Flash forward to now, or rather yesterday. I had occasion to revisit Typography for Lawyers, a handsome and informative site maintained by Matthew Butterick, a solo litigator based in Los Angeles. (I’ve corresponded briefly with Matthew.) On this page of the site, I read the following:

Avoid using the core operating system fonts in printed documents.

On Windows, that includes Arial, Calibri, Cambria, Candara, Comic Sans, Constantia, Courier, Georgia, Helvetica, any flavor of Lucida, Palatino, Trebuchet, and Verdana. On the Mac, that includes Arial, Courier, Helvetica, Palatino, Skia, and Verdana. Subject to a few exceptions, you should also avoid Times New Roman.

Operating system typefaces have three problems:

1. They’re overexposed. The fact that they’re included with the operating system for free means that people who are lazy and cheap tend to use them. You don’t want to be lumped in with those people.
2. They’re not very good. This is less a problem on the Mac. But certain typefaces included with Windows are among the most god-awful on the planet. I don’t want to name names, but my least favorite rhymes with Barial.
3. They’re optimized for screen display, not printing. The Mac and Windows system fonts have been meticulously engineered to look good on screen (for instance, website text). But often, that means that subtle design details have been sanded off, and the typeface looks clunky on the printed page (e.g. Georgia).

Here’s my take on these matters:

• I don’t care that Calibri is overexposed. In fact, that’s an asset. When I send someone a draft, I don’t want them to be unnecessarily distracted by the typeface. And I certainly don’t want my contract to be displayed on their system in a fallback typeface because their system didn’t recognize my exotic typeface.
• I’m not going to claim that Calibri is king among typefaces. All that matters to me is that I find it a big improvement over Times New Roman and Arial, the typefaces almost invariably used for contracts before Calibri came on the scene. And more to the point, my informal research and discussions suggest that typography professionals broadly agree with me.
• I do an inordinate amount of my reading on screen, and I suspect the same applies to transactional lawyers generally. So it makes sense for me to use, for my benefit and for the benefit of anyone else who’ll be reading my document on screen, a typeface designed to read well on screen. Calibri is one such typeface. And it would be inconceivable to use one typeface for reading a document on screen and another when you print it out.

More generally, Matthew’s typeface needs differ from mine because he’s a litigator and I’m a transactional lawyer. His writing seeks to persuade; mine regulates conduct and is akin to software code. And he submits finished documents to courts or to opposing counsel; transactional lawyers send drafts to lawyers on the other side of the deal, and they want to be able to make changes or mark comments and send them back.

The net effect of those differences is that any if any transactional lawyer were to use for a given contract Sabon, Goudy Old Style, or any other typeface recommended by Matthew, others working on the transaction would, I suspect, be baffled.

So I’m sticking with Calibri.

[Update April 22, 2010: Matthew kindly pointed out to me that on this page of his site he acknowledges that if you're sharing drafts of a document, you'd be best off using an operating system font. My apologies to Matthew for not having noticed that.

And Bob's comment below reminded me that I could afford to be less one-size-fits-all in how I use typefaces. One reason I like Calibri for contracts is that it isn't assertive; as such, it's in keeping with contract prose, which shouldn't have a voice. But just as other kinds of prose differ from contract prose, typefaces other than Calibri might well work better for other kinds of documents. It so happens that I have little room for experimenting, as documents for on-screen reading and drafts for sharing account for the vast majority of my output. But perhaps at some point I'll take for a spin some of the typefaces that Matthew recommends.

So I feel a little sheepish that although at origin this post was intended to highlight how Matthew's recommendations didn't apply to my needs, it turns out that I'm left with nothing to disagree about! But speaking selfishly, the most interesting posts are those where I end up in a slightly different place than where I started.]

A reminder: When it comes to matters of typography, people like what they’re used to. So your reaction to a given typeface is perhaps less relevant than your reaction after having considered the opinions of typography professionals. For example, studies have cast doubt on the assumption that serif typefaces are easier to read than sans-serif typefaces, so I have no qualms about recommending Calibri.

When you’re looking to shift entrenched positions, repetition can be helpful. So if you’re not convinced of the righteousness of ragged right, I suggest you check out this post on slaw.ca by Simon Fodden. (I learned about it from Ray Ward.)

Simon takes the opportunity to point out that it would be best to use one space, not two, after punctuation. So say all typography authorities I’ve consulted; I discuss that too in chapter 15 of MSCD and in this October 2006 blog post.

In all things relating to typography, bear in mind that people like what they’re used to. So if you’re inclined to fight tooth-and-nail for full justification and two spaces after punctuation, bear in mind that your own habits are less relevant than the views of typography professionals.

And bear in mind also that these habits are not hard to break. Once you make the change, you realize that the sky hasn’t fallen and that, in fact, life is a little simpler.

The gist of it is that Texas courts have ruled that an indemnity provision that requires Party A to indemnify Party B for Party B’s own negligence is unenforceable unless (1) the contract is explicit that the indemnification covers the negligence of the indemnitee and (2) the provision in question is conspicuous.

In Dresser Indus., Inc. v. Page Petroleum, Inc., 853 S.W.2d 505, 509-11 (Tex. 1993), the Texas Supreme Court applied to the express negligence rule the Uniform Commerical Code’s standard for conspicuousness. As explained in MSCD 15.37 and in this February 2008 blog post, for something to be conspicuous under the UCC it doesn’t need to be in all capitals, so it follows that the same applies for purposes of the express negligence rule under Texas law. And using some other form of emphasis, such as bold italics, would make the provision conspicuous yet much easier to read.

The most accessible article I’ve seen on the conspicuousness requirement of the Texas express negligence rule is this one, written by Randy King, a partner at Porter & Hedges. The article was published in 2002, and there’s been some caselaw since then, but nothing that changes the basic conspicuousness analysis. A quick source of more recent caselaw is a Baylor Law Review article at 60 Baylor L. Rev. 941.

When he mentioned the Texas conspicuousness requirement in this morning’s seminar, David Miller recalled how he once found himself working on a transaction involving a Texas company. A Texas law firm had been called on to give an opinion, but they were nervous about whether a given indemnification provision—evidently one aimed at satisfying the express negligence rule—was sufficiently conspicuous. Demonstrating the expediency that is the stock in trade of the transactional lawyer, those gathered in the conference room solved this problem by using a fluourescent marker to highlight the provision  in the copies to be signed …

The Legal Frontier post is about how use of all capitals makes contract text harder to read. That wouldn’t come as a surprise to anyone who pays the slightest attention to typography, but it bears repeating, as all capitals remains in widespread use among contract drafters. I particularly liked Andrew’s practice of using Word’s “change case” function to change all capitals when he’s reading a contract on screen.

If you’re using all caps for anything other than article headings and party names in the introductory clause and signature blocks, you might want to reconsider. I use instead bold italics. If that doesn’t make text conspicuous enough for you, put a box around it.

But here’s my question: Andrew says that some laws require that certain provisions be written in all capitals. Can anyone cite for me any such laws?

And no, the Uniform Commercial Code doesn’t count. Parts of the U.C.C. require that text be “conspicuous.” For example, section 2-316(2) states that a disclaimer of the implied warranty of merchantability must be conspicuous. But section 1-201(10) of the U.C.C. specifies that “language in the body of a form is ‘conspicuous’ if it is in larger or other contrasting type or color”; it doesn’t say anthing about all capitals.

And Amercian General Finance, Inc. v. Bassett, 285 F.3d 882 (9th Cir. 2002), debunked the notion that text needs to be in all caps to be conspicuous. I particularly like this sentence from that case: “Lawyers who think their caps lock keys are instant ‘make conspicuous’ buttons are deluded.”

Incidentally, I’m not sure that conspicuousness and readability are the same thing. You can make a particular provision catch the eye, for instance by using all capitals, but at the same time make it hard to read once readers focus their attention on it.

But here’s a related question: I’ve previously used underlining to emphasize section headings, each defined term when it’s being defined, and references to exhibits and schedules. (See MSCD 12.9.) Should I use bold in all those instances, or is there anything that I should stop emphasizing?

For one thing, a reader has suggested to me that using quotation marks around a defined term when it’s being defined (see MSCD 6.14, 6.23) by itself constitutes a form of emphasis, and that adding bold would be overkill

Also, up till now I’ve emphasized references to exhibits and schedules, the idea being that doing so makes it easier to keep track of attachments. Is that a usage worth retaining? (Incidentally, that emphasis is the only reason I use initial capitals in references to exhibits and schedules. Without emphasis, there would be no reason not to treat them like section references. See MSCD 13.33.)

Such are the gripping issues I’ll need to resolve as I work on MSCD2. I welcome your suggestions.

Underlining—or rather underscoring, to use typographer terminology—is a typewriter convention created to approximate common typographic effects that couldn’t be achieved with a typewriter. Typographers don’t like it. James Felici, The Complete Manual of Typography (2003), notes that in word-processing programs underscoring is too close to the baseline, causing it to overlap descending letters. It says that the effect is “not pretty, and you should avoid using it.”

Nevertheless, I’ve been reluctant to use the obvious alternatives, namely bold or italics. In MSCD 12.15, I say “Do not use boldface: it is too emphatic and makes words leap off the page. And do not use italics, except perhaps in amendments, as noted in 14.20: it is too subtle.”

But this has nagged at me, so once I decided that I like Calibri (for more on that, see today’s post on typefaces), it made sense for me to see what bold text looked liked compared to underscored text. And lo and behold—I liked the bold Calibri.

So not only am I proposing to dump Times New Roman and Arial in favor of Calibri, I’m also proposing to use bold type instead of underscoring. Sorry for pulling a switcheroo on you.

In terms of a reason for my change of heart, it may be that my aversion to bold text was simply a function of my aversion to Times New Roman. But also, Simon Daniels, the program manager of Microsoft’s typography group whom I consulted regarding typefaces, mentioned that some fonts, when tuned for the screen, look extra bold. With ClearType (discussed in today’s post on typefaces) you avoid that problem.

Note that I still prefer bold to italics for emphasizing contract text.

In any event, here’s the cumulative effect of today’s typography convulsions: click here to see a PDF of a sample page of a contract using Times New Roman and underscored text; click to here see a PDF of the same page using Calibri and bold text.

Brace yourselves—I’m proposing a change of typeface.

The Current Regime

I suggested in this November 2006 post that Times New Roman isn’t a thing of beauty.

And I’m not crazy about Arial either, at least not for purposes of business documents. And not at 10 point, the main advantage of which seems to be that one can cram more words onto a page. (For some background on Arial, see this discussion by the graphic designer Mark Simonson; he describes Arial as “rather homely.”)

But it has come to pass that liberal-arts types flock to Times New Roman and technical types cling to Arial—a trivial manifestation of the “two cultures.” That Times New Roman is so prevalent is due to its having been the default typeface in Windows from version 3.1 until Vista and in Word until Word 2007.

As for alternatives, the comments to my post on Times New Roman suggest Palatino, Garamond, Century Schoolbook, Futura Book, Bookman Old Style … . Whatever the aesthetic merits of these and other out-of-the-mainstream typefaces, they’d represent an idiosyncratic choice. And business contracts aren’t conducive to idiosyncracy.

The Prospect of Change

In my post on Times New Roman I said that I planned on changing typefaces, and I suggested as possible candidates the ClearType Font Collection, which is the new suite of typefaces included with the Microsoft Vista operating system and the Microsoft Office 2007 suite of applications. Now that Vista and Office 2007 have been with us for a few months, I finally decided to resume my hunt.

With that in mind, I was lucky enough to have the opportunity to pick the brains of two people at Microsoft—Tanya Moore, senior director of IP licensing, and Simon Daniels, a program manager in Microsoft’s typography group. To the extent that I’ve been able to make sense of this issue, I have them to thank.

ClearType

The impetus behind the new typefaces is Microsoft’s ClearType technology. Here’s how Microsoft describes ClearType:

ClearType is a software technology developed by Microsoft that improves the readability of text on existing LCDs (Liquid Crystal Displays), such as laptop screens, Pocket PC screens and flat panel monitors. With ClearType font technology, the words on your computer screen look almost as sharp and clear as those printed on a piece of paper.

ClearType works by accessing the individual vertical color stripe elements in every pixel of an LCD screen. Before ClearType, the smallest level of detail that a computer could display was a single pixel, but with ClearType running on an LCD monitor, we can now display features of text as small as a fraction of a pixel in width. The extra resolution increases the sharpness of the tiny details in text display, making it much easier to read over long durations.

To help spread the word about the new typefaces, Microsoft produced a book entitled Now Read This: The Microsoft ClearType Font Collection. It explains how ClearType led to the new typefaces:

In the course of our work on ClearType and creating new typefaces for electronic books, we realized that the unique knowledge we have could be used to design new typefaces which took advantage of the way ClearType works.

We are committed to excellence. So it was obvious that if we wanted to create new ClearType-optimized typefaces, we should work with the best designers in the world. We asked type designers to submit draft designs to be judged competitively; we commissioned complete designs and then built computer fonds using the highest-quality technology we had—ClearType has evolved a great deal since we invented it in 1998.

The new Western fonts in this book are the result of that project.

Is ClearType worth the fuss? Now Read This cites a recent study that concluded that reading ClearType was, on average, slightly more than 5% faster than reading without ClearType. That might seem like a modest difference, but cumulatively it would have a substantial effect, particularly as a drafter is likely to read a given draft much more on screen than on paper.

The ClearType Font Collection

Here are the new typefaces:

• Constantia (serif)
• Cambria (serif)
• Corbel (sans-serif)
• Candara (sans-serif)
• Calibri (sans-serif)
• Consolas (monospace)

This Poynter Online article provides a convenient overview. Calibri has been designated the default for body text in Office 2007, and Cambria has been designated the default heading typeface.

Aesthetic Considerations

First, let’s consider the aesthetics. Given the resources that Microsoft has devoted to the new typefaces—Now Read This says that Bill Gates has made improving reading on the screen one of his personal “Top 5″ priorities—I’m not surprised that I found them all to be attractive.

Of the serif typefaces, for purposes of business documents I have a slight preference for Cambria, as being more formal.

But the sans-serif typefaces were the real revelation. I found them all more agreeable than Arial, but the one that particularly caught my eye is Calibri, which is distinguished by its rounded ends. Generally, it could be described as a “humanist” sans-serif, in that it offers some variation in line width and so should be more readable than more severe sans-serif fonts. I found that label appropriate, in the way it suggests a mix of what draws technical types to Arial and liberal-arts types to Times New Roman. To my surprise, I’d be happy offering Calibri to both groups. It’s what I’d like to switch to.

But see for yourselves: click here to see a PDF of a sample page of a contract using 12-point Times New Roman; click here to see a PDF of the same page using 11-point Calibri. I used 11-point Calibri because that’s Word 2007′s default font.

(Note that Calibri in a PDF document is nowhere near as clear on screen as Calibri in a Word document with ClearType. Also, note that the Times New Roman document uses underscore for emphasis whereas the Calibri document uses bold; for more on that, see today’s other post.)

One feature of Calibri might make it more palatable to drafters than the other new sans-serif typefaces—as a default, it uses lining numerals rather than old-style numerals. (Click here for a comparison of lining numerals and old-style numerals.) For one thing, users of Times New Roman and Arial would be used to lining numerals. And although old-style numerals blend well with lowercase letters, in contracts you generally want numbers—whether used to state amounts or used to enumerate blocks of text—to stand out.

Space Considerations

Of the two sample pages that I link to above, the version with Calibri squeezes a couple more lines on the one page than does the Times New Roman version. If both versions used 12 point, the Times New Roman version would be the one fit a couple more lines on the page. That’s because, in typographer speak, Calibri has a slightly larger x-height, wider letter-spacing, and more in-built interline spacing (also known as leading).

I may tinker with Calibri’s size, to see if I prefer 12 point. But for the sake of simplicity, and in order not to scare off anyone who doesn’t like the idea of changing to a font that takes up more space, for the moment I’m happy sticking Word 2007′s default, 11-point Calibri.

Compatibility with Word 2003

The notion of changing typefaces raises the issue of cross-platform font compatibility.

My first question in that regard was whether only those who’d installed Office 2007 would be able to use the new typefaces. That’s not the case—I realized that although I haven’t yet installed Office 2007, the new typefaces were available to me in Word 2003. That’s because I’d installed the Microsoft Office compability pack for Word, Excel, and PowerPoint 2007 file formats. Anyone using older versions of Word or even a competing word-processing program can do so too, in only a few clicks.

Mac Compatibility

A less tractable issue is compatibility with Macs. If you send a Mac user a document that containing any of the new typefaces, they’d be able to open it, but it would probably display in a fall-back font such as Lucida Grande. That by itself would be a nuisance, as it would interfere with, for instance, exchanging signature pages. Furthermore, it would complicate negotiations, as the line breaks and page breaks in the recipient’s version would likely be different from those in the sender’s version.

Here’s my take on this: Macs have only a toehold at law firms. (Click here to read a recent Lawyers Weekly article about this.) So the life-enhancing quality of working with a classy typeface that’s designed to work with ClearType far outweighs the inconvenience of having to switch back to Times New Roman or Arial on those rare occasions when you’re dealing with a Mac user.

And a couple of factors could turn this from a minor issue to a non-issue. First, the Mac user you’re corresponding with might have elected to run Windows as well as the Mac operating system. And second, the upcoming 2008 versions of Mac Office will likely resolve this issue.

Printer Speed

Times typefaces are embedded in laser printers. That makes for quicker printout, as you don’t need to download Times New Roman to your printer each time you print a document.

In theory, that means that if a large organization were to switch all at once to one of the new typefaces, users might notice a drop in printer speed.

But with the speeds offered by current hardware, this is less of an issue than it once might have been. And I gather that discussions are ongoing regarding licensing the new typefaces to printer manufacturers. That would resolve the issue entirely.

Weighing Change

So in favor changing to Calibri (or, if you prefer, one of the other new typefaces) you have aesthetics and the fact that unlike Times New Roman and Arial, it was designed to work with ClearType. In favor of standing pat you have trivial cross-platform compatibility issues and … inertia. Sounds familiar.

I would remind those inclined to cling to Times New Roman that its current prevalence has nothing to do with its inherent qualities. Instead, it has everything to do with decisions made at pivotal moments in the recent past by companies responsible for developing our reading and writing technologies.

Similar factors favor a more worthy candidate, Calibri. Seeing as it’s one of the default typefaces for Office 2007, opting for it couldn’t be considered a nonconformist decision.

Furthermore, changing typeface would be a lot easier than changing contract language, in that the other side would have no basis for objecting to the change. And within any given firm, the change wouldn’t have to be made lockstep—any lawyer could make the change whenever he or she has the urge.

But I won’t do anything irrevocable—such as asking Payne Consulting Group to revise the MSCD options in the Numbering Assistant—until I’ve digested any feedback I receive.