GPSolo Magazine - June 2005

The Uses and Misuses of E-Mail
An Electronic Roundtable Discussion Moderated By Jennifer J. Rose

GPSolo gathered eight lawyers for an electronic roundtable discussion of the uses and misuses of e-mail, the joys and agonies it brings to a law practice, and the best advice for surviving the deluge.

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.

Dan Coolidge, patent and general intellectual property attorney in Warner and Keene, New Hampshire. Exotic-wood button manufacturer and wastrel. Number of active e-mail addresses: six. Passive in one listserve. E-mail client software: Outlook, contemplating a switch to Thunderbird. Says his e-practice is “good but fraught with potential disasters. Do as I say, not as I do.”

Bruce Dorner, solo lawyer in Londonderry, New Hampshire. Number of active e-mail addresses: five. E-mail client software: Outlook Express. Always looking for a better way to consolidate but not willing to pay for the high-priced spread. Says, “Frustration with spam led me to use Mailwasher, an add-on anti-spam software package, with good results.”

Vicki Levy Eskin, small firm lawyer in central Florida. Number of active e-mail addresses: five. E-mail client software: Outlook and occasionally an AOL account. Says that e-mail has “expanded my world, opened up a completely different client base, and introduced me to more colleagues and friends than I would ever have thought possible.”

Patricia M. Joyce, solo lawyer representing businesses and individuals in Rhode Island and Massachusetts. Number of active e-mail addresses: seven. E-mail client software: Outlook, past 18 months; previously, Netscape, seven years.

Frank J. Kautz II, general practice attorney in Woburn, Massachusetts. Number of active e-mail addresses: 29. Number of listserves: 23. E-mail client software: Calypso 3.30.

David Leffler, business attorney in three-partner law firm in New York City. Number of active e-mail addresses: about a dozen. E-mail client software: Outlook Express. “I am a business networking fool, constantly going to networking events (I belong to two business network groups). I do enjoy it, and it does bring me business.”

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

How frequently do you check e-mail, or do you run it like music in the background?

Solomon: I’m an e-mail addict: Outlook Express is always running, and I usually click over to it at least five or six times an hour. I have a lot of filters set up to shunt messages to different folders, so I can see right away if the new message is a weekly marketing newsletter that I can look at later or a message from a client.

Kautz: It is like music in the background. My e-mail client software checks about half of my accounts on a minute-by-minute basis; the others every five minutes. Now, this only happens when the computer is on and active, which of course is much of the time.

Coolidge: E-mail runs all day in the background. If I’m on the road, I check once a day. If I’m on vacation, I turn it off.

Leffler: Like music playing in the background. Sometimes I shut down my e-mail client software so it doesn’t distract me.

Joyce: I like the analogy to music in the background. That would probably best describe my scenario. I check it first thing in the a.m., delete all the spam and porn that made it past my filters, and flag items to be addressed later. If I receive a communication for a time-sensitive matter (such as a client attempting to clear up impediments to refinancing business real estate), I tend to respond immediately. Otherwise, I check e-mail randomly between other tasks or while waiting for a callback when I don’t want to start another project.

How has e-mail helped your practice?

Solomon: If I didn’t have e-mail, my practice would look vastly different than it does today—chances are I wouldn’t even have a practice. The ability to exchange documents by e-mail makes 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 in both time and effort. For this reason I adopted e-mail early on and dragged a number of my clients kicking and screaming into the Internet age.

Kautz: Listserves have enabled me to get clients I would never have had otherwise, as well as to make friendships, bat ideas around, and get perspectives from other jurisdictions.

Coolidge: I do all of my client communications through e-mail. I file patents online. I do trademark searches online. I don’t need a library—it’s available online. I could not have my practice without the Internet and e-mail.

Leffler: Communication is much more efficient. I can have a conversation with one person or six people at once without having to schedule a time when everyone is available. Delivery of documents is also easier. Of course, there is a downside to this: You can’t tell your client a task is done and that they’ll receive it in tomorrow’s mail or FedEx, giving you the rest of the day to actually finish it. If you say you have finished a document, you better have, because your client will want it e-mailed right away.

Joyce : E-mail has helped me to promptly provide information or respond to inquiries from clients or other attorneys and business colleagues. The most important aid has been cutting down on telephone tag. With voice mail, many people merely leave a message saying, “Call me.” When those same people use e-mail, they tend to give more details about their inquiry or response. Another asset is the ease of sending documents. At the moment, my WinFaxPro has some bugs, so I’m convincing some reluctant recipients to accept their documents via attachments, particularly PDF (portable document format) files, rather than via fax. Many e-mail users have no clue about the ease and usefulness of these features.

How has e-mail changed in the past decade?

Kautz : It’s gone from something that techies use to something that has become almost indispensable for operating businesses. Everyone from the super-techie to people who know little more about computers than how to turn them on is sending e-mail. E-mail by itself seems to be the reason that many people buy computers, as opposed to its being just one of the programs they use. E-mail allows almost instantaneous communication with people across the globe. It is used in business; it is used privately; it is used to communicate with soldiers on deployment; it is used for almost every reason imaginable. The move from simple ASCII-based text mail to HTML-coded mail has also changed e-mail, not necessarily for the better. HTML e-mail enabled sending messages with pictures, fancy fonts, and other graphic elements. Video mail just never caught on, even though the technology has been around for a while. The real question is where will e-mail go in the next ten years.

Coolidge: E-mail has gone from a luxury to a necessity. My practice runs on it. I work out of a tiny office, with clients around the world, and I can easily communicate with all of them. I am not an e-mail junkie—I can go three hours without checking it. I’ve gotten quite used to having it running while I work, but I can readily ignore it when I want to. The bells-and-whistles stuff is nice, but non-essential HTML messages and the rest do little for me. Sending and receiving file attachments is a godsend, as is high-speed access. Spam is a nuisance, and spam filters necessarily will get smarter. The government will find a way to tax e-mail.

Leffler: The biggest way that e-mail has changed in the past ten years is that it has become universal in the business community. Everyone has it. I remember being laughed at when I added my e-mail address to my law firm stationery in 1993—people didn’t know what it was. I also remember the first time I overheard someone talking about being “e-mailed” about something. It was a new word, a new world, and now it’s as common as making a phone call.

I marvel at the evolution of business cards over the past 100 years. First they had only a person’s name, a company name, a street address, and a city and state. Now a card also has a telephone number, ZIP code, fax number, e-mail address, and sometimes a website address as well. Plus direct-line phone numbers and cell phone numbers. I’m waiting for everyone’s public key for encryption purposes to show up next.

Joyce: When I got my first e-mail from a client, my heart skipped a beat. It was waaay cool. Now it’s often just one more thing demanding my attention, and many clients seem to think that because e-mail travels quickly, a lightning-fast response should follow. On the positive side, since more and more people are using the medium, I often ask potential clients to send me a narrative describing their situation so I can read it later and be in a better position to respond to their questions.

Coolidge: I am spoiled. My clients, for the most part, are also friends. And I have a sense of humor that often gets in the way of, how shall we say, the more traditional practice of law. I just finished a major licensing deal that left me friendly with not only the principals on the other side but also their counsel. The negotiation of significant deals need not always be contentious nor huffy. We got the deal done in record time, all through e-mail, and very pleasantly as well. E-mail can be personal—it can be a vehicle for new communications with people you haven’t yet met in person. You just have to be aware of its inherent ambiguities and deflect unintended consequences. The frequent use of the emoticon helps.

How do you integrate e-mail with case management? If applicable, what is your case management system?

Kautz: This is probably the one point where my office breaks down a bit. My integration is manual. I save my e-mail messages to the same directory where I store all of a case’s files. I calendar items on Amicus Attorney. I have not automated this process; I may or may not in the future.

What’s the best thing about e-mail today?

Solomon: E-mail fills a niche between the insistent clamor of a ringing phone and the time delay inherent in snail mail. Faxes also fit in that niche, but they don’t have some of the other benefits that e-mail does. For example, for most people a fax is still a stand-alone machine using up toner and paper; e-mail is “free”—once you’ve paid your monthly ISP charge, which also covers web access. E-mail also lets you include prior exchanges on the subject instantaneously—no flipping through a file to find previous correspondence.

Kautz: It’s easy to use and almost universal now for people to have an e-mail address.

Eskin: E-mail helps me to keep contemporaneous notes on communication with clients. Before e-mail, I was pretty dismal at documenting files; I kept a lot of information in my head but didn’t always reduce phone conversations to writing. Now, I save all e-mail communications with clients and most interoffice exchanges about case progress. It has vastly improved my office efficiency.

Coolidge: It’s there. It’s ubiquitous. Nearly everyone is online, and those who aren’t are dinosaurs. E-mail enables my practice—it reduced that paper clutter (I can deal with disk clutter).

Leffler: You can answer it at your own convenience—if you aren’t completely overwhelmed with too many e-mails and deadlines.

Solomon: I don’t know if it’s the “best” thing about e-mail, but I love being able to receive faxes by e-mail. I use MaxE-mail’s “lite” plan, which is only $14.95 a year for a very high monthly “message” limit. (You can also receive voice messages at the same number, but I don’t use that feature.) The last thing I wanted as a solo with a home office was the clutter of a fax machine along with all of my other office equipment. For years I received faxes that went directly into a fax program on my computer via my office phone line, but I couldn’t leave the fax program running all the time because it interfered with voice mail. I also needed to use the same line for dial-up Internet access (I’m now a happy convert to DSL, thank goodness). Anyone who wanted to send a fax had to call first and tell me to put my fax on. Now, I can receive faxes 24 hours a day in PDF format. It’s much more professional than my old setup.

What’s the worst thing about e-mail today?

Kautz: Its ease of use—there are far too many fools using e-mail today.

Eskin: It’s pretty addictive and time consuming. A few more problems: the “oh-no” trauma, which occurs a nanosecond after I’ve sent an e-mail prematurely; the inevitable misunderstandings that occur within any verbal or written communication; and how difficult it is to convey all the nuances that face-to-face verbal communication allows—although in many cases, that may also be a blessing.

Coolidge: Spam is awful—really just annoying. Client expectations have to be managed: Sending a message doesn’t guarantee immediate response. It’s just like the early days of faxes.

Leffler: There are too many of the damn things!

rose: The best thing about e-mail for me is not having to speak. Entire issues of GPSolo magazine have been put together by e-mail. I just finished editing a book for the ABA, and everything from soliciting authors to receiving manuscripts and submitting the final draft was done by e-mail. I’ve been a contributing editor to Internet Law Researcher since 1997, and I have spoken to my editor only once—when he hired me. A guy in Panama hired me a year or so ago, and all communication was by e-mail.

Do you find that more and more business is being conducted without ever uttering a word? Is this a good thing?

Dorner: Sometimes it’s better to meet the client on the Internet. I don’t have to clear my desk, I don’t have to wear a tie, and I don’t even have to shave!

Coolidge: Heck—I can work naked and not scare anyone.

Leffler: About ten years ago I represented a client completely by fax. He was in Korea, had invested in several condominiums in NYC, and was selling them one by one. I never spoke to him; I would fax my questions in the afternoon, and in the morning the answers would be waiting in my fax machine. I closed the sales for him into an account, and wired it out, less expenses (including, ahem, my legal fee) to Korea. It’s amazing that I handled that much money for a man I never met and to whom I had never spoken. Today, we would have done this by e-mail.

I deal with some clients mostly by e-mail, although I like to get on the phone every now and then to chat. I feel that by speaking on the phone every so often, I am keeping the relationship solid, though I suppose some people only want you to do the work. I have a client in Chicago with whom I communicate by phone and e-mail (about 50/50). Next week he’ll be in NYC, and we plan to get together for lunch. It’s a close relationship; he relies on me for some business decisions as well as legal work; we want to have the face time, even in this age of e-mails and overnight deliveries.

Joyce: I’ve had clients who contacted me initially by e-mail, and virtually every aspect of their case was conducted in that manner. Not having to speak is one of the most elegant aspects of e-mail.

Eskin: I have a great many clients with whom all or virtually all communications take place by e-mail. In addition to the speed and ability to keep an accurate record of information exchanged, we’ve noticed that it saves the office money on long-distance calls, paper, and postage. We e-mail probate documents to clients; they print, sign, and return originals, all without a single drop of printer ink ever being used by our office. I can also communicate with my office and with clients when I’m on the road without worrying about access to a printer, fax machine, or a FedEx or postal delivery. It’s an efficient and cost-effective means of communication for my business.

Are other forms of communication preferable to e-mail during certain phases of practice? When should the telephone or snail mail be used instead?

Kautz: E-mail is a tool, not the be-all and end-all. Like everything else, it has its place, just like faxes, snail mail, phone calls, and face-to-face meetings. I find phone calls far more effective for negotiations and for coordinating schedules. Snail mail is far more effective in making sure that a person receives the letter (using a certified return receipt, for example). Further, many courts require snail mail delivery. Finally, not every lawyer is an e-mail fanatic; some might not check their e-mail for days. Judges understand how important it is to respond to formal letters and even faxes; they do not always take the same stance with e-mail.

Coolidge: E-mail is inherently impersonal. If you want to establish rapport, you need to speak directly with someone. Once the relationship exists, e-mail can support it, but it’s not a replacement for face/voice time.

Leffler: One great tip is to use a handwritten note on nice stationery for a special thank you or other communication. It really stands out. Phone is good when an e-mail might be interpreted in different ways, because there are far more limitations on the written word than on speech, where inflections count for a lot.

Solomon: I prefer not to do intake with new clients by e-mail; even if the client first contacted me by e-mail, I call to introduce myself. Since I have a nationwide practice, I may never meet some of my clients face to face. Trust is an important element in the practice of law, and I can’t imagine really trusting someone enough to hire that person without at least talking first. Talking on the phone also allows me to have real-time give-and-take with potential clients and allows me to more effectively close the sale because I can address all of the person’s concerns about outsourcing in general, or about hiring me in particular, in one conversation.

What are the big legal issues concerning the use of e-mail?

Solomon: The main issue for lawyers is confidentiality. A number of bar associations, including the ABA (in Formal Op. 99-413) and the New York State Bar Association (in Opinion 709), have concluded that lawyers can communicate confidential information by unencrypted e-mail without violating any ethical rules. New York statute CPLR 4548 explicitly states that, for evidentiary purposes, an otherwise privileged communication does not lose its privileged character solely because it is communicated by electronic means or because “persons necessary for the delivery or facilitation of such electronic communication may have access to the content of the communication.”

Another issue—and there’s actually an ALR annotation on this topic—is whether the statute of frauds can be satisfied by e-mail communications. The statute of frauds generally provides that certain contracts have to be in writing and signed by the party to be charged in order to be enforceable. Almost all of the courts that have addressed the issue have held that an e-mail message containing a typed “signature” is sufficient to take a contract out of the statute of frauds.

Kautz: The issues involve privacy, confidentiality, the fact that e-mail is not perfectly reliable, and the “permanence” of e-mail (once it’s sent, you don’t get it back, and if it’s sent to an archived listserve, it will be there forever).

Leffler: Read the front page of the newspapers and you’ll know. As I read in one recent newspaper report, “Love may not be forever, but e-mail is.”

You really have to know that when you send an e-mail to someone, especially someone in a large company, it will be sitting there in backup tapes and backups of backup tapes for a long, long time. And anyone could see it. So be careful what you put in your e-mails. Be sure not to blow the attorney-client privilege by including your client on a list of addressees that includes others’ e-mail addresses for no necessary reason—especially opposing counsel. I’ve seen it done. And while it may be questionable how much the attorney-client privilege is affected, why mess with it? Send the e-mail to the appropriate parties, then forward it to your client.

What do you find most irritating about e-mail?

rose : E-mail stationery and lawyers who send e-mail in the form of an attached letter really drive me nuts. Those who send e-mail without a subject and who answer with simply a one-liner without quoting the prior e-mail, making me play a guessing game, really irritate me.

Coolidge: People who choose not to use capital letters in their e-mails annoy me. Spam. Getting automatically put onto a mailing list that I have to do something to get off even though I never asked to be on it. Chain e-mails—the kind with a dopey story that you must send on right away to your entire mailing list or dire consequences will follow—why do people forward these? Bad typing. Bad accidents on the Ngambe Road and tons of money looking for a home, and other scams and spams.

Leffler: The one-liner without the previous text drives me nuts, too. My pet peeve is someone who distributes a message to many unaffiliated people, putting them all in the “cc” box so everyone’s e-mail address is exposed, instead of in the “bcc” box, which keeps everyone’s e-mail address private. I’ve seen some horrible examples of this where the sender really should have known better. Also, otherwise intelligent people who unknowingly send hoax virus alerts—and the e-mails claiming, “send this to ten people and you’ll get a million dollars, delete it and you’ll die in a week of a horrible disease!”

Kautz: All of the above, and more. People who don’t check things out before sending them along to everyone on their mailing list. Rumors that once took months or even years to circulate across the country now take weeks to days. Those rumors have a life span that is far in excess of reason. Take the rumor that the post office wants to start charging for e-mail. I first remember seeing a version of this e-mail back in 1993 or 1994. It continues to pop up time and time again. (For the truth behind this rumor, go to’s explanation at Chain letters/e-mails, particularly those that threaten dire harm if you don’t forward them to ten people within the next 15 seconds.

People who don’t check whether the recipient has a high-speed modem or just a dial-up connection before sending a huge file. People who just got e-mail and feel it’s absolutely necessary to forward every joke they receive to everyone on their e-mail list, particularly the jokes that have been around since the early 1990s. People who don’t clear the headers from the e-mails they forward so that you receive 40 lines of e-mail addresses of people you do not and never will know, before getting to the actual e-mail. People who don’t use bcc when forwarding e-mails to a dozen other people.

Viruses. People who don’t use virus checkers or keep them up to date. They never seem to know that they have a virus and proceed to try to infect everyone else in the world. Combine this with all the people doing all the things we’ve already mentioned, and you have the potential to shut down the entire Internet with one really good worm (not to mention causing major problems for friends, associates, and total strangers). People who do not pay attention to the rules of various listserves and push their own political agendas or simply pick a fight. People who beat the spot where a dead horse once lay. People who say things in e-mail that they would never dream of saying to someone face to face. People who do not use proper grammar or punctuation or even bother to turn on the spell-checker.

Solomon: Businesspeople (even, shockingly, salespeople) sending business-related e-mails lacking a signature block with full contact information. People on listserves sending “me too” or “welcome to the list” e-mails that don’t have any value to the list as a whole.

rose: Bad grammar.

Eskin: Those things bother me, too. But I also get irritated when I get e-mails from people using funky names that don’t remind me who they are, particularly if they refer to previous correspondence to me that isn’t included. Why is a client whose name is John, who is nicknamed Jack, using the e-mail name Willie?

How do you keep e-mail from overwhelming you or forcing you to drop everything and answer it immediately?

Coolidge: Look—I can choose not to answer a ringing phone, so I certainly can choose my times for looking at and responding to e-mails. This is a matter of self-discipline. There are plenty of things that could make me frantic if I let them.

Leffler: Shut down my Outlook Express. Get organized (keep client e-mails separate from all other e-mails). Try to control the compulsive need to answer that e-mail from a client right away.

Kautz: The same way that I ignore the phone when I’m with a client or working on a particularly difficult brief. I just shut it down and go to work. The key is discipline, just as in any other area of life.

Which features would you use to build the perfect e-mail client software, and which would you delete? What features in your current program are totally useless? What made you select your current e-mail program, and what would make you switch?

Coolidge: I chose Outlook because it was adequate and universally supported to sync with my PalmPilot. I am looking into the Mozilla e-mail client software mostly out of curiosity (I switched to Firefox for my browser out of frustration with Explorer’s lack of security).

Leffler: I’d add better organization and flexibility in how to access and view e-mails. The totally useless feature on Outlook Express is Help. I admit, inertia made me select my current e-mail program. But a popular program has advantages, not just the drawback of being a leading target for virus makers. For example, desktop search tools typically include Outlook Express in their indexing. So there are benefits.

My use of Outlook Express reflects my tendency to stick with mainstream products no matter how “cool” or otherwise useful other products may be. My philosophy is that mainstream products are less likely to become orphaned by a company’s going out of business or to have support for the product be discontinued because it’s not profitable. However, there are some good arguments for leaving Outlook Express, including serious security concerns and other software that is better designed and offers greater functionality. Which leads to my ultimate conclusion about technology and my law practice: Choosing technology means choosing where you want to compromise. Ultimately, no choice is going to be perfect, so figure out where you are most willing to settle and go that way.

I have about a dozen e-mail addresses, one just for Solosez, one for my eFax account, and one that I make public. All of those come off a single AOL account that gives me seven e-mail addresses to play with. Two more AOL addresses are from my earliest days of e-mail, which for me was about 1990 (yeah, yeah, I know there are those of you who go back to 1979). I use these when a website requires an e-mail address for whatever reason; they get a lot of spam. My personal domain name e-mail addresses get almost no spam, which I cannot explain other than I don’t use them on any websites or listserves, so perhaps that has been enough.

Kautz: I originally went with Calypso back in 1994. I was using Netscape’s e-mail client, but it could handle only one e-mail account at a time. Calypso was one of the first programs to handle multiple e-mail accounts. In particular, you can run multiple versions (mailboxes) of the software to keep business and personal accounts entirely separate if you use multiple addresses. It also allows multiple addresses in the same mailbox. Using that with directories allows me to easily sort messages. Over the years, I began to enjoy Calypso and found it was far easier to use than most other programs. Unfortunately, in 2001 or 2002 the company stopped updating it because it was no longer profitable. Great software engineers, lousy marketers. It does have the advantage of not being a Microsoft product and thus being a bit more resistant to viruses. I’ll eventually be forced to switch when I’m unable to read messages because my software is too old. Sigh.

I find most e-mail features useful. I don’t use some, such as setting priority flags, but there was a time that I did use them. Nothing’s useless. If I were to build the perfect e-mail client, I would start with Calypso and add a feature that prevents showing pictures or other HTML code that is not part of the message. I would add a way to quickly remove “>“ and clean up the spacing, tabbing, and hard returns in forwards or replies.

Joyce: My office uses Outlook (aka LookOut!). I would add a mechanism whereby I could easily copy or move a communication to a client’s case folder, which is on our server and is in a different drive. Perhaps this is available with Amicus or other case management programs. I use Outlook by default. I used Netscape for years and was very happy with it, but the systems person I hired to set up a network insisted that Outlook was more powerful and much more flexible. Even though I had security reservations about viruses, I capitulated because I was also installing XP Professional and Office Professional, which were supposed to play very well together with Outlook and Explorer. I’d switch if I were convinced that Amicus or another case management program would allow easy interaction between e-mail and client and/or other office files.

Any e-mail horror stories you’d like to share?

Coolidge: Some years back when I was chair of an ABA Law Practice Management division, I was trying to get a newbie to attend a meeting being held in Banff, Canada. To get her e-mail address, I looked for an e-mail from her in my saved e-mails, opened it, hit reply to, and invited her to come to the meeting—adding that I had enough in the budget to get her reimbursed. Only thing wrong was that the e-mail I used for her address turned out to be a listserve, and I got about 800 acceptances from the other (merciless) lawyers on the list.

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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