Mastering Word 2007 .. 2013 Outline Structure and Headings

Since 2007, Word is killing me on a regular basis when it comes to chapter numbering. Many forum threads prove I'm not alone. It seemed to be pretty easy and intuitive in Word 2003 and appeared to be totally out of control since Word 2007.
I have finally figured out how it can be done right and want to let you all know (plus keep this for personal reference).

My goal is to create a document where chapters are outlined and numbered, and deeper chapters contain the numbers of their parent chapters, just like this:

1. Level 1 Chapter
blabla

1.1 Level 2 Chapter
blablabla

1.1.1 Level 3 Chapter
etc

1.2 Level 2 Chapter
etcetc

1.2.1 Level 3 Chapter
etcetcetc

Let's start with a little comparison and usability shootout of the 10-year-old Word 2003 against the latest and greatest (and if you ask me, ugliest) Word version.

Word 2003 vs 2013

The Styles and Formatting toolbar offered only these formats in Word 2003 when a new document was created:

So far, nothing is easier or better than with Word 2013 there. No heading numbers indicated, no visible structure. Maybe WYSIWYG but who knows. Even if so, it does not look like what we want to achieve. Besides offering more styles right from the start, Word 2013 is similar:

To make the chapter numbers part of the chapter headings, you would typically adjust the Heading 1 style as follows:

In the Bullets and Numbering subdialog, the Outline Numbered (sic) tab is used to create outline numbering as desired. Applying any of these formats there would immediately adjust the styles for the other Heading styles 2 thru 9, resulting in this:

Done. That's it. You are now ready to go for the content. Slight adjustments to the formats might be needed though, yet Word did most of the work generating the outline numbers for all heading quite well.

People wo didn't visit a training will most certainly fail trying to do the same with Word 2007 and later versions. The problem is that with Word 2007 the dialog was drastically reduced:

So the Outline Numbered and List Styles tabs are no longer part of the Numbering and Bullets dialog. No visible clue as to where they have gone. "What the hell" you might think, "how do I get an outline numbering done now?"

New since 2007

Microsoft introduced the Ribbons in 2007, creating the first really fundamental change in how Office is used. While many buttons and icons looked familiar, they also added the all-new Multilevel List button as part of the Paragraph group in the Home ribbon tab:

Actually, things are easy if you are starting with a minimal document and take the time to create the structure first, then the content. Suppose we have a document like this:

It is always good to have the Navigation pane visible (at least from time to time) to verify that Word "understood" your outline structure properly. Only if this tree view is a tree and has the structure according to the document as you intended, things are good. Otherwise there is work left to do.

Good and Bad Choices

Clicking the magic new button will reveal a menu like this:

Note that the red and yellow highlighting was added by me. This is to indicate good and bad choices.
When you look for an outline structure in your headings, the suggestion marked red will meet the eye first and look promising - but is one of the worst choices you can make. This is what happens if you use it:

Not quite the expected, or is it? While an outline number was added to the level-1 line which was marked before assigning the multilevel list, the Heading 1 style did not change (see preview on the gallery button in the ribbon area). It does not contain the outline numbers now, nor did the Level 1 (D) line change even though it is a heading on the same outline level. What you did just modified the single line you selected, but users probably expected this to apply for all lines of the same nature. This is where most people start shaking their heads but need to go on somehow...
... usually by selecting the level-2 line and assigning the same multi-value list style to the line, resulting in this:

Again, the Heading 2 style was not adjusted, nor was the Level 2 (E) line which is on the same level, and even worse, the numbering does not start with 1 on the new level! Word just continues the numbering across different levels now instead of restarting it for each.
The reason for this is that the outline level and the heading level are detached. You can assign a different outline level to the line now:

But this is another false friend! The outcome looks better but still has issues:

While the numbering seems to be okay for now, again this did not synchronize into the Heading styles, so it won't affect other level-2 headings. The indentation applied to 1.1. Level 2 (B) is created just-in-time by Word and is not persisted in the Heading 2 either. If you don't like the indentation, you can adjust it, but you will have to repeat this for all Heading 2 lines in your document. Certainly not the way of choice.
No need to cry yet, there is a solution. Remember the popup shown before? Let's use the item highlighted in yellow this time:

Since I know what it does it is the one I prefer for my documents. The fine difference between the two is that the top one does not include the Heading styles. This is suggested by the text "Heading 1", "Heading 2", etc. in the lower (yellow) image. Note that these text fragments are missing in the "red" button. This small clue means the styles will be included in the outline numbering pattern . If it is missing, that means the format chosen will not be reflected into the styles gallery but happen once for the current selection. NOT wanted.
Using the item marked yellow causes the headings to synchronize to the outline structure which ends in the desired result you know from Word 2003:

Note the outline numbers now added to the Heading styles in the ribbon Styles gallery, and how all lines were properly adjusted. Watch the Navigation pane which also reflects the proper structure. Done, or rather, "wow" in Microsoft-speak.

The only problem is that besides the bad placement of a bad template above a good template in the Multilevel List popup, most people do not start this way, first arranging the headings and their formatting. Typically one writes down a rough structure which is only pre-formatted, then inserts text and does the formatting later - maybe not at the very end but some time later. If you are not prepared, this will cost you hours, or even days, when you least need it.

Misleader: List Numbering Button

You might intuitively hit the List Numbering button to outline your document because it may seem to be what you are looking for. It it not. This button's actual sole use is structured lists, as in step-by-step list, bullet list, any list that is no more than a block inside your document. But certainly not your document outline.
It is a bad choice when you accidentally use it for numbering your headings.

Suppose we move the cursor to the Level 1 (A) heading and click the Numbering button, the following is the outcome - note that the Heading 1 style does not adjust to containing the outline number. The other Heading styles do not change as well. So again your changes do not reflect into the respective style which you could easily miss.

While the result may appear to be good for now (because the first heading is now numbered), note that there is no more automatism supporting you. The other level-1 heading, Level 1 (D), is not adjusted accordingly, and the Heading styles are not changing.
Now what about the headings in deeper levels? It still looks like the goal could be achieved. Move to Level 2 (B), click the Numbering button again. Of course, Word will assign the outline number 2 to the line. Even though it is a different level, it does not detect that and continues level-1 numbering:

Digging around in the menus, you may come across the same Change List Level item shown in the Multilevel List pop-up menu above (near the bottom of the menu where I have marked the red and yellow buttons). The list level is 1 by default for all lines. If you assign Level 2 from here, this is the result:

The indentation indicates that we are creating a hierarchy by now, and that the Heading 2 and outline level 2 are in sync now. They are not.
Plus, there is no way to include the parent heading number here to achieve something like "1.a" instead of only "a.". It will always only be the number or letter or whatever you define that reflects the number of the chapter inside the current level. The paragraph formatting is applied by Word just-in-time and is not stored in the Heading 2 style, same as for the numbering itself. Both is "one-shot" if you take a close look at the styles in the ribbon. It is also not applied to the other headings of the same levels - see Level 2 (E) which keeps its formatting and is totally detached from what we just did?
While this has "WRONG WAY" written all over it, most people continue creating their document to come back to this later which is no less frustrating.

Rules

There is one general rule when it comes to headings: never use the Numbering button for anything else than actual lists. In other fields it is wrong to use it, it won't do what you expect, it will just guide you into chaos. Because even if what it does may look so, it has nothing to do with the structure of your document.
And even though you do need to use List styles to achieve proper outline formatting and structure, you must not use List-related functions to get there.
The key to proper outline numbering is using exclusively the Multilevel List button with headings. Word has no good support for it because whenever you move to a line that is a heading and was created using a Multilevel List, it is not the Multilevel List button that will become highlighted but rather the Numbering button left to it. What the hell, Microsoft? This points users in the totally wrong direction again.

More Control for Power Users

One clean way out of this is creating your own List style. This is like a style template you can create in the Styles toolbox:

Click the small "expand" button in the bottom right corner of the Styles ribbon group to extend the Styles toolbox. You can also press <Ctrl-Alt-Shift-S> to toggle the toolbox visibility. In the toolbox, click the New button in the bottom left corner.
In the Create New Style from Formatting dialog, select List as the Style type. Note the changes in the lower part of the dialog. To control how levels are presented, use the Format button in the bottom left corner, and select Numbering from the pop-up menu:
.



The Modify Multilevel list dialog opens up. Click More >> in the bottom left corner to expand it so all properties are shown:

Actually, this existed in Word 2003, too, but you never had to see it. Anyway it's a good thing to know how it works.
In the level list (top left), you select the level to be edited. The remaining dialog is about that selected item.
One thing is easily overlooked here: the Link level to style dropdown box on the right. If you want to have your headings numbered properly, it is totally recommended to assign the appropriate Heading style here:

This creates the missing link. You will have to repeat this for every level though...
Here I have assigned Heading 1 to level 1 and moved on to level 2, assigned Heading 2 to it and now let's see how we can get our outline number.

See how "Heading 1" and "Heading 2" have been added to the preview area? This is where we want to get. It indicates the link to the appropriate styles.
Note that you can enforce the use of arabic numbers over roman or alphabetic numbering by ticking the Legal style numbering checkbox indicated by the right arrow. It will disable the Number style for this level dropdown box.
The Include level number from: dropdown becomes available only from levels 2 and deeper. You can use this to determine the levels you would like to include in the outline number of your heading. Only the higher levels are available here, i.e. for level 2, you can only include level 1. For level 3, you would be able to include levels 1 and 2. The list will extend accordingly.
Another important switch here is the Restart list after: checkbox and dropdown. This is the trigger for resetting the level counter. While this is of no further use on level 1, you may want to continue a numbering across all chapters without being reset to 1 by a higher level heading that was inserted. This is where you need to go for this.

If you select that Level 1 item shown in the screenshot, the result is a little peculiar though because Word has not just added the level-1 chapter number to the left of the previous value without inserting a separator. What it actually shows you here is two separate fields so close together that they look like one:

It's up to you to separate them now, e.g. by inserting a "." or a space or whatever. If two levels are using the same number style, you will need to insert something between them. If number styles are differnt, it is still possible for readers to differentiate the levels (e.g. "1b" where 1 is the level-1 capter number and b is the level-2 heading). Just click into the text box, move the cursor between the segments and insert whatever you like. The grey background indicates the boundaries of each segment:

It's a pity that in this case it is impossible to tell what segment is what level, except counting from left to right yourself. Microsoft forgot to add any means of indicating that, with tooltips or on right-clicking. Nothing of that sort here, but it still works surprisingly good and mostly as expected because Word maintains the level order. If you are editing level 3 and add the level-1 number, it will guaranteed to be the very left segment, it is not just appended to the right of the existing expression. Same, if you insert the level-2 number, that will appear in the middle.
A small annoyance here is that you will have to repeat this as well for each level, and the number of "click dropdown - select level item - watch result - insert separator" operations increases by one for each.
Also watch the Number alignment dropdown because Word tends to mix left- and right-aligned.
At least Word will make life easier when it comes to indentations. If you'd like to have all headings on the very left with no indentation at all, click the Set for All Levels... button:

This is a real timesaver. Things offered here are pretty straight-forward. Unfortunately they did not include the Number alignment box here. Still a good function.

After you are done here defining your list, it might look something like this:

It is advisable to scroll through all levels and watch the detail fields change. It is a quick way to cross-check all settings. Click OK to submit the list.
Now how do we apply it? Click the Multilevel List again and note the new section inserted there

That is what we just created. In my opinion, the caption should not read List Styles but somehow indicate that these style are your own self-made ones. I'd prefer My List Styles or the like, alas, that's not going to change any time soon.
If you want to modify anything about your list styles later, here is a secret: right-click it and select Modify. Keep this in mind. It's virtually the only way to ever get back into that Modify Multilevel list dialog shown above!

You will see that this menu item is only available for the lists you created yourself. The built-in samples cannot be changed (what a shame).

Conclusion

You should be fine with the document you have now. The headings will now work as expected.

If you want to save some work, you can download the minimum sample document that served as demonstration material for this thread here.

Have fun! Hope this saves you all some valuable hours :)

And please excuse if my English is not quite to the point...I'm not a native English speaker, much less an expert in word processing terminology - yet. Any advice on possible improvements are absolutely welcome.

See you!