An e-mail education.

What you don't know about e-mail can, and will, hurt you.

   Neither snow nor rain nor gloom of night stays these couriers from the
   swift completion of their appointed rounds.

By the year 2001, the number of Americans using e-mail will total 135 million, according to one estimate. They will send 500 million messages each day. Some of them, no doubt, will be trial lawyers. And only a power outage stands in their way.

Few law firms today have no access to e-mail. Large offices sport elaborate systems, complete with scores of group addressees, instant communication with offices across the country, and hundreds of daily messages stuffing hundreds of in-boxes. Add external Internet access, and lawyers can communicate around the world. And communicate they do.

Lawyers, clients, cocounsel, and adversaries routinely correspond by e-mail. They transfer documents electronically so that motions, briefs, contracts, and other documents can trudge quickly through the tangled maze of "drafts" before reaching the nirvana of "final copy."

Hurling documents and messages electronically around the globe raises two vital concerns: netiquette and security. Netiquette should concern us because our correspondence, whether electronic or on paper, should be professional and direct. Security concerns us even more, and rightly so. How do we know someone isn't intercepting our e-mailed messages and documents? And how do we know that the sender is really the sender, the receiver really the receiver? We just can't shake hands and look each other in the eye in cyberspace. (At least not yet. Real-time visual contact, at affordable prices, will arrive soon.)

Don't miss manners As this form of virtually free communication has exploded over the past few years, a culture has arisen and, along with it, a rather elaborate code of conduct. To use the medium effectively, it pays to follow the code, often referred to as netiquette.

You should follow ordinary rules of written correspondence when deciding on the salutation in an e-mail. To a friend, "Dear John" does the job just fine. Or just "John." For business associates, "Dear John" is appropriate for those first-name-basis relationships. Again, "John" will suffice, too. You should follow all informal salutations with a comma. If the relationship is more formal, then "Dear Ms. Johnson" should begin your e-mail message. Follow these formal salutations with a colon. You need not include an inside address at all. Your return address should appear at the bottom, following your signature.

Right now, with standard e-mail programs, you have no effective way to make your signature unique. (That day is probably not far off, however.) To determine the close to your e-mail, simply distinguish between personal and formal e-mails. You can end personal e-mails any way you like: "Cheers," "Have a nice day," and "Good luck" all typically appear in e-mails these days. Follow this uplifting message with your first name. If you have to include your last name, you might review the appropriateness of your informal approach.

You should end a formal e-mail with your complete name, title, and firm. Some people "sign" their name by putting their common name above their formal name.

After personal or formal signatures, you should include an e-mail address, a telephone number, and a fax number. Do not rely on the "From" box to reveal your e-mail address.

   Your closing might look like this:

   Ed Good

   C. Edward Good

   Counsel & Writer-in-Residence

   Finnegan, Henderson, Farabow, Garrett & Dunner, L.L.P.

   [e-mail]

   202-408-4194 (office)

   202-408-4400 (fax)

Receiving a response to your e-mail can cause more frustration than most things in life. First, many response systems include the original message, each line preceded by ">" signs. Second, many responders will type their response below the original message, forcing the, uh, respondee to scroll forever just to find the beginning of the response. Third, many responders will bury responses within the text of the original message without highlighting the response in any way. (Be kind. Do not choose the third option.)

If you decide to include the original message, make certain your response begins at the top of the e-mail. You might decide to exclude the original message. Simply highlight it and hit the delete key. If the original message asked a spate of questions, then it's a good idea to include those questions in your response. But, for brevity's sake, include just the questions, not the entire message.

A tradition has grown up in cyberspace to use the ">" and "<" signs to indicate what someone else said. Thus, to answer an e-mail containing many questions, simply repeat enough of each to make clear the original question. Here's a question and a response:

   > Should we hire the Jackson firm to handle the defense? <

      Yes. Please set up an initial meeting for next Tuesday.

This message, of course, needs a response as well. You might need to respond by recreating the conversation. To show the various levels, use ">>" and "<<" for the original question and ">" and "<" for the answer to that question, and then respond. Like this:

   >> Should we hire the Jackson firm to handle the defense?<< (Your original
   question)

      > Yes. Please set up an initial meeting for next Tuesday.< (The answer)

      The meeting will begin at 9:30 a.m. in the east conference room. (Your
   response)

Make the format pleasing to the eye, at least by separating each part of the conversation by blank lines and excluding unnecessary parts of previous messages and responses.

Finally, when responding to e-mails, keep the "thread" intact. The "thread" is the link between e-mails and their responses, that is, the subject line of the response keeps the subject line of the original message. If the same conversation continues beyond three levels, you should reword the subject line to make clear the actual subject matter of the messages.

Indeed, if the original subject line does not inform, you should revise it to reveal the contents of your reply. Keep in mind that most people receive hundreds of e-mails each day, and helping them zero in on your message will ensure that they actually read it.

Looks count

The "look" of your e-mail must facilitate reading. It should not knock the reader up-side the head and say, "Want some real pain? Then try to read me!"

   Many e-mailers pay no attention to the appearance of e-mails. Anyone who
   has ever received an e-mail knows just how awful they can look and just how
   hard they are to read.

As the above visual disaster amply shows, the most irritating feature of many e-mail messages is the problem created by the way e-mail transmits your message. When you type in your e-mail "box" or "window," the text automatically "wraps" as you reach the end of each line. But the end of your typed line translates to a "hard return" when you click on "send." Then, when your recipients receive the e-mail, their left and right margins are probably not the same so that "wraps" occur at different places.

In the above example, the sender's margins produced a "wrap" after the word "appearance." Upon receipt, the receiver's e-mail system wrapped after the words "no attention to the." Your wrap at "appearance" is now a hard return in the receiver's system so that a new line forms. The result resembles a train wreck.

You can cure this problem in three ways: Use a larger font size, preferably size 12; make your box size smaller or your left-right margins wider (if your system allows this); or type hard returns after each line and make those lines relatively short.

Using hard returns holds the most promise for success. The above example might look like this:

   Many e-mailers pay no attention to the appearance of e-mails. Anyone who
   has ever received an e-mail knows just how awful they can look and just how
   hard they are to read.

Granted, the message will look narrow. But your reader won't be distracted by radically jagged margins.

For some reason, many people type e-mails the way they would never type anything else. Yet careful writers and professionals refrain from producing messages full of eyesores. One of the most irritating distractions is called "SHOUTING," WHICH IS TYPED BY SOMEONE PERMANENTLY LOCKED IN THE CAPS LOCKED POSITION.

Truth be known, many in the legal profession type e-mails with lots of caps. After all, we do it throughout legal writing. Witness the headings in briefs or the captions of motions, all typed for some inexplicable reason in ALL CAPS. Or consider the Uniform Commercial Code's insistence on displaying disclaimers of warranties in ALL CAPS. All this, despite considerable research showing the least effective way of emphasizing words is--you got it--ALL CAPS.

Thus, restrict the use of caps to one situation: when you absolutely need to emphasize some words (preferably just ONE word or PERHAPS TWO). In e-mail, you're stuck with caps as emphasis because many systems do not have bold or italic type. And even those that do don't necessarily produce bold or italics in the message received.

E-mailers should also refrain from excessively punctuating their messages. Multiple exclamation points at the end of a sentence should not substitute for quality of writing. Neither should excessive *s, #s, @s, and others.

Cyberspace culture

The culture of cyberspace has developed ways to express the full spectrum of human emotion. Instead of gloating, the e-mailer types a picture of a smiley face. Instead of grousing, the e-mailer types a frown. Obviously, these characters might properly show up in e-mails to close colleagues but not in official, professional correspondence. Newcomers to the culture, however, should learn the full inventory of emotions and their signals, or emoticons:

This Character        Means

:-) or :>)            happy

:-( or :<)            sad or angry

:-D                   shocked, surprised

:->                   sarcastic smile

:-|                   indifferent

:-/                   perplexed

:-e                   disappointed

;-)                   wink

;-}                   leer

:-@                   scream

:-O                   yell

8-)                   wears eyeglasses

:-Q                   smoker

:-*                   drinker

Frequenters of cyberspace have developed their own words and abbreviations, many originating on Internet chat boards. Inevitably, these stump the newbies. There's one. A "newbie" is a newcomer.

From the Internet, these expressions have migrated to e-mail, and it pays to know them. They, no doubt, will become accepted more and more, though caution says to get in the back of the line of those using them in formal correspondence.

This       Means This

BCNU       be seeing you

BTW        by the way

FWIW       for what it's worth

FYI        for your information

IMHO       in my humble opinion

LOL        laughing out loud

OBO        or best offer

ROTFL      rolling on the floor
           laughing

ROTFLOL    rolling on the floor
           laughing out loud

RTFM       read the funny manual

TNSTAAFL   there's no such thing
           as a free lunch

TTFN       ta ta for now

TTYL       talk to you later

BTW, it's not a good idea to close an e-mailed settlement offer with "ta ta for now."

Content counts, too

E-mailers, especially lawyer e-mailers, should resist the temptation to try out their skills as the next John Grisham. By its very nature, the medium of e-mail does a better job of rapidly sending information to others when messages are short and to the point.

Anyone with an overflowing electronic in-box knows how hard it is to wade through endless e-mails vying for elusive and never-to-be-granted literary awards. Once recipients make it through the clutter of not-so-funny humor and dire warnings of computer viruses that can take out entire cities, the last thing they need is a long-winded e-mail about a short, pithy subject. So keep it short.

One day historians will look back and peg the deterioration of the English language to three things: the decision to reduce the teaching of grammar in the public schools; television; and e-mail. Writers of e-mail messages seem to crank them out and hit the "send" button without much thought of grammatical accuracy and the correctness of punctuation and spelling. Certainly, the trial lawyer should treat e-mail correspondence the same as traditional correspondence.

In fact, you can reduce the probability of error by preparing the e-mail message in your standard word-processing system, running the spell checker, printing it out, and proofing it carefully. Then simply copy and paste the message in the e-mail window. As an added advantage of this approach, you can save the message in your word-processing system along with other correspondence to the same parties. Some of the more modern e-mail systems have a spell-checking capability. Certainly run it. But don't trust it.

Finally, resist the overwhelming urge to correct the grammar or spelling in an e-mail you receive. This is especially true of in-office e-mail. You should always follow your own standard of 100 percent accuracy, but I wouldn't impose it on others--unless, of course, you are a partner receiving from an associate an e-mail riddled with mistakes.

The advent of the Internet has radically changed the way people can transfer documents back and forth. (I transferred this article to TRIAL by e-mail.) By "attaching" a word-processed file, a sender can electronically forward to the recipient a document of virtually unlimited size. The receiving party can review it, revise it, and send it back. The original sender can review it, revise it, and send it back--until the parties both agree to the final version. This process often happens in litigation, of course, when more than one attorney or more than one law firm are involved in the representation of a single party.

Other than the question of security, discussed below, the biggest problem that e-mailers face involves the ability of the receiving party to "open" the attached file. If the party sending the document prepared it in WordPerfect and the party receiving it uses Microsoft Word, they might have difficulty exchanging the files. Often, they can get around these problems by "saving" the original document in the word-processing format used by the recipient. WordPerfect and Microsoft Word both have the feature of saving a document in the format of the competing word-processing system.

Security

The use of e-mail to transmit documents raises the most pressing concern of all: security. We could perhaps live with an invasion of our e-mail messages (assuming they didn't include sensitive information). But as lawyers we cannot allow prying eyes to see confidential work product. The question of security looms large.

E-mailers can achieve a low level of security through the use of word-processing passwords. Saving a document with a "password" keeps the document locked from anyone not knowing the password.

One problem with this approach, however, arises when the various parties exchanging the documents use different word-processing programs. If one party sends a document password-protected in WordPerfect to a user of Microsoft Word, the recipient cannot open the document, even if the received document is converted to Microsoft Word. The reverse holds true as well. To overcome this problem, the sending party should save the document in the receiving party's word-processing system and then password-protect it in that system. The receiving party can open the document by typing the correct password.

But this approach is fraught with danger. First of all, some 15-year-old computer hackers could probably slip unnoticed into your e-mail system or your network and sell your documents on the street corner. Second, when you send a document, how does the recipient know you are really you? Word-processing passwords just won't work. A much more impenetrable system must protect confidential legal documents and enable the receiver and the sender to identify one another. The answer lies in encryption.

For more than 20 years, scientists in the field of cryptography have used "digital signatures" to secure the contents of a document and to identify the sender and receiver. The system they developed relies on the use of "public keys" and "private keys." These security approaches are best described by example.

Suppose you must send documents to your cocounsel, and you want to do so privately. You also want to make certain that when you send a document, you can "sign" it so that your cocounsel knows you have read the exact document the cocounsel receives. You also want your cocounsel to be able to send you documents--privately and "signed."

As a first step, you must purchase some encryption software so that you can encrypt your document. Then, only someone with the right "key" can unlock the encryption and read the document. One of the most widely used systems of encryption is called PGP, which, ironically, means "Pretty Good Privacy." The name doesn't strike you as coming from some software that's very sure of itself, but, in the world of encryption, you'll find that every code can be broken--if the code breaker has enough time and resources. So "pretty good" means "excellent" or "foolproof" in the trade.

You first use PGP (or any other encryption software) to create two "keys," one called the "private key," the other the "public key." A key is a stream of characters that governs the exact way the document is encrypted. When you encrypt your document, you use the private key, which you must keep secret or your documents will not be secure. You then give the public key to your cocounsel or anyone else you correspond with. Holders of your public key can then decrypt your documents encrypted with your private key, and they can encrypt their own documents and securely send them to you for decryption with your private key.

Keys are called "bit" keys, that is, they will be classified as a 16-bit key, a 32-bit key, a 64-bit key, and so on exponentially. The more bits, the more difficult it would be to crack your encryption code, that is, to determine your private key.

If you have a 256-bit key, then the possible combinations of the characters in your key total 2 to the 256th power. Using the fastest computer known to exist today, a hacker would have to wait 30 years for the superfast computer to try all the possible combinations.

Applying all this encryption technology to e-mail security problems, a law firm could post its public key on its own Web site. Anyone wishing to receive documents from, or send documents to, this public-key holder would then have access to that public key. The law firm holding the public key also holds the private key. The law firm uses that private key to encrypt documents, which can then be decrypted by holders of the public key. Or the law firm uses the private key to decrypt documents encrypted by holders of the public key.

The private key serves a dual function. It provides virtually ironclad security and also acts as a private, unique signature, which identifies and verifies the sender of the document.

What's what

Public-key cryptography thus enables the receiver to identify the sender. But can the receiver rest assured that the content of the document has not changed, either through error of transmission or through subterfuge? To provide the important quality of data integrity, the e-mailing parties can combine public-key cryptography with what are called "one-way hash functions."

A hash function takes a digital stream of bits and converts it to a fixed-length byte or bytes known as a "hash-value," a "hash," or, in information-security guidelines, a "message digest." You can think of it as an electronic abbreviation of the document transmitted, kind of like a document head-note-in-bits. One-way hash functions work in only one direction; that is, the original message cannot be replicated from the message digest.

To generate a digital signature, the digital-signature computer program first generates a message digest of the text of the message. Next, the program encrypts the message digest using the sender's private key. (Some digital-signature schemes include a time-date stamp with the message digest before encryption.) The encrypted message digest serves as the digital signature. The digital signature is appended to the message and transmitted with the message to the recipient.

The recipient uses a computer program employing the same cryptographic algorithm to verify the digital signature. The program identifies the digital signature portion of the transmitted message. It then decrypts the encrypted message digest (and date-time stamp) using the sender's public key. The encryption program computes a message digest in the same way that the sender composed the message digest. If the message digest obtained by decrypting matches exactly the message digest computed by the recipient, two things are established.

First, the identity of the sender is authenticated because, as mentioned above, successful decryption using the sender's public key verifies that the message digest was encrypted using the sender's private key, which presumably is used only by the sender. Second, the message was not altered during transmission because the change in even one "bit" of the message would produce a message digest unlike the message digest encrypted by the sender.

Digital signatures are actually superior to handwritten ones because they authenticate every character of the attached message, not just the last or initialed page. Forgery, therefore, is next to impossible.

The next century will bring increasing reliance on electronic transmission of legal messages and legal documents. With encryption, the parties can relax in the knowledge that a computer hacker would have to lease the world's fastest computer for 30 years to unravel a 256-bit public-private key. Their security ensured, lawyers and clients will remember, not too fondly, the old days of waiting for "certified mail" or "personal delivery" before transacting their business.

Will the old saw about "lost in the mail" remain? Perhaps it will be replaced by some excuse targeted at the world of high technology. "The computer ate my service of process"?

C. Edward Good is counsel and writer-in-residence at the intellectual property firm of Finnegan, Henderson, Farabow, Garrett & Dunner in Washington, D.C.