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Our office creates many documents with multilevel lists in them. Typically
these lists are a mix of headings and numbered paragraphs. They usually look
something like this:

1. Heading (bold, underline)[List level 1]
1.1 Heading (bold)[List level 2]
a. Paragraph (default styling)[List level 3]
i. List (default styling or no spacing)[List
level 4]

The number scheme is fairly consistent from document to document, but the
styling isn't. E.g. in another document list level 2 might be a paragraph and
level 3 might be a list with no spacing between paragraphs; or all four
levels may be headings and styled bold and underline.

The office used to have a style sheet that split each of these different
list elements up; there were separate sets of styles for numbered headings,
numbered paragraphs and for numbered lists.

The above example would have been created using styles from all three sets.
This was before my time (and before Word 2007) so I am not sure exactly how
it worked but apparently the three unlinked sets behaved as though they were
all part of one multilevel list. E.g. Level 2 would properly restart after
level 1.

Word 2007, however, broke this system.

I've tried to replace it with just one list style linked to the heading
styles. By default all the heading styles are default styling and if you want
something bold or underline you just make a quick change to the style.
Totally reasonable right?

But my boss hates this. He can't wrap his head around having to do a bit of
setup work for a list. He wants it back the old way. He is very insistent on
this. It's driving him crazy.

I've no idea how the old system worked. That it did at all makes no sense to
me. Does anyone have any idea? Your insight would be much appreciated. I'm
not crazy telling him that it's impossible am I?