To Send, or Not to Send – That Is The Question

By Ronald Rossi

August 22, 2018

Ron RossiFebruary 1st, 2018 marked my 49th year of practicing law. Having now handled hundreds of jury and non-jury trials, as well as numerous binding arbitrations, I am often asked "what’s changed the most?" since the early ‘70s.

That’s an easy answer. When I started, there were no computers, no fax machines, and no cell phones. The cutting-edge technology back then was the IBM Selectric typewriter. Correspondence had to be dictated or written, typed, reviewed, and then sent out. There was always time to reflect on any written material sent.

I find that the most significant change in my real estate litigation practice has been the advent of email. Most real estate cases involve a substantial number of documents, but now they also involve thousands of emails. I was trial counsel in a development case recently that generated over 400,000 emails. Cases with over 100,000 emails are now commonplace.

It’s amazing what people will say to one another in an email. For some reason, there is a perception that you are "off the record," whereas the truth is that emails are discoverable in litigation. Folks often try to hide or eliminate them, but they don’t get away with it.

I created the following guidelines that I advise my clients to follow when utilizing email.

  1. Send an email, or not? There is a famous saying attributed to no less than the Massachusetts politician Martin Lomasney. He stated with great foresight, "Never write if you can speak; never speak if you can nod; never nod if you can wink." Whether it be internal office communications or communications with third parties, people tend to want to say what they have to say quickly and shoot off an email instead of having a phone conversation or an in-person meeting. The trend of instant gratification is evident in this desire for instant communication. I've heard it described as the "fire and forget it" method. Many attorneys I deal with nowadays won't interact in a phone conversation but instead insist on using email. But if the subject matter is sensitive, and especially if it involves potential litigation, pick up the phone or meet in person and follow the advice of Lomasney.
  2. A good rule to follow: "Think, write; think, send." If you want to communicate something via email or text messaging, review your message carefully before hitting the "Send" button. Some folks, wisely, wait 24 hours before sending a message they've drafted. Always keep in mind that if you are in any type of business (and particularly real estate) where litigation could be involved, some judge, jury, or arbitrator is going to see whatever you sent or received via email in a lawsuit. If there's a damaging email, they'll project it, enlarged, onscreen or create a poster-sized exhibit of it, which can be devastating evidence against you.

In one of my firm's recent cases, the defendant claimed an oral agreement was reached with our client and he was thus justified in relying on that alleged agreement; however, that same defendant had sent an email to one of the brokers that said "nothing matters in real estate until it is in writing." I think you can imagine the effect that exhibit had on the judge and jury - and on the plaintiff's case. I have seen cases in which brokers and lawyers have made racial slurs against the person's client, made exaggerated claims, or used vicious and/or vulgar language that they apparently blithely assumed would never see the light of day. Remember, email, while perhaps seeming ephemeral, is actually as permanent, or more so, than any other form of written communication. A hard-copy letter can be lost, whereas emails can almost never be deleted or hidden. You may try and get rid of your emails, but every email has a recipient(s), every recipient can forward or save or back up your emails, and then there are all the multiple locations and platforms where emails reside and can be retrieved and restored by the tech folks (including computer forensic experts employed by attorneys in discovery and at trial).

3. When you do write an email, avoid hyperbole and resist assigning blame or finding fault. Try to make each message accurate, succinct, and dispassionate - remember that sometimes the fewer words, the better. Be careful to avoid using language in emails that can be interpreted in more than one way.

4. Sarcasm can be an effective writing tool, but it does not belong in an email that may be used against the author in litigation. Remember, all an email or text message provides is text - what is actually written. The facial expressions, body language, and/or tone that accompany and often color spoken expression play no role in electronic communications.

6. Emojis are increasingly popular, but they, too, can be misunderstood. Imagine you're on the witness stand and the attorney presents a damaging email to you in cross-examination. Your explanation of "well, I was just trying to be funny" will not go over well with the judge or jury. 6. If you want to sum up or go over the topics and decisions in a strategy situation between partners or other persons where the email would not be a privileged communication (i.e., not between you as a client and your attorney), don't put that in writing. Comments like "don't tell the other side this," "we need to keep this confidential," or "let's try this little game and see if they fall for it" can ruin a case.

7. People often forget to review the attachments they send with an email. An email may be perfectly fine, but certain attachments can be catastrophic in a lawsuit.

8. If you're emailing your attorney and/or your attorney's staff, always begin the email with the wording "Attorney-Client Communication, Privileged And Confidential - Do Not Disclose" in very visible type.

9. As I mentioned briefly before, never assume you can hide or permanently delete anything. These days, teams of paralegals and attorneys engage in sophisticated and expensive pre-trial discovery for document requests. It is very easy to hire a forensic analyst to go into a computer and find out what has been modified, deleted, etc.

In many - perhaps even the majority - of cases we take to trial or arbitration these days, the outcome is significantly affected and sometimes determined by the content of one or two critically important emails, unearthed during our review of thousands of emails and documents produced in the course of the litigation. So, before you hit that Send key, picture a big yellow "CAUTION!" sticker over your screen and think before you send.

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