I’ve been filling some gaps in my knowledge of Microsoft Word, and while browsing Word’s online “Help” database recently I was reminded of one of my favorite microtopics—“curly” and “straight” quotation marks and the role they play when you review contracts drafted by the other side to a transaction.
In a serif typeface such as Times New Roman, curly quotation marks (also known as “curved” or “smart” quotation marks) look like small figures six and nine with the enclosed portions filled in. (With sans serif typefaces, the look can vary; see for example the quotation marks in this post, which uses Verdana.) Straight quotation marks (also known as “dumb” quotation marks) point straight down. You can have double and single quotation marks, and single quotation marks do double duty as apostrophes. (For more on quotation marks, go to Wikipedia.)
Straight quotation marks were introduced on typewriters to reduce the number of keys on the keyboard, and they were retained for computer keyboards and character sets. But curly quotation marks are preferred in formal writing, so Microsoft Word provides an option under “AutoFormat As You Type” that allows you to replace straight quotation marks with curly quotation marks.
That option is set by default, with the result that unless you deselect it, as you type quotation marks and apostrophes they will automatically be changed from straight to curly. But if you import into a document (from another Word document, the SEC’s EDGAR database, or elsewhere) blocks of text containing straight quotation marks, unless you take further steps those straight quotation marks will remain straight. The converse can apply: if the “AutoFormat As You Type” option isn’t selected, you can introduce curly quotation marks into a document in which you’ve typed straight quotation marks.
What’s the significance of having both straight and curly quotation marks in a draft contract? It’s messy typographically, but that’s the least of it. When you send a contract to the other side for their review, you’d like them to get the impression that you prepared it using contracts that have formed the basis for many a deal. But mixing straight and curly quotation marks is a hallmark of the slightly sloppy scissor-and-paste job, and a savvy reviewer will pick up on that. When I see mixed straight and curly quotation marks, I smell blood in the water—I know that I can expect to encounter other, more significant problems.
Here’s how you fix mixed straight and curly quotation marks: You’ll want to make them all curly, given that curly quotation marks are preferred for formal writing. If when you type quotation marks they are straight, you need to select the option under “AutoFormat As You Type” that automatically turns your straight quotation marks into curly quotation marks as you type them. You can do that by choosing “Tools,” then “AutoCorrect Options,” then clicking on the “AutoFormat As You Type” tab and selecting the relevant box. (If your quotation marks are already curly, you know that this option has already been selected.) Then you find and replace all instances of double or single straight quotation marks with curly quotation marks: on the “Edit” menu, click “Replace,” and then in both the “Find what” and “Replace with” boxes type the double straight-quotation-marks symbol and then click “Replace All.” Then repeat this process with the single straight-quotation-mark symbol. Or vice-versa. That’s the simplest way to plug a small but telling chink in your drafting armor.