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.