Electronic Mail and Lawyering

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Electronic Mail and Lawyering: Better Safe Than Sorry

By: Alan S. Goldberg

The use of Internet electronic mail among lawyers is mushrooming. While training classes on the use of this feature are helpful, the unique nature of a lawyer’s professional obligations warrants advice regarding special risks and special concerns. Here are some thoughts and ideas that should be borne in mind when using e-mail:

1 · E-mail is a communication. -- Just like a letter, a fax memo or a phone call from someone in your law firm, e-mail is an communication that presents your law firm to the community. Extra care is appropriate when authoring e-mail, because of the tendency of some to be more aggressive or even offensive when using it. It is all too easy to create e-mail -- perhaps while under stress or during a moment of anger -- that under normal circumstances would be torn up after being read in draft paper form but which is immediately sent electronically because of the ease with which e-mail can be transmitted and the absence of a cooling-off period between dictation and editing.

2 · Communications are to be saved. -- Most lawyers save file copies of correspondence and fax communications. The same procedure should be used for Internet electronic mail: Most e-mail received from outside of a law firm should be printed and filed. Most e-mail being sent to someone outside should be printed, in order to have a file copy available. If you send an e-mail message while using online remote access (that is, while you are out of your office but connected by a computer telephone hook-up to your office computer network), a file copy should also be made by printing a copy of the e-mail in your office from your computer for later filing.

Bear in mind that only an e-mail sent through online remote access will be saved on your office personal computer; e-mail sent using a computer you use outside of your office will not be saved on your office network for printing purposes. An alternative is to send a duplicate of any e-mail that you send from out of your office to your own office Internet e-mail address, so that you will have a copy in your office for printing and filing.

3 · Proofreading is particularly important. -- Scientific studies have shown that proofreading prowess drops significantly when the communication being proofread appears on a video monitor instead of on paper. Thus e-mail should first be printed in draft form; proofread; and corrected as appropriate before being sent. This should be an absolute and unconditional rule, given the fact that even a misplaced comma or one word inadvertently omitted could cause a fatal error. Remember that evidentiary rules generally will permit efforts to introduce e-mail in evidence.

4 · Reliability is not total -- Unlike general assumptions universally made regarding the U.S. mail, courier express services and faxing, in general e-mail is not yet viewed as being sent via a communication technology entitled to a presumption of timely and proper delivery. To the contrary, because computers sometimes break down and do odd things and people sometimes either don’t turn their computers on or don’t know how to make them work properly, Internet electronic mail won’t always get to where you think it will. A good practice to follow is to request, in the e-mail, that the intended recipient acknowledge receipt via return e-mail.

5 · Word processing documents -- Because of the way in which the Internet is set up, it is not possible to create a document in WordPerfect for DOS or Windows, or Word for Windows, and to send that document as an Internet electronic mail communication unaltered. Instead, a process known as “encoding” (different from encrypting, mentioned below) must be used to strip away the so-called formatting (headers, bold face type, columns, and the like) that a word processing document will have in ordinary course. The encoded document is transmitted via Internet electronic mail as a so-called “text” or “ASCII” communication, and the recipient must use a “decoding” program to make the stripped formatting reappear. This process is not totally reliable and formatting can be lost or information in a document can be altered inadvertently. An alternative is to send and receive via the same commercial electronic mail system.

Another serious issue to bear in mind is the hidden information that often accompanies word processing files that are transmitted to someone else. Believe it or not, it is sometimes possible to find supposedly deleted text in a word processing file, because the supposed deletions were simply hidden and not removed from the document in its computerized form. To avoid this risk, you can convert the word processing document to plain text or ASCII format.

Choice of method of transmission -- Before you use e-mail or any other method of business communication, the appropriateness of all available methods should be considered. Keep in mind your typing skill, the nature and length of the communication, the recipient’s technology, and the nature of the legal matter (including whether privilege and work product protections are intended to be maintained).
Confidentiality is questionable. -- E-mail can end up almost anywhere on or off the Internet. Sometimes the sending process is flawed: just one misplaced character in the address being used (agoldberg@goulstorry.com instead of agoldberg@goulstorrs.com) can result in the e-mail going to someone many thousands of miles distant from the intended place of receipt. Although sometimes a return message indicating a miscommunication is received by the sender, this is not always true; if the misplaced character address is a real Internet address, the e-mail will be received by the (mis)addressee.

Eventually, many Internet electronic mail systems will use a special encryption program that changes a communication in a way that prevents unauthorized persons from reading the communication and requires a technological “key” to open. These programs are complex and are not generally used by law firms. Until encryption is generally available, e-mail (and indeed, most mail) is not a fully secure method of communication; many users obtain advance permission and a privacy waiver (in written form) from intended recipients to the use of Internet electronic mail, as do some users of cellular phones. Other users simply remove identifying features (names, dates, etc.) from e-mail and replace the same with common words (Dodgers vs. Giants in lieu of Goldberg vs. Smith, for example, in the caption of a litigation proceeding).

6 · The medium affects the message. -- Remember that Internet electronic mail is quite different, in affect and effect, from voice-to-ear and paper communications. This heavy user of e-mail has found that e-mail causes people to behave and react in unexpected ways. Maybe it’s the simplicity; maybe it’s the speed; or maybe it’s the 18 inches between the fast-flickering video monitor and the eyes. Whatever it is, it is; and it can be a challenging and frustrating experience. Use e-mail wisely and remember the now-famous cartoon in The New Yorker magazine of a couple of years ago: two puppies sitting in front of a computer monitor -- one says to the other: “I love the Internet; on the Internet, no one knows I’m a dog.”

As more lawyers and law firms become comfortable with e-mail and economic and competitive pressures push lawyers toward greater independence from secretarial and other support, the issues raised above and others will become significant. Unfortunately, many law firms spend more time and money on the technological side of computerization (software and hardware) than on training people how to use technology properly.

No matter how good a computer system is or how well the engineers and programmers do their jobs, working with a powerful and complex medium requires careful thought. The wise law firms realize that all the money in the world spent on technology is for naught if the people who use the technology don’t know how to use it correctly and safely.

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Last revised: 12/20/97