The Seven Deadly Sins of e-Mail

We've all heard horror stories about e-mails that have become trial exhibits – blown up on giant placards or projected on a large screen in front of a jury. The earnest words your client typed in private suddenly take on unforeseen importance when, months or years later, a dispute develops and a trial is held. Like a major league pitcher who releases a hanging curveball to the reigning home-run champ, your client would probably like to “take back” an e-mail that bashes a client, admits incompetence or pitches pent-up emotions in a cathartic rage.

Too Late

The damage was done as soon as the send button was pressed. Copies of the future trial exhibit are lodged in an e-mail server, one or more inboxes, several back-up tapes and maybe even hard files. Discovery will bring the e-mail to the surface, and the spotlight of litigation will ensure the author never forgets the meaning of regret.

We need not, however, simply succumb to the temptation of e-mail. e-Mail mistakes can be avoided. Clients just need to be educated on how to prevent e-mail mistakes. Although common sense can't be taught, several specific types of e-mailing behavior should be avoided. E-mailers commit what we'll call here the Seven Deadly Sins of e-Mail. While it's unlikely we'll all steer completely clear of these sins, all e-mailers should make every effort to avoid committing the Seven Deadly Sins.

Sin #1
The Flippant e-Mail

Short, sweet and deadly, the Flippant e-Mail is often a case of oversimplification. Corporate employees are often under extraordinary pressure to “keep it simple.” Unfortunately, this approach is often the kiss of death in any subsequent litigation. An offhand, glib or dismissive remark that the author unequivocally understands might not be copacetic without surrounding context.

For instance, use of casual ' even conversational tone ' in e-mail may be an effective way to communicate in the near term, but any flippant remark revisited months, even years, later is potentially lethal to a legal position. In a case where the disappointed buyer of a business computer system challenged the ability of the system's vendor to implement the system, the disappointed buyer was able to craft an entire case around an e-mail stating that a certain aspect of the software system “would not work.” This simple and direct statement grossly simplified a very complex situation, where the software would in fact “work” so long as certain assumptions were met. But without a contemporaneous written explanation of the assumptions, the vendor faced a significant hurdle in trying to explain away the incomplete communication.

And consider this: A single word authored by a corporate employee effectively destroyed the defense of a corporation alleged to have violated the payment obligations of a royalty contract. When an employee summarized the content of his employer's royalty database as “crap,” all questions about the integrity of the data in the database were resolved against his employer.

Sin #2
The Emotional Release e-Mail

Perhaps the e-mailer's worst sin, the Emotional Release e-Mail is temporarily gratifying, but ultimately unfulfilling. For better or for worse, many people use e-mail to express emotions they are experiencing. Indeed, the writing process serves a channeling function, allowing the author an opportunity to sort out issues and emotions. As a result, sentences and paragraphs filled with some of our less noble emotions are forever fixed in a written form that is extraordinarily difficult to erase. Rage, vindictiveness and anger are often expressed in heartfelt e-mails crafted by people who never stop to consider how those words may look removed from all context.

For example, insulting the sexual orientation of another party to a contract might have felt good at the time an e-mail in a recent case was authored. But airing the bigoted statement during litigation over that contract did nothing to build the author's credibility.

Sin #3
The Jailhouse Lawyer e-Mail

In a civilized society where the rule of law prevails, nonlawyers must try to do without adequate education in the finer points of law. As a result, thousands of Jailhouse Lawyer e-Mails are created every day and sent by people who have no business opining on the Sherman Antitrust Act, the enforceability of covenants not to compete or the scope of a patent. Consequently, individuals are creating evidence that confounds counsel trying to preserve a defense or prove the existence of a cause of action. Information is power in litigation and e-mails that reach legal conclusions without the benefit of complete information, much less the advice of counsel, often dramatically affect the outcome of a dispute.

In one e-mail, an individual essentially conceded liability for payment of a contract's liquidated damages provision. His later defense that he was not in breach of the complicated agreement rang hollow to an arbitrator who seized on the legal conclusion drawn by the layperson. Likewise, the statement in an e-mail, “Do you expect our late start will trigger any penalties under the current contract terms?” sure seems to be an admission that the author believed his organization was responsible for delay penalties under the contract.

Sin #4
The Out of Character e-Mail

Corporate employees are all role-players in a drama that is larger than any one of them. Occasionally, a player slips and sends an Out of Character e-Mail, revealing that he or she is a person with allegiances and loyalties to something other than his or her employer. As a result, e-mails revealing personal bias, attitudes and motivations create unnecessary conflicts that require significant spin control in subsequent litigation.

For example, a salesman who brags about a commission that is so large it would pay for his child's college education found it very difficult to present himself as selflessly solving his customers' problems through their purchase of his employer's products and services. Similarly, it was hard to explain an e-mail in which a project manager stated to his superior that he told the company's customer “schedules were impacted by [A and B's] unexpected absences.” “This isn't totally true,” the e-mail continued, “but we can still use it.” The project manager was no longer able to present himself as an advocate for the client's objectives.

Sin #5
The Mea Culpa e-Mail

Judging by the number of e-mails in which people admit to imperfection, the early and often confession of sin is apparently rewarded in corporate America. The Mea Culpa e-Mail usually seeks to increase the author's storehouse of credibility or legitimacy by owning up to mistakes and failures. The temporary gain in credibility, however, is frequently offset by the destruction of legal rights resulting from such an admission. One person's magnanimous statement is another party's admission of a party opponent.

An e-mail confessing that a company's computer programmers were producing a “volume of bugs” might have effectively explained delays in a software-development project, but it seriously impaired the company's ability to convince an arbitrator that the customer's continual modifications to the project blueprint were the true cause of the delays.

Sin #6
The Late Night e-Mail

During an interrogation at a police station, detectives are generous with water and stingy with trips to the bathroom because the interviewee is likely to be more forthcoming with information if he or she is focused on leaving the room as soon as possible. Similarly, corporate employees who are working late are much more likely to imprudently divulge information in an e-mail stamped 8:35 p.m. than one time-stamped 8:35 a.m. The dreaded Late Night e-Mail often contains statements that a less-harried person with more time to think would never dream of committing to written form.

The world is filled with complex, layered questions. Sometimes, there's just not enough time to compose and proofread a complete, comprehensive and detailed answer. As a result, an oversimplified answer is drafted and dashed off in a late-night flurry of e-mails. A sure sign of a tired and rushed mind is a long-winded e-mail containing a paragraph toward the bottom that begins, “As long as I'm on a roll, I am not in favor of breaking the contract.” Perhaps after regular work hours, an increase occurs in the already inflated sense of security authors have with e-mails.

Sin #7
The Sarcastic e-Mail

Sarcasm is extremely difficult to convey in e-mail. Nevertheless, the Sarcastic e-Mail is nearly ubiquitous in corporate America. Not even an awful employment market has reduced the number of mocking, sardonic and satirical e-mails being drafted every day. A wry sense of humor might be entertaining in the workplace, but judges and juries are not as kind an audience.

A rather sarcastic e-mail became public in recent proceedings between federal and state regulators, and the major Wall Street investment banks arising from charges that the investment banks tailored research reports and stock ratings to secure and retain investment banking clients. A stock analyst at an ostensibly unbiased bank e-mailed an unpublished stock report on Tyco International Ltd. to a Tyco executive with a cover note that read: “Please review ASAP. I will not send it out until I hear from you first! Loyal Tyco employee.” The tongue-in-cheek closing of the e-mail demonstrated in plain terms that the research report was not an objective opinion, but rather the product of a symbiotic relationship between an investment bank and the company covered by the bank's research analysts.

So, Remember This …

Most “bad” e-mails are the product of a lapse of common sense. But it's futile to try to teach our clients to conduct themselves with more common sense when composing e-mail. We are far more likely to reduce the number of e-mails that become trial exhibits by explaining the Seven Deadly Sins of e-Mail. Armed with the knowledge of the behavior that needs to be avoided, our clients can – we hope – avoid the temptation that presents itself with each of the 6 billion e-mails sent every day.

We've all heard horror stories about e-mails that have become trial exhibits – blown up on giant placards or projected on a large screen in front of a jury. The earnest words your client typed in private suddenly take on unforeseen importance when, months or years later, a dispute develops and a trial is held. Like a major league pitcher who releases a hanging curveball to the reigning home-run champ, your client would probably like to “take back” an e-mail that bashes a client, admits incompetence or pitches pent-up emotions in a cathartic rage.

Too Late

The damage was done as soon as the send button was pressed. Copies of the future trial exhibit are lodged in an e-mail server, one or more inboxes, several back-up tapes and maybe even hard files. Discovery will bring the e-mail to the surface, and the spotlight of litigation will ensure the author never forgets the meaning of regret.

We need not, however, simply succumb to the temptation of e-mail. e-Mail mistakes can be avoided. Clients just need to be educated on how to prevent e-mail mistakes. Although common sense can't be taught, several specific types of e-mailing behavior should be avoided. E-mailers commit what we'll call here the Seven Deadly Sins of e-Mail. While it's unlikely we'll all steer completely clear of these sins, all e-mailers should make every effort to avoid committing the Seven Deadly Sins.

Sin #1
The Flippant e-Mail

Short, sweet and deadly, the Flippant e-Mail is often a case of oversimplification. Corporate employees are often under extraordinary pressure to “keep it simple.” Unfortunately, this approach is often the kiss of death in any subsequent litigation. An offhand, glib or dismissive remark that the author unequivocally understands might not be copacetic without surrounding context.

For instance, use of casual ' even conversational tone ' in e-mail may be an effective way to communicate in the near term, but any flippant remark revisited months, even years, later is potentially lethal to a legal position. In a case where the disappointed buyer of a business computer system challenged the ability of the system's vendor to implement the system, the disappointed buyer was able to craft an entire case around an e-mail stating that a certain aspect of the software system “would not work.” This simple and direct statement grossly simplified a very complex situation, where the software would in fact “work” so long as certain assumptions were met. But without a contemporaneous written explanation of the assumptions, the vendor faced a significant hurdle in trying to explain away the incomplete communication.

And consider this: A single word authored by a corporate employee effectively destroyed the defense of a corporation alleged to have violated the payment obligations of a royalty contract. When an employee summarized the content of his employer's royalty database as “crap,” all questions about the integrity of the data in the database were resolved against his employer.

Sin #2
The Emotional Release e-Mail

Perhaps the e-mailer's worst sin, the Emotional Release e-Mail is temporarily gratifying, but ultimately unfulfilling. For better or for worse, many people use e-mail to express emotions they are experiencing. Indeed, the writing process serves a channeling function, allowing the author an opportunity to sort out issues and emotions. As a result, sentences and paragraphs filled with some of our less noble emotions are forever fixed in a written form that is extraordinarily difficult to erase. Rage, vindictiveness and anger are often expressed in heartfelt e-mails crafted by people who never stop to consider how those words may look removed from all context.

For example, insulting the sexual orientation of another party to a contract might have felt good at the time an e-mail in a recent case was authored. But airing the bigoted statement during litigation over that contract did nothing to build the author's credibility.

Sin #3
The Jailhouse Lawyer e-Mail

In a civilized society where the rule of law prevails, nonlawyers must try to do without adequate education in the finer points of law. As a result, thousands of Jailhouse Lawyer e-Mails are created every day and sent by people who have no business opining on the Sherman Antitrust Act, the enforceability of covenants not to compete or the scope of a patent. Consequently, individuals are creating evidence that confounds counsel trying to preserve a defense or prove the existence of a cause of action. Information is power in litigation and e-mails that reach legal conclusions without the benefit of complete information, much less the advice of counsel, often dramatically affect the outcome of a dispute.

In one e-mail, an individual essentially conceded liability for payment of a contract's liquidated damages provision. His later defense that he was not in breach of the complicated agreement rang hollow to an arbitrator who seized on the legal conclusion drawn by the layperson. Likewise, the statement in an e-mail, “Do you expect our late start will trigger any penalties under the current contract terms?” sure seems to be an admission that the author believed his organization was responsible for delay penalties under the contract.

Sin #4
The Out of Character e-Mail

Corporate employees are all role-players in a drama that is larger than any one of them. Occasionally, a player slips and sends an Out of Character e-Mail, revealing that he or she is a person with allegiances and loyalties to something other than his or her employer. As a result, e-mails revealing personal bias, attitudes and motivations create unnecessary conflicts that require significant spin control in subsequent litigation.

For example, a salesman who brags about a commission that is so large it would pay for his child's college education found it very difficult to present himself as selflessly solving his customers' problems through their purchase of his employer's products and services. Similarly, it was hard to explain an e-mail in which a project manager stated to his superior that he told the company's customer “schedules were impacted by [A and B's] unexpected absences.” “This isn't totally true,” the e-mail continued, “but we can still use it.” The project manager was no longer able to present himself as an advocate for the client's objectives.

Sin #5
The Mea Culpa e-Mail

Judging by the number of e-mails in which people admit to imperfection, the early and often confession of sin is apparently rewarded in corporate America. The Mea Culpa e-Mail usually seeks to increase the author's storehouse of credibility or legitimacy by owning up to mistakes and failures. The temporary gain in credibility, however, is frequently offset by the destruction of legal rights resulting from such an admission. One person's magnanimous statement is another party's admission of a party opponent.

An e-mail confessing that a company's computer programmers were producing a “volume of bugs” might have effectively explained delays in a software-development project, but it seriously impaired the company's ability to convince an arbitrator that the customer's continual modifications to the project blueprint were the true cause of the delays.

Sin #6
The Late Night e-Mail

During an interrogation at a police station, detectives are generous with water and stingy with trips to the bathroom because the interviewee is likely to be more forthcoming with information if he or she is focused on leaving the room as soon as possible. Similarly, corporate employees who are working late are much more likely to imprudently divulge information in an e-mail stamped 8:35 p.m. than one time-stamped 8:35 a.m. The dreaded Late Night e-Mail often contains statements that a less-harried person with more time to think would never dream of committing to written form.

The world is filled with complex, layered questions. Sometimes, there's just not enough time to compose and proofread a complete, comprehensive and detailed answer. As a result, an oversimplified answer is drafted and dashed off in a late-night flurry of e-mails. A sure sign of a tired and rushed mind is a long-winded e-mail containing a paragraph toward the bottom that begins, “As long as I'm on a roll, I am not in favor of breaking the contract.” Perhaps after regular work hours, an increase occurs in the already inflated sense of security authors have with e-mails.

Sin #7
The Sarcastic e-Mail

Sarcasm is extremely difficult to convey in e-mail. Nevertheless, the Sarcastic e-Mail is nearly ubiquitous in corporate America. Not even an awful employment market has reduced the number of mocking, sardonic and satirical e-mails being drafted every day. A wry sense of humor might be entertaining in the workplace, but judges and juries are not as kind an audience.

A rather sarcastic e-mail became public in recent proceedings between federal and state regulators, and the major Wall Street investment banks arising from charges that the investment banks tailored research reports and stock ratings to secure and retain investment banking clients. A stock analyst at an ostensibly unbiased bank e-mailed an unpublished stock report on Tyco International Ltd. to a Tyco executive with a cover note that read: “Please review ASAP. I will not send it out until I hear from you first! Loyal Tyco employee.” The tongue-in-cheek closing of the e-mail demonstrated in plain terms that the research report was not an objective opinion, but rather the product of a symbiotic relationship between an investment bank and the company covered by the bank's research analysts.

So, Remember This …

Most “bad” e-mails are the product of a lapse of common sense. But it's futile to try to teach our clients to conduct themselves with more common sense when composing e-mail. We are far more likely to reduce the number of e-mails that become trial exhibits by explaining the Seven Deadly Sins of e-Mail. Armed with the knowledge of the behavior that needs to be avoided, our clients can – we hope – avoid the temptation that presents itself with each of the 6 billion e-mails sent every day.