Recent tech mistakes in law firms—and learning from them

office errors

While modern technology has certainly made life easier for legal professionals, it has also created a whole host of problems. Emails, instant messaging, social media, and web-based time-trackers are undeniably convenient. Each, however, carries a risk for costly tech mistakes in law firms.

These risks undoubtedly exist in any office environment, but law offices are particularly vulnerable. Lawyers owe their clients a duty of confidentiality. Yet, one misspelled email address can send scores of client information careening across the world-wide-web. An active time-tracker left on overnight can result in grievous overbilling of clients. The examples are endless.

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For some reason, several of these technological snafus have made the news recently. What can be learned from those famous examples? How can we avoid similar mistakes?

The disappearing emails

Not long ago, a Florida firm learned a very difficult lesson about cutting costs with respect to technology. Odom & Barlow’s IT consultant had warned the firm about their spam email configuration. It was set up to automatically (and permanently) delete any message the email server recognized as spam. This was cheaper than paying for third-party spam filtering or installing a backup system that would save everything that came into the firm’s email addresses.

The cost-savings became irrelevant, however, when the server determined that a court order assessing attorneys’ fees was spam. The order was thus auto-deleted and never seen by attorneys on the case. As a result, the firm missed the deadline for appealing the order. The First District Court of Appeal in Florida later ruled that even though the attorneys never actually received the order, their failure to file a timely appeal did not constitute excusable neglect. The appeal was potentially worth $1 million to the firm.

At the very least, be sure to turn off auto-deletion of spam in your firm’s email, and carefully monitor anything filtered by the server. Consider also how an additional filter or backup system could be worth it in the long run.

Authenticating identity

In another recent case, the personal lawyer for Jared Kushner responded to a series of emails he mistakenly believed came from the young White House advisor. They did not. They came from a prankster who was imitating Kushner using the email address [email protected]. The entire, embarrassing exchange ended up in the news and revealed insights into how Kushner and his attorney communicate.

Email addresses can be very tricky. One important practice is to verify each client’s private, secure email address at the outset of the engagement.

Afterwards, pay attention to the actual addresses client emails are received from. Kushner’s lawyer, for example, could have saved himself and his client significant embarrassment if he had taken the three-second step of looking at “Kushner’s” email address.

Redaction omission

Even when documents were redacted using nothing but a Sharpie, there was still the possibility for a keen eye to tilt the page and surmise the details. Now that much of redaction is done using PDF editing software, the risks are just as big, or bigger. Electronic documents hold on to data in more than just the window you see. Metadata, the behind the scenes information, can also give away important details.

The Department of Justice learned this lesson the hard way when a filed motion containing sensitive material turned out to be only partially redacted. It wasn’t until a reporter mentioned the mistake that the document was retrieved and resubmitted, but the information had already been available to the public for half a day by that time.

Try the old trick of copying and pasting the text to see if your redacting was successful. If you can easily read the redacted text in a new file, that’s your first clue that something is amiss. Learn how to correctly redact your legal documents and more about removing metadata from your files before you submit.

Automation in email

Representatives of the firm Wilmer, Cutler, Pickering, Hale, and Dorr apologized last year after a copy of privileged documents ended up in the wrong inbox. Files that “detailed a history of whistleblower claims at PepsiCo” were inadvertently sent to the inbox of a Wall Street Journal reporter. Suffice it to say that, soon, nothing about those documents were privileged.

You think it can never happen to you, but stories like this are enough to make anyone shudder and quadruple check that recipient list. One way for legal professionals to prevent this is to set up their email programs so they do not auto-populate addresses after typing the first few letters. The convenience is not likely to be worth the possible consequences.

Turns out it’s not the first time something like that has happened. One reporter shared that he had once received the billing records for every single client in the firm. Talk about cringe-worthy.

The importance of training

These days, technology has become so ubiquitous with modern practice that employers often presume employees know everything they need to know about the technological tools in the office. That is not a safe presumption.

The obvious remedy for that is to train the entire firm early and often. Many legal software providers will happily visit law firms to train on features and time-saving tricks (many of them will also provide lunch). If your firm is going to invest in the technology, it might as well invest in the employees’ ability to use it efficiently.

As the majority of courts in the U.S. now require that filings and other communications be handled electronically, it is more imperative than ever that law firms take appropriate measures to ensure the security and sanctity of all electronic information. It only takes one mistake like the examples above to make you wish you’d acted sooner.


Have any good stories of legal tech gone wrong—or almost? Share your experiences in the comments.

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