaces in order to center a title? Let Word do it.

Now astute denizens of the Web might be quick to point out Adam Engst’s discussion of the hypothetical WriteRight, in which he points out that there is no good word processor for professional writers. And, I should add, Adam is absolutely correct on that score. There is no word processor, including Word, that’s perfectly suitable for professional writers.

So, Rick, if Word’s supposed to be a writing tool, why do professional writers curse it so much? Well, professional writers represent only a small portion of the overall market for word processors. The majority of people who use Word have a primary job function that includes having to do some writing, yet where writing isn’t the core of their work.

The needs of most Word users aren’t the same as the needs of professional writers. A great example of this is the word count feature, over which reviewers like Adam Engst, who happen to be professional writers, have been knocking Word for quite some time. Most Word users don’t really care about word count. For the sake of those users, and not for the sake of getting rave reviews from professional writers, we didn’t spend a great deal of time trying to make word count faster. We spent time working on improvements that would be more relevant to our more common users. It���s a shame that Adam doesn’t understand this; hence his reaction to the snickers he heard when we mentioned that we’d sped up word count.

But, I’ve digressed enough to make the point: Word’s purpose is to be a writing tool. If we want to really understand Word’s outlining feature, we have to look at it from this point of view. In particular, we have to look at it terms of the workflow of someone who’s writing certain kinds of documents for which outlining is a useful step in the process.

This, I think, is one of the reasons people find Word’s outlining feature to be inscrutable. We didn’t implement it as a tool for creating outlines—i.e. a document that looks like an outline when you switch from outline view to page layout view. Rather, we implemented it as a way to organize your thoughts as you work on a document like a report or a lengthy essay.

Word’s outline view offers a number of tools for direct manipulation of entire sections of a document. For example, if you click on a heading, the heading and any items that fall under that heading are selected as well. So, if you drag that heading to another location in the document, everything up to, but not including, the next heading of the same level gets dragged along with the heading you drag. You can expand or collapse headings by double-clicking on the hollow “plus” sign in the margin to the left of the heading.

Because Word’s outlining feature is geared toward creating documents that are not, in and of themselves, outlines, the feature is tightly coupled with Word’s styles. Each of the pre-defined heading styles has an associated outline level. Indeed, I find it helps to think of Word’s outlining feature as really nothing more than a more direct way to apply heading styles to specific paragraphs within my document. Demoting a paragraph applies the heading style associated with the next lower outline level. Promoting a paragraph applies the heading style associated with the next higher outline level.

The nice part about this coupling between styles and outline levels is that it makes creating a table of contents almost trivial. Once you’ve finished your document, you simply place the insertion point where you want the table of contents to appear, and select “Index and Tables…” from the Insert menu, click on the “Table of Contents” tab, select the format you want, and click .

The down side is that adding numbering isn’t all that straightforward. The best way is to modify the heading styles, but there is no way to apply outline numbering to all the heading styles at once—at least no way out of the box. You could add outline numbering to the “Normal” style, but you probably don’t want that. One work-around would be to use “Body Text” for “Normal” paragraphs, but that doesn’t work within Word’s outline view all that well.

Another way to add numbering is to change the based-on chain for heading styles. A very good tutorial on how to do this can be found here. If you find that you create numbered outlines often, then I highly endorse this tutorial’s suggestion to save these changes in a template.

A general tutorial on outline view, written by Word MVP Dave Rado, can be found on the MVP’s web site here (if you’re using Safari, you’ll need to reload the page after you’ve clicked on the link). The pictures show Win Word’s UI, but the functionality and keyboard shortcuts are the same for Mac Word.

I’d also recommend spending some time just playing around with Word’s outline view to see how it behaves. Once you’ve become comfortable with outline view, you might find yourself using it in creative ways. In fact, one of the ways I use it most often is when I’m taking minutes during a meeting. I’ll type in the agenda items at heading level 1, and add any decisions under those agenda items at body text level. When we’ve finished with an item, I collapse the item’s heading in outline view. If we suspend the discussion on an item until later in the meeting, then I leave the item open with a blank line of body text beneath it. That way, I can easily keep track of which items are open, the items for which we’ve made decisions, and those items we’ve yet to discuss.

So, paradoxically, Word’s outline view is primarily designed to facilitate writing documents other than outlines and not to be an outliner like, say, OmniOutline. Having said that, I should point out that it’s still possible to create an outline that looks like an outline when you print it out. In fact, it’s really rather easy. Just print your document from within outline view.