In the Woodpile: Mistakes and the modern lawyer

By Shawn Wood
Seyfarth Shaw

To err is human, but to really foul things up you need a computer.
—Paul Ehrlich

Month after month, my inbox is flooded with solicitations for tech-law seminars. While I’m always struck by the sheer number of these programs and their inspired use of fear as a marketing strategy (”What Every Lawyer Must Know About E-Discovery”), I’m also amazed that these seminars consistently omit one of the most important ”tech” topics of all.

Specifically, I’d like to see a program called: ”How to Avoid Technology Mistakes That Make You Look Really Stupid.”

Professionals clearly need more instruction in this area, and I’m not just talking about minor errors like forgetting to attach a document to an e-mail or those ”all-firm” blasts that always begin with something catchy and sincere like ‘’sorry for the blast e-mail.”

Stories flow through every office about those three terrifying words ”Reply to All” and how a promising career can be sabotaged by sending the wrong e-mail to the wrong 800 people.

In our office, if you click ”Reply to All” in response to an e-mail, the IT folks installed a helpful prompt for the focus-impaired that says: ”DO YOU REALLY WANT TO REPLY TO ALL?” If this doesn’t work, I dropped a note in the suggestion box recommending a second prompt that says: ”HEY IDIOT, IF YOU KEEP SENDING THESE TO EVERYONE, THE FIRM WILL REVOKE YOUR E-MAIL PRIVILEGES.” If they implement my suggestion, I think I win a free taco.

In 2008 alone, there have been at least two incidents of lawyers ending up in the news after inadvertently hitting the ‘’send” button.

In February, The New York Times broke a story about confidential settlement discussions between Eli Lilly and the federal government. Portfolio.com subsequently reported that the drug company’s outside litigation counsel inadvertently sent a confidential e-mail intended for her co-counsel to a NYT reporter, who had a similar name and e-mail address.

This story shot through the blogosere with no shortage of schadenfreude that a mistake had been made by a ”high-priced” partner from a ”fancy” law firm. By the time the reporter clarified that he derived the details of his story from other sources and that the inadvertently sent e-mail consisted of only two sentences (merely stating that the government’s demand was in the ‘’stratosphere”), the damage was done. This story became a parable for the need to exercise greater care when communicating about confidential information.

The second recent e-mail gaffe involved the settlement of a lawsuit an insurer had filed against the Mississippi attorney general. The Associated Press reported that a Skadden, Arps, Slate, Meagher & Flom attorney representing the insurer was copied on an e-mail sent to reporters that contained a press release by the attorney general. The lawyer intended to forward the e-mail to her internal team while commenting that the attorney general should be held in contempt for misrepresenting the terms of a confidential settlement. Instead, she hit ”Reply to All.”

Her comments were sent to a dozen reporters. I suspect this problem could have been avoided by having an auto-prompt that says, ”ARE YOU SURE YOU WANT TO SEND THIS TO A DOZEN REPORTERS?” Remind me to add that to our suggestion box.

Beyond these inadvertent disclosures, the ever-increasing prevalence of blogging creates entirely new avenues for professional blunders.

My personal favorite goof on the blogging front occurred in the context of a medical malpractice trial in Boston last year. Dr. Robert Lindeman, a graduate of Yale University and Columbia University’s College of Physicians and Surgeons, was sued for allegedly failing to diagnose a patient’s diabetes. It turns out defendant Lindeman also maintained an anonymous blog under the screen name ”Flea.” (Ah, yes, sign me up for medical care by the dude who refers to himself as ”Flea.”)

Doc Flea, according to the Boston Globe, was maintaining a real-time blog during his own medical malpractice trial, in which he ridiculed the plaintiff’s case, revealed the defense strategy, and accused members of the jury of dozing. He also wrote about the plaintiff’s attorney Elizabeth Mulvey, who he nicknamed ”Clarissa Lunt,” and remarked about her habit of biting her nails, and reportedly mused: ”Wonder if she’s a pillow biter, too?”

So imagine the surprise of Doc Flea and his lawyer when, at the close of the day during cross-examination, Mulvey asked if Lindeman maintained a blog and whether he was Flea. After Lindeman answered yes to both questions (”D’oh!”), with Mulvey having telegraphed that she was prepared to delve into Flea’s colorful descriptions regarding the case (and everyone in the courtroom), the case promptly settled.

With this non-exclusive list of recent stories involving professional pitfalls, it seems appropriate to add ”avoiding stupidity” to the list of topics at the next round of tech law seminars.

In the meantime, I recommend reserving use of your computer for the really important things, like fantasy baseball, searching for new music on Pitchfork, or watching that Jimmy Kimmel-Ben Affleck video on YouTube.

Or, if nothing else, just avoid ever hitting ”Reply To All.”