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How to Avoid Legal Nightmares in Emails and Instant Messages

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Imagine discussing an employee-related legal concern with your boss, in-house counsel, or outside labor attorney, only to realize that you wrote something in an email or instant message that could devastate your case in litigation. Have you ever heard something like: “Paul, don't worry. As long as you didn’t reference his age in that email or refer to him as a dinosaur or anything similar, we’ll be fine. ... Wait, you didn’t commit that to an email, did you?” (Gulp!) 

Time to ‘fess up. If you did it, own it. But now, of course, it’s too late to undo your mistake. Instead, you’ll have to find that email and prepare a defense around why you may have written it that way, or you’ll fall on your sword and confirm that you were wrong to reference a former employee’s age in the context of a performance review.

Whatever your response, your company will have to dig itself out of a legal hole and overcome a setback that will clearly be exploited by a plaintiff's attorney: “Mr. Falcone, I see that in your email from 11 December, you referenced my client as a dinosaur—someone from the prehistoric days before computers. You appeared to be making a joke about it in your exchange to Patricia Murphy. Did you find it funny at the time? Was your intention to get a laugh at my client’s expense? Maybe you were looking to denigrate and humiliate him in the eyes of your peers. Could that have been the case?”

If only you had known at the time that this particular email—one piece of electronic communication that could be taken out of context months later to demonstrate the alleged animus that you harbored against this individual due to the protected characteristic of his age—could come back to haunt you while you were being deposed in a law office or in front of a jury on a witness stand. Such are the makings of careless mistakes that executives and managers can potentially engage in without thinking of the ramifications of their actions should a case proceed to litigation. 

Here are several key concepts to understand when attempting to avoid online communication nightmares.

Email Comments Will Be Used as Evidence

“First, understand that the ‘e’ in email stands for evidence,” said Jeff Nowak, management-side employment attorney and shareholder at Littler in Chicago, Illinois. “Email has become to civil law what DNA has become to criminal law: a rich source of indisputable evidence that can change case outcomes on a dime.”

Managers typically write hundreds of emails each day, and as a result, email has become an often-casual means of communicating quick thoughts and ideas. The same goes for instant messages and other forms of electronic chatting.

Email has become to civil law what DNA has become to criminal law: a rich source of indisputable evidence that can change case outcomes on a dime.

“And it’s just this casual informality that makes it all so concerning,” Nowak said. Every electronic communication that a manager writes “has the potential of being blown up on a large video screen and placed in front of a jury as evidence of their state of mind at the time they wrote it—a state of mind that may reveal some form of ill intent that they allegedly harbored against a plaintiff/ex-employee based on that individual’s age, race, disability, or other protected status.”

As a result, most defense lawyers will tell you not to commit anything to email that you wouldn’t otherwise post in the employee newsletter. The same goes for instant messaging and text messaging: All forms of electronic communication are easily obtained from forensic IT consultants who are trained to scour systems for written communications about a particular topic or person. And all it takes is one or several off-color remarks or exchanges about the individual’s background, age, or other protected characteristic to damage or significantly weaken your legal defense strategy. Of course, the comment may be taken totally out of context, but all’s fair in love and war (and in the world of employment litigation).

Never Attempt to Destroy Electronic Evidence

Simply deleting a problematic email may be a mistake for several reasons. First, deleting electronic communication may be ineffective because it often can be recovered after it’s deleted. For example, if a manager were to delete an email, empty the trash folder, and somehow reach into the bowels of the hard drive to attempt to delete the emptied trash folder contents, she still may not be successful in eradicating the message from the system or from the discerning eyes of a forensic IT specialist. 

“Even worse, deliberately or even accidentally destroying evidence relevant to a legal dispute may lead to claims of spoliation of evidence,” said Christopher Olmsted, managing shareholder at Ogletree Deakins in San Diego, California. “If such a claim is successful, it can lead to significant negative consequences in litigation that may be far more harmful for the company than any problems created by the deleted information in the first place.”

Codifying the Damage Is Dangerous

Likewise, be aware of “codifying the damage” in follow-up communication. “For example,” Nowak said, “‘sexual harassment’ is generally considered a legal conclusion. If you write that ‘Connor harassed Emma’ in your documentation, it could likely be exploited by a plaintiff’s attorney to demonstrate that the company recognized that the harassment indeed occurred.”

Rather than making such a firm statement, write something more “specifically vague,” such as, “Connor’s actions appear to violate our company policy on creating and sustaining a friendly and inclusive work environment,” or “Connor’s actions suggest that he didn’t take Emma's prior warnings to keep a safe distance from her seriously.” Always buy yourself the discretion to argue that what you wrote did not codify any damage done to a member of the staff.

Descriptive Words Are Not Your Friend

As a rule of thumb, avoid extraneous description (e.g., words ending in -ly) in your formal business writing. “Sometimes, managers unnecessarily employ words like purposefully, willfully, intentionally, and deliberately to their messages or progressive disciplinary documentation to amplify an obvious point or as a substitute for a detailed factual statement,” Olmsted said. “A precise description of what someone did or said often renders words like ‘intentionally’ superfluous.”

If you stick with concrete facts rather than characterizations, you are less susceptible to accusations of bias or evil motive by an aggressive plaintiff’s attorney during cross-examination. “Mr. Falcone, how did you know my client’s state of mind at that time? How were you so sure that he did what he did deliberately and purposely, as you allege in the disciplinary warning that you issued him?” Those words are considered state-of-mind assumptions, and a plaintiff’s attorney would likely use them to engage in undermining your credibility at the time you disciplined the plaintiff, tying your assumptions about that individual’s state of mind to the person's age, race, gender, or other protected category.

If you stick with concrete facts rather than characterizations, you are less susceptible to accusations of bias or evil motive by an aggressive plaintiff’s attorney during cross-examination.

Employ the Attorney-Client Privilege Properly

Finally, as a general rule, understand how to use the attorney-client privilege effectively. There are specific guidelines that govern how the privilege works that go beyond the scope of this article, but generally speaking:

  • When you address the email to your attorney, mark it “Attorney-Client Privileged” in the subject line, and open the email with “Privileged & Confidential: Attorney-Client Privileged Communication.”
  • Address the email only to your attorney: You can’t claim attorney-client privilege if you’re writing to a non-attorney. If you must copy your boss, make sure that individual has a specific need to know. But if you copy 15 people, a judge will likely conclude that the privilege is not legitimate and make the document part of the public record.
  • At the end of the email, ask your attorney for legal analysis and recommendation.

While the privilege isn’t guaranteed, following these rules will create the greatest chance of sustaining the privilege and blocking that document from becoming part of the public record that jurors may see.

As a practical guideline, any time you’re thinking of marking a document “attorney-client privileged,” call your attorney and discuss the matter first. An ounce of prevention may be worth a pound of cure in such instances.

As casual and familiar as email and instant messaging have become, they are prime hunting grounds for plaintiffs’ attorneys these days. Forewarned is forearmed. These documentation tips will help you steer clear of the snare that potentially awaits in the litigation arena.

Paul Falcone ( is a frequent contributor to SHRM Online and has served in a range of senior HR roles at such companies as Paramount Pictures, Nickelodeon, Time Warner, and City of Hope Medical Center. He's a member of the SHRM Speakers Bureau, a corporate leadership trainer, a certified executive coach and the author of the five-book Paul Falcone Workplace Leadership Series (HarperCollins Leadership and Amacom)His other bestsellers include 101 Tough Conversations to Have with Employees, 101 Sample Write-Ups for Documenting Employee Performance Problems, 96 Great Interview Questions to Ask Before You Hire, and 2600 Phrases for Effective Performance Reviews.

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