The 5 Most User-Hostile Microsoft Word Features

Even though I have been a defender of Microsoft Word for years (even when faced by die-hard WordPerfect users), even I have to admit that some of Word’s features just make no sense. Unfortunately, some user-hostile features are the ones most likely to be used in a law office. Here are my nominations for the most frustrating, user-hostile Microsoft Word features.

Table of Authorities

If you have to do appellate briefs that require a Table of Authorities, you have my sincerest sympathies. No matter how carefully someone marks their citations, something goes wonky with the Table of Authorities: the indentations are not right, there is not enough space between the entries, the font does not match the text of brief . . . the list of what can go wrong is nearly endless. If it is a simple brief, the temptation is to do it all manually. I can not say that I blame anyone for that.

If you think marking citations looks confusing, wait until you generate the Table of Authorities. If you do TOAs often, you can buy software that can step between you and Word and provide an easier experience. But it will cost you.

Bullets and Numbering

Frankly, I can understand why a Table of Authorities is a difficult thing to automate. There are a lot of pieces that have to fit together just so. But what is so freaking complicated about having auto-numbered paragraphs that are indented (or not) correctly? The whole thing becomes a tangled mess of field codes, Styles, and paragraph formatting, and if your numbering ever gets off-track, heaven help you.

Bullets and Numbering is a confusing mess of Styles. Deviate from the built-in ones, and you’re in trouble.

Yes, there is help to be had here too, but again, it will cost you. At the very least, you will want to turn off the feature that lets Word AutoFormat anything that looks like it ought to be a bullet or paragraph number. Then, you can always do things manually until you choose not to.

Track Changes

I would be hard-pressed to name a single legal practice specialty that does not need this feature. And truthfully, just turning it on and letting it mark the text as you type is actually quite simple. It’s trying to deal with the text later that’s complicated. Do you want to print the changes, or do you want to print the document as if all the changes have been accepted, or do you want to print the document as it was originally? Well, you can do all that, but first you have to figure out the difference between Final Show Markup, Final, Original Show Markup, and Original. It is not nearly as intuitive as it sounds. And if you got balloons but you don’t want balloons, or vice versa, good luck finding the place where you suppress or add them.

Do your eyes roll back in your head when you see this? I know mine do.

Do your eyes roll back in your head when you see this? I know mine do.

You might be better off simply using the Compare feature to look at the differences between two distinct drafts.

Trust me, Compare is a lot simpler. And safer.

Trust me, Compare is a lot simpler. And safer.

Making Forms

From client intake to going to trial (or whatever your practice’s endgame is), forms could be a huge timesaver. And although Microsoft Word has a pretty impressive database of templates, they’re really not geared to law offices.

If there were world enough and time, you could assemble your own set of forms. But between hiding the Bookmark and Cross-Reference feature on the Insert tab and squirreling away the Controls feature on the hidden by default Developer tab, it’s almost as if Microsoft is telling you, “don’t bother.” Even Adobe does a better job of this sort of thing that Microsoft.

There's a reason this is called the Developer tab. Fortunately, it's not displayed by default.

There’s a reason this is called the Developer tab. Fortunately, it’s not displayed by default.

If you are a Microsoft Word user determined to streamline your document production process with forms, you can get help here, too, and a lot cheaper than you think. You can check out a simplified version of TheFormTool for free, or you can pay a small fee for a premium version that does really cool things like convert $123.45 to its text equivalent of “One Hundred Twenty-Three and 45/100ths Dollars” plus calculate amounts and dates. With that and a little elbow grease, you can save yourself the frustration of learning the Cross References feature and leave the Developer tab for the propeller heads.


Want to paste text from one document to another? Sure, you can do that, and the safe bet is you’ll somehow screw up the formatting in your destination document in the process. That’s because Word tries to figure out whether you wanted to paste just the text or some (or all) of the formatting.

How many ways can you paste text? Too many.

As if that is not complicated enough, there are settings embedded deep in the Options area that control the defaults for pasting text within the same document, between Word documents, and from another program into Word. After all, getting text from one place to another isn’t all that simple (but it should be).

Your Nominees?

Of course, these are just my pet peeves. Every Word user has their own “it’s got a be simpler than this” feature. What’s yours?

Originally published 2013-09-19. Last updated 2015-07-24.

Featured image: “Angry businessman holding hammer over laptop in his office” from Shutterstock.


  1. Avatar Sam Glover says:

    Spot on. I rarely open Word any more, unless I absolutely have to. It’s much easier to write in text (I prefer Markdown), so that I don’t have to worry about formatting. Or Google Docs, which mostly (blessedly) limits formatting options, mostly for the better.

    Tracking revisions is, however, user-unfriendly in every software product I have used. The best I’ve encountered so far is probably the online text editor, Editorially (which I’m in love with, in general), but text is obviously much less complicated than a typical legal document.

    As for bullets and numbering, I’ve actually learned to live with it. I prefer the way LibreOffice handles lists, but I can work with Word just fine. It’s taken years to get to this point, however, and I still screw it up now and then.

    • Avatar MLSandler says:

      Track Changes is intended to work as a cycle. If you don’t use it the way intended, you get frustrated. Turn it on, everyone had their portion, the “owner” of the document decides which changes stay and which changes go, then you turn tracking OFF, THEN you have your executable document. Otherwise it can be very embarrassing.

  2. Avatar Socialated says:

    I think track changes, bullets and numbering, pasting are all great features. I don’t use TOA. Microsoft has to deliver on all the details to make it all encompassing. Certain features might not be user friendly, but it get’s the job done as the world’s best word processor.

  3. Avatar Cindy Wolf says:

    You’ve hit my list with one more. WHY did they move all the functions around? And who thought that adding a click for a tab at the top to get a new ribbon and then another drop down menu was easier than the prior GUI? Why do we need to continually choose New and then Document instead of Blog Post to start a new doc? Seriously? Office types use Word. Freelance bloggers use OO or something free.

  4. Avatar Leung WC says:

    Multi-column text

    The multi-column features REQUIRES creating separate section in a documents. This completely screw up the following features:

    1. Sections: There is simply NO WAY to count the sections numbers correctly with multi-column text.
    2. Page layout: Different sections uses different layout such as page size, orientation, headers and footers, and page numbers. Having multi-column text REQUIRING sections to be created, and each section doesn’t share the same page layout. The worst cases is having 3 or more sections in the same page. There is no way to identify and/or fix the broken page header/footer/numbers in the 2nd section without adding a manual page break.

  5. Avatar Kris N says:

    Why is it so hard to leave a page number off of the first page?!?!?

    • Avatar legalofficeguru says:

      If you embed the page number into the header or footer (instead of using Insert | Page Number), it’s actually a lot easier. Then, you can double-click into your header or footer, go to the Header/Footer tab that pops up, and check the box “Different first page” in the Options section.

  6. I’m not sure anyone would label this as “user-hostile,” but it’s hard to underestimate the damage Word has done to mankind by its choices of default fonts, first Times New Roman and now Calibri.

  7. Avatar Faithful says:

    How do I set default auto numbering and bullets, so that the left bit is at 0, and the indent is at 1, please? I can’t find an article on the subject.

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