GPSolo Magazine - January/February 2006

E-Mail in the Law Office
An electronic roundtable discussion moderated by jennifer j. rose

In the June 2005 issue of GPSolo, we discussed “The Uses and Misuses of E-Mail.” What works well for sending casual e-mail to friends and family doesn’t necessarily play well in the law office. We’ve grown to expect immediate answers to electronic communication, and so too do our clients. With a flick of the wrist and a click of the mouse, lawyers can streamline their practice—as well as risk malpractice and ethical problems. What’s the answer?

GPSolo gathered seven lawyers for an electronic roundtable discussion of the positive aspects and the pratfalls of e-mail in the law office.

The participants

jennifer j. rose, editor-in-chief, GPSolo. Known as “Creature of the Ether.” Number of active e-mail addresses: 13. E-mail client software: Eudora 6.2 and Thunderbird.

Sandon L. Cohen, associate in the firm of Cohan & West in Baltimore, Maryland, concentrating in the areas of business transactions and business planning for small to medium-sized business and also performing a variety of other work for clients and their families. Number of active e-mail addresses: one. E-mail client software: Outlook.

Andrew C. Simpson, solo lawyer practicing insurance defense on St. Croix, U.S. Virgin Islands. Number of active e-mail addresses: six. E-mail client software: Eudora 6.1 but migrating to Time- Matters’ e-mail program for business e-mail. MailWasher Pro to block spam. Number of listserves: four.

Lisa Solomon, sole practitioner in Ardsley, New York, doing legal research and writing for other lawyers on an outsourcing basis. Number of active e-mail addresses: three, including one just for Solosez. E-mail client software: Outlook Express. Number of listserves: two.

Ted Waggoner, small firm attorney in the small town of Rochester, Indiana, concentrating on transactional matters, estate planning and probate, business matters, and related litigation. Number of active e-mail addresses: three. E-mail client software: Outlook Express and Gmail. Number of listserves: ten at the office, two at home. Installing Time-Matters now, training starts next week.

Bob Walker, sole practitioner in Herndon, Virginia, concentrating on estate planning, civil litigation, creditor representation, and creditor-side bankruptcy. Number of active e-mail addresses: three. E-mail client software: Time-Matters 6 (soon to be 7) and Outlook on a laptop.

Robin Page West, partner in the firm of Cohan & West, specializing in qui tam and whistleblower litigation. Editor-in-chief of SOLO newsletter, author of Advising the Qui Tam Whistleblower, and co-author with Daniel Small of Letters for Litigators: Essential Communications for Opposing Counsel, Witnesses, Clients, and Others. Number of active e-mail addresses: four. E-mail client software: Outlook.

How can you commit malpractice with e-mail?

Cohen: I thought I’d rephrase the issue, as presumably no one wants to learn how to commit malpractice.

E-mails should be treated like any other documents a lawyer prepares in a professional capacity. Each e-mail should be fully thought out, revised, and proofread before it is sent. If it contains a legal opinion, the lawyer should ask the same questions, perform the same amount of research, and give the matter the same amount of thought as in preparing an opinion letter or memorandum. Too often, e-mail has an “off the cuff” or stream-of-consciousness quality to it.

Clients often expect quick answers to their questions, not realizing that fast can mean sloppy and that no lawyer can know all of the law. If you can’t persuade clients to wait until you have had time to give the matter sufficient research and consideration, you should add a disclaimer to the effect that your answer is preliminary and should not be relied upon unless you are given an opportunity to take the necessary time. If you don’t have a good idea as to what the answer is, you shouldn’t even give clients a preliminary answer.

Senders tend to assume both that the recipient’s computer received the message and that the recipient is in his or her office to review it. Just last week I sent a client with whom I have previously communicated by e-mail a message with a draft letter attached for his review. The client didn’t get this message, even though I had sent it to the correct address and even though I didn’t get an “undeliverable mail” report. If you have something for a client that requires immediate attention, you should use the telephone to convey the information or at least to advise the client to expect your e-mail.

If you use contracts or other work product from past transactions to prepare new documents for other clients or have revised a document based upon a client’s comments, there are potential problems in e-mailing these documents in their word processed form to other clients or third parties, because the previous versions of the document can be recovered, along with other confidential information, as embedded “metadata” in the file. I’ve also read that this problem can be eliminated by putting the document in PDF or limited in the case of a Microsoft Word document by putting it in Rich Text format. Both of these solutions reduce the usability of the document to the recipient and create a plethora of versions of the same document on the preparer’s computer system. The software companies should come up with a better solution. In the meantime, we lawyers remain obligated to protect the confidential information of our clients in the face of increasing demands to e-mail draft documents instead of sending paper versions.

Simpson: I completely agree about using another method to notify a client if you have sent an e-mail that needs the client’s attention. I partially agree with the comments about the quality of the work product leaving a law office in an e-mail. Of course, in the ideal situation, you will proofread your e-mails before sending them out, but that is not always necessary or desirable. Clients like e-mail because of its informality, and their expectations are lower for an e-mail. And clients definitely want quick responses on occasion. The practice of law is a service industry, so we must be prepared to give clients the service they want.

Obviously, if you are responding to an insurer’s request for an insurance coverage opinion, you are going to want to review the issue, perform an appropriate analysis, and respond with the benefit of not being rushed. However, if a client e-mails me and asks, “What’s the statute of limitations for a personal injury tort” and I instantly respond “Two years,” I’ve given the client good, prompt service and there is no need to linger over a question that is black letter law. Clients have told me that they like dealing with me because they know they will get a prompt response to an e-mail. The trick is to know when to be quick and when to put on the brakes. Since we are talking about avoiding malpractice, obviously the more you can wait and cogitate, the better.

For metadata removal, the leading product is Metadata Assistant from Payne Consulting ( Do keep in mind that all electronic data has metadata. For example, Sandon suggests printing a Word document to PDF, and this will remove all of the metadata internal to the Word document; but a PDF document has its own metadata associated with it. Relatively benign stuff, but still information that you might not want revealed. For example, suppose you have drafted a contract for a client and the client is going to present it to another party to the contract. You print it to PDF and e-mail it to the client, who then e-mails it to the other party. That party may be able to view the PDF metadata and determine that you drafted the contract. Maybe the client doesn’t want the other party to know that the contract was drafted with a lawyer’s input.

Cohen: I also agree about providing quick and direct answers to questions that can be answered in that manner. Unfortunately, clients rarely ask such questions. A personal injury client wouldn’t likely know what a statute of limitations is but would give the lawyer a partial statement of facts and ask about the possibility of a lawsuit. (For example, “I slipped and fell a while back on a wet floor in the grocery store, and I was just diagnosed with back problems that my doctor thinks resulted from a fall. Can I sue the store owner?”) The lawyer would need to ask a variety of questions to advise the client, one of which would be what “a while back” means, and might still have to conduct research as to the limitations issue if the forum state’s law provides that the period of limitations begins to run from the date the claimant knew or should have known of the claim. A meeting or at least a telephone conversation is usually needed to develop the relevant facts.

Walker : I do not communicate with clients via e-mail unless I know them.

A few years ago I purchased Payne’s Metadata Assistant. But I do not often send documents to clients in a form that is easy for them to manipulate/change (i.e., I send mainly in PDFs). I do, however, frequently trade documents with other attorneys, although that does require a certain level of trust, of course. But isn’t that (trust) true regardless? There is a real danger of sending an e-mail to the wrong person—not only picking the wrong “contact” but also being careful who replies are going to. It seems to me that it is easier to send e-mail to the wrong person than to send a fax to the wrong person. Caution is definitely needed. I also think we have to be very careful about cc’s for, among other reasons, the unintended or improper revelation of a client’s e-mail address.

Solomon: I’d like to respond to the observation that senders assume both that the recipient’s computer received the message and that the recipient is in his or her office to review it. I have been on both ends of this problem. I exchange documents with my clients almost exclusively by e-mail. A few times, I sent drafts of litigation-related documents to clients and assumed that they received the documents because I didn’t get an “undeliverable” message, only to learn that they never received the documents. Now, when I attach time-sensitive documents to e-mail, I either set Outlook Express to request a read receipt or ask the recipient to confirm receipt by sending me a reply e-mail. These techniques are analogous to using certified mail (return receipt requested) or receiving a confirmation slip from your fax machine.

On the other side of the coin, I have had clients send me e-mails of an urgent nature that were not marked as high priority. I advise my clients that, if something is urgent, they can e-mail me about it but they should also call.

Waggoner: What generally causes malpractice claims? Poor communication with clients is always at the top of any list. E-mail is a good method of avoiding communication problems, if that is how the client wants to communicate. So, first obtain the e-mail address, and then determine if the client wants to get e-mails about legal matters.

Remember that e-mails are not perceived as “secure” communications. They may have the same problems as postal mail for security, but clients (and lawyers) feel e-mail is less safe. A letter left on the table is no more secure than an e-mail in the computer, but we feel less secure about the e-mail, as it is newer technology.

Ultimately, we just have to use lawyerly judgment in choosing methods of communication. Do not let concerns about e-mail security cause you to fail to adequately communicate with your client. That failure to communicate is more likely to cause a malpractice claim than an errant e-mail.

What are the ethical traps in using e-mail?

Waggoner: Ethical traps using e-mail are different from ethical traps with other forms of communication, mostly as a result of the speed of the message. Because the message does not sit on a desk until the end of the day, and usually does not go through the hands of a staff member, the lawyer may say something more impertinent than intended, or something less clear than expected.

Clicking on the buttons for “cc:” or “bcc:” or “send” takes only a moment—much quicker than the time it takes for a lawyer to check a written document after signature and place the letter in an envelope. According to reports I’ve read, misdirected e-mail messages occur more frequently than mis-sent envelopes.

West: E-mail creates a heightened expectation of speedy communication that conflicts with the need to document the file, and be thorough and accurate. I mentioned this problem in Letters for Litigators (which I co-authored with Daniel Small) and the companion article that appeared in Litigation magazine (volume 31, number 3, Spring 2005):

“It would be so nice to be able to neatly confirm everything in writing with opposing counsel and apprise the client of your two phone conversations and four e-mails this morning. But there simply isn’t time before you leave for court this afternoon. Do you keep the information in your head and try to remember to do a letter later? Do you leave the client a quick voice-mail but have no written documentation of the events in your own records? Do you keep up a constant stream of dictation into a portable digital dictation device and days later find your secretary typing obsolete or superseded letters? Or do you reluctantly cc and forward all e-mails to the client in real time, but wonder whether the casual tone and the pleasantries you are exchanging with adverse counsel might seem a tad glib?

“For example, you want your client to know you are diligently following up with the lawyer on the other side to produce documents. You and opposing counsel have known each other forever, and you banter on e-mail much like the text messages your kids send each other on their cell phones. So you send him this e-mail as your train pulls into O’Hare: stan—stunt with the subp will backfire & u know it. dx way overdue. how much longer? golf sat am?

“Should your client actually see this e-mail? Or can you put him on hold indefinitely until you have enough time to draft a proper status report on proper letterhead? Perhaps you should put Stan on hold, too, until you can generate a conventional follow-up letter with completely spelled-out words. When we go back and read this e-mail 45 days from now, will we cringe at the overly familiar tone? Will we—much less our clients or the court—even be able to understand what we were talking about?”

Cohen: My opinions about this topic largely overlap with those about avoiding potential malpractice. Many risks of using e-mail that could lead to malpractice claims could also constitute violations of the Rules of Professional Conduct. See, for example, Rules 1.1 (Competence) and 1.6 (Confidentiality of Information).

No one—I hope—wants to solicit business from anyone who is not already a client by means of spam, which would be subject to whatever versions of Rules 7.1, 7.2, and 7.3 are in effect in each of the jurisdictions to which such communications are directed, as well as to any other applicable laws. Even if this could be done legally, I would consider it unethical in the broader sense because of the waste of time it would impose upon the recipients.

In sum, a lawyer shouldn’t do anything with e-mail that he or she wouldn’t do with other forms of communication.

Do you have an e-mail policy in your workplace to prohibit private e-mails or instant messages?

rose: When I had staff, my problem was staff who used the office phone and my time for personal telephone calls. Today that problem is harder to catch and carries the potential for more damage and downtime.

Walker : This is one of the things I like about solo practice and do not miss from being in a firm.

Waggoner: Our policy states: “The firm has established Internet access throughout the office through the office network. It is primarily for office use and is subject to being monitored for abuse of time or subject matter.” We have few problems, but occasionally we have to have a conversation about phone use, mostly incoming calls from family and friends. In a small town we often confuse the business caller as a personal caller. Our staff knows the bank employee or deputy clerk well enough to ask about family or pets. Walking around and overhearing them we sometimes question these conversations, only to find they were business calls. We have had to talk about intra-office e-mail more than general e-mail. Bad attitudes can quickly build if a staffer starts complaining about other staff on the intra-office e-mail.

Simpson: I haven’t put my policy in writing. But my staff of four knows the policy: They have an e-mail address using my office domain name that is for business purposes only. They are not to send personal e-mail from the office domain name. They are allowed to log on to their own personal e-mail accounts and send personal e-mails from them, as long as they don’t abuse the privilege. Instant messaging (IM) is absolutely forbidden, because it creates holes in firewalls.

I don’t see e-mail as the area that is likely to be abused as much as web surfing or personal phone calls. With my hardware firewall, I can block a lot of surfing activity if necessary. It has never gotten to that point.

How has e-mail changed your practice?

Simpson: My practice depends upon connectivity, especially e-mail. Between my Blackberry, the DSL Wi-Fi cloud at my home, and DSL at the office, I am virtually always connected. I can’t wait until I can access e-mail when flying. I once sent an e-mail to my office from the top of a mountain in Washington state; and lest you think connectivity ruins vacations, I remotely restored my crashed network drive from a backup tape while vacationing in Bermuda—the two hours it took saved me from having to fly home early from vacation.

Solomon: Without e-mail, chances are I wouldn’t have a practice; if I did, it would look vastly different than it does today. The ability to exchange documents by e-mail makes my work—outsourcing legal research and writing—a practical solution for the lawyers who use my services. Other ways of getting my work product to my clients, such as faxing drafts back and forth or putting a file on a disk and mailing it, are much less efficient, both in terms of time and effort. For this reason, I was an “early adopter” of e-mail and dragged a number of my clients kicking and screaming into the Internet age.

Cohen: I have regularly used e-mail for the past two years but don’t care for it. Owing to a mild neurological problem, I’ve never been able to achieve any speed as a typist. I have been accustomed to dictating documents into a mini-cassette recorder, having them typed by persons skilled in that craft (even though few of them exist anymore), making revisions in red ink, and having “real-time” communications in person or over the telephone.

I don’t like e-mail and never will. For me its effect has been to create more interruptions by clients and others who want immediate, written responses to their inquiries, as well as to create the security and other issues recognized above. Two years ago I finally had to get a computer in my office to receive and send e-mail, just to fulfill client expectations. Although I can get some types of work out more quickly than I used to, my total productivity during the workday has declined owing to e-mail and other computer-related issues. I’m getting fewer billable hours in a workday that is just as long.

People can exchange and develop ideas much more quickly by speaking in person or over the telephone. E-mail is an updated version of the nineteenth-century telegraph.

Are disclaimers worthwhile?

rose: When fax machines were new, everyone was in an uproar over disclaimers in the event the fax was sent the wrong direction. Somehow that never seemed to be a concern back in the paper-and-envelope days, when a letter could just as easily be slipped into an envelope addressed to the wrong addressee and delivered by a uniformed agent of the federal government. Are disclaimers on e-mail worth the paper they’re written on? Some of the disclaimers I see occupy more space than the message itself.

Walker : I do not waste the time and toner on them. I don’t see that they are worth much. I see them a lot, though. The various bar rules regarding discovery inadvertently sent would seem to me to provide sufficient protection. How are you going to enforce “I sent you this but you can’t read it”? I doubt that such language on a fax cover would protect us from a client suing or complaining because we sent it to the wrong person and the client thereby suffered harm.

I also wonder whether disclaimershave become so commonplace as to be completely ignored as clutter. When’s the last time anyone read the disclosure on the parking garage stub?

Waggoner: I don’t use a disclaimer on e-mail, although I haven’t taken it off my fax cover sheet. Reading some, they seem like a public relations effort. “See how careful I am, client?” I try not to perform empty PR stunts.

Solomon: I also do not use a disclaimer on e-mail. I just don’t think disclaimers are meaningful in the e-mail context because, even if the disclaimer is placed before the text of the e-mail—which I have never seen—it’s still going to be right there on the same screen (or printout) as the protected message. In other words, the message is going to be read. The question is, what is the recipient going to do with the information? In my mind, the big practical danger is generally not the risk of mistakenly sending confidential information to someone who is completely unconnected to the matter; rather, it’s the risk of sending the information to an opposing party in thematter. That’s because someone not connected with the matter generally will not have any interest in the information or desire to use it to your client’s disadvantage. An opposing party, on the other hand, will have an interest in the information and may be willing and able to use it to your client’s disadvantage. However, once the opposing party (and here I’m also including the opposing counsel) reads the e-mail, it’s too late: you can’t unring a bell. A better solution—again, from the standpoint of practicality—may be to turn off the autocomplete feature in your e-mail program, or to simply make it a practice to double-check who the addressees are before you hit “send.”

Cohen: I agree with everyone about the disclaimer issue. I do note, however, that lawyers who give advice on federal tax issues may be required to give a disclaimer in accordance with IRS Circular 230 when providing such advice. I haven’t lately provided an opinion in this area and haven’t had occasion to review the circular but have noticed the disclaimer on e-mails from a number of law firms. It would be advisable to review this circular before providing advice in this area in any form.

Walker : Yes, I have noticed the Circular 230 notices as well. It seems to me that people have made them part of their signatures. They appear each and every time regardless of whether there is any sort of tax advice given or possible. For example, some have been posted to listserves where the only thing said was something like, “know any good restaurants in Cleveland?” I wonder whether this is some passive-aggressive response to the IRS requirement.

Simpson: I think disclaimers are an utter waste of time for all of the reasons above. If you have to rely upon them, the damage has already been done. All that aside, I try to use them on business e-mail for only one reason: My professional liability carrier recommends that I use them. I figure that if I erroneously send an e-mail, my carrier is going to be on the hook. And if the one that is going to be on the hook wants me to use it, I will.

What are the pitfalls of using e-mail?

Waggoner: I ask clients for e-mail addresses on our intake form, but I have a second inquiry for “where should we contact you?” which came out of some old divorce cases of intercepted mail. If the client’s e-mail is a family address, I do not use that for most things—maybe only for a quick “call us” message—and I would not forward anything substantive without the client’s specific request. We don’t send employment-related matters to a work address.

Simpson: Don’t use e-mail when having an affair. ;) Don’t use e-mail when angry. And don’t use e-mail on those occasions when you think it would be wiser to pick up the phone to advise the client without committing your comments to writing. By saying this, I am not suggesting that the phone conversation is going to involve anything illegal or unethical; but there are times when what you write could come back to haunt either you or your client.

I’m acutely aware of this when advising an insurance client on an insurance coverage issue. My advice easily could be discovered in subsequent coverage litigation in which the insurer asserts reliance on the advice of counsel as a basis for avoiding a bad-faith claim. Let’s suppose part of my advice to the client involves a description of the judges who are likely to rule on the coverage issues if a coverage case is brought; maybe I even suggest a declaratory judgment action so that we can choose our forum and have a greater likelihood of drawing a particular judge who I believe is more inclined to uphold our position. I certainly do not want that type of analysis disclosed in subsequent litigation! And it’s easy to see how the insured’s lawyer might try to twist practical legal advice about how to obtain a favorable ruling into some sort of evil motive on the part of the insurer. These types of discussion do not belong in writing—e-mail or otherwise.


jennifer j. rose, editor-in-chief of GPSolo, is a lawyer and writer living in Morelia, Michoacán, Mexico. She can be reached at


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