Verify Your Email Addresses

Misdirected emails are no joke. The addition or deletion of just one character in the address can send confidential or merely embarrassing information moving at the speed of byte. A Boston law firm recently had this lesson glaringly reinforced. I had to share it both for the humor, and for the lesson clearly illustrated. I read about it online in an article by Roger Parloff in CNN He writes:

Job application etiquette: the polite rejection letter

A lawyer I know sent me the following email exchange relating to an interview for employment at a trusts & estates firm in Boston. I verified its authenticity from both ends of the exchange, but have taken pity on the law firm, and will withhold its name and that of its administrator. The exchange demonstrates the importance of examining email addresses closely for unexpected things like middle initials or appended numbers. (For ease of reading, I’ve rearranged the thread so you can read from top to bottom.)

From: A.L.
Date: February 14, 2007
Subject: Law clerk position
To: Samuel F.

Hi Sam,

I am in touch with you regarding your email to M. L. about employment with our firm. We are currently looking for a temporary law clerk.

I’d be happy to meet with you. Please let me know when you’re available.


A. L.
[Law Firm and address omitted]
Boston, MA 02108

From: Samuel F.
Date: Feb 20, 2007 6:25 PM
Subject: Re: Law clerk position
To: A.L.

Dear Ms. L.,

Your message was a pleasant surprise. Regrettably, I must decline. My schedule as a second-grader is quite hectic already. Moreover, I am very busy planning my eighth birthday party next month.

I will of course keep you in mind when I graduate from law school in 2024.

Samuel F.

Yesterday I spoke to A.L., who said she’d meant to write to a different Samuel F. –a recent graduate of American University Law School who had submitted a resume to the firm–but had inadvertently omitted a character from the email address.

Since the Samuel F. who received the email also happens to be the son of a lawyer, I have my suspicions that his father may have lent him some assistance with his reply.

Gee, you think? 🙂 You’ve got to love a lawyer with a wry sense of humor. I’m sure this exchange will be the subject of much laughter at cocktail parties and bar events for years to come. And thanks to the internet, it is already being shared globally.

But the underlying events aren’t really very funny for law firms, so wipe that smile off your face. Imagine that instead of a job interview offer, the email contained sensitive or embarrassing information, or worse, a confidential and potentially dangerous attachment which was not encrypted or passworded. What consequences, aside from the humiliation the Boston firm — certainly not anonymous in their local community — suffered, would accrue? Malpractice? Probably. Economic loss? Probably. Damage to the firm’s reputation? Definitely. This really is no joking matter.

For a few years now I have been privy to confidential email exchanges among a group of teachers in New Hampshire. No matter how many times I “reply to all” to advise that I am not the person they wish to include in their mailing list, and request to be removed, I still continue to occasionally receive emails from one of them who has not made the correction. Troubling that despite my repeated warnings and requests, I still receive emails here and there all this time later.

If you’re thinking this can’t happen at your firm, think again. With the common practice of decentralizing contacts, it’s easy for one person to receive or note a correction, while others are not notified and continue to use an incorrect address. When email addresses are entered “on the fly” by typing them into the address line, mistakes abound. Even use of the “address autocomplete” feature in Outlook can have dire consequences for those whose mouse skills are sloppy — it’s just too easy to accidentally click on the wrong name in the suggested list of names.

One of my fellow practice management advisors in another state suggests turning off the address autocomplete feature as a safety precaution. I disagree. I think that’s like throwing out the baby with the bath water. It’s a tool which is a real time-saver. But as with any tool, one must use it carefully and skillfully.

Personally, I find that the address autocomplete at least eliminates the possibility of totally typing in a wrong address for someone who has previously written to me. If the name does not pop up in the suggested list as I start typing, I know I’ve mistyped. So I find that it is a safety feature to have it ENABLED rather than DISABLED. [Tools / Options / Preferences / Email Options / Advanced Email Options / check box for “Suggest Names While Completing . . .” ]

On the other hand, I must admit that I have on rare occasion sloppily clicked on the wrong name in the suggested list of names. And that leads to the next point — always double check that you have the correct party(s) in the address line(s) before you hit send.

Try to use a centralized contact list at your firm. That way if a correction is made, everyone will use the corrected address. Create a contact for anyone you will probably want to maintain contact with, no matter how infrequently. If you take care in creating the contact accurately, thereafter, you use that contact address, and can’t inadvertently misdirect email. Ok, you’re thinking that if you have four John Smiths in the database, you might pick the incorrect one. But that’s why you have the free text area in your contacts — so that you can enter enough information about the person or company so that you can correctly identify them later.

If I click the “TO…” address button on an email, it takes me into contacts. If I then search on “Smith” and come up with four names, I click on one and click “Properties” which opens a view of the entire contact. I look at the company name, text area, and sometimes (often, actually) I have an actual photo of the contact. With these additional pieces of information I can be sure of the selected contact. And not worry about mistyping.

I also include the company name in the title of the email address. So for the name associated with the email address I don’t let Outlook default to Instead I type John Smith @ ABC Law Firm. That way it is much easier for me to pick the correct name from the address autocomplete list, and to spot mistakes before I hit SEND.


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