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It really depends on how many sub-headings you have, and how much content is under each of those headings.

Your suggestion to put each sub-heading onto a separate page and to use tags to sort them into categories is probably a good one, particularly if you have a lot of content to store on the wiki.

However, if the existing Word document is only a couple of pages long it may be better to just store everything on the same page and to use the [[toc]] syntax to display headings at the top of the page.

You could then use the Edit Sections feature at the bottom of the page ("Options" > "Edit Sections") or the Edit Sections button ([[button edit-sections]]) to easily edit only a single heading at a time.

Welcome to Wikidot which is a great platform for building a knowledgebase. I have done this for several companies and the features that Wikidot provides really help to stucture and list your pages. But there are a few principles which you need to bear in mind which will help you enormously as your site grows.

1. Categories: It's not a good idea just to make hundreds of pages with no categorization and then rely on the search to uncover them. It's also not very user-friendly. The first thing you should do is to create categories. For example instead of having an hr page called benefits you could have a category called benefits and a page called health. The pagename would therefore be benefits:health. You could then add more pages in the benefits category, for example benefits:pension, benefits;gym, benefits:holidays. Later on in this post in the section on ListPages you will see how you can then list all the benefits pages.

2. Tags: As well as categories, a good knowledgebase should make use of tags to further help with searching and listing. So you might have pages called destination:australia and destination:south-africa and could add a tag of current to one but not the other. Then if you use a ListPages module you could ListPages in the destination category that are current.

3. ListPages: The ListPages module is a very powerful feature of Wikidot. In the paragraph on tags I mentioned listing destinations that are current. The syntax for that could look like this:

[[module ListPages category="destination"  tags="current" parent="destination:main" perPage="25" separate="false"]]
|| %%title_linked%% ||
[[/module]]

That would give you the list of all current destinations and a link to each page.

The documentation for the ListPages module is at http://www.wikidot.com/doc:listpages-module

4. You asked about how you can use the Heading Types to create a suitable index in the Content menu option on the left. You could use a Table of Contents (the syntax is [[toc]] although if you will have lots of pages that's not the best way to do it. It's probably better to do it manually by adding the main categories and perhaps some of the pages in them into your nav:side page. In that page you can also add buttons for creating new pages in the relevant categories. Have a look at a quick example of that at http://vineyard.wikidot.com/flyout:css (and the syntax for the menu entries is at http://vineyard.wikidot.com/flyout:nav). The permissions are relaxed so you can click on the page source button at the bottom of each of the pages to see the syntax.

5. If your knowledgebase pages are all going to have the same structure then you might want to consider using Dataforms which is similar to a database and allows you to set the way your users enter data. You can have dropdown lists, radio buttons, buttons to upload images while you are editing the page and so on. If yu make any change to the structure it is reflected across all pages instantly. The documentation for that is at http://www.wikidot.com/doc:data-forms

As you are a new user I'm sure that this all seems a lot to take in. But do continue to ask questions here on the forum and we will always be happy to provide assistance and solutions.

Thanks for the suggestions guys, very helpful and much appreciated!

Ian