Email prophylaxis for dummies: How not to end up trying to explain to a judge what your email really meant

“Give me six lines written by the most honest man, and I will find enough in there to hang him,” said Cardinal Richelieu, back in the 16th century. (Probably.)

We’ve all seen the revelations gleaned from the hacks of Hillary Clinton’s email, John Podesta’s email and General Colin Powell’s email, among others. What has come to light made my jaw drop – not because it reveals wrongdoing or illegality, but because people in those positions should have known email’s cardinal rule: Don’t write anything in email you don’t want to see on the front page of the New York Times.

This is what we were always taught in the insanely litigious business of healthcare. We were told: read your email through and picture it in the newspaper with your photograph right above it. We were given training on what could be said by email and what should be said in person or on the phone. Here is some of that advice, as well as lessons I learned the hard way. It’s mostly targeted at work emails, but your personal emails could probably do with a review. For example, have you heard of “divorce”? Sometimes computer contents and emails are discoverable during divorce proceedings. A lot of this advice goes for other written communication as well, be it texts, chats or messaging. (Please note this is not legal advice – I am not a lawyer.)

As you read through your emails prior to sending them, bear in mind that a nosy newspaper reader could the least of your worries. Imagine it is being read out loud by a hostile attorney in court. Emails can be, and often are, subject to subpoena, which means they are read (and interpreted without you present) by someone with an incentive to infer the worst possible meaning in something you thought was innocuous.

People often think of emails as completely informal, a sort of everyday talking that magically goes through office walls. This isn’t the case. Many companies have regulations or consent decrees that require them to keep emails for a number of years, and even ones that don’t have regulations tend to keep them around for months or longer. Deleting them from your inbox or sent mail does not delete them from the sender or recipient’s mailbox, and most likely the company, or your cable provider, will keep a copy on their server, so even if the sender and recipients all collude to delete the email, it’s still there, in cyberspace. And then you will be accused of attempting to destroy evidence on top of everything else.

Generally speaking, your company has the right to read any emails that pass through its server – so if you write your bestie in Warehouse about your pick in soon-to-be-mom Valentina’s due-date pool and you make an off-color remark about pregnant women, bear in mind you’re a) illegally betting *and* b) giving the impression you foster a hostile work environment - and your boss can legally read the email from the company server, if they so choose.

If you get your company emails on your own smartphone, check with your company lawyer and get advice on obtaining a work-only phone, as mixing emails may make your entire device – including your Tinder account among other things – subject to subpoena if the company does something untoward.

Since emails are written records, avoid slang and informal writing. Even if it's not company policy, it’s worth putting a “Dear recipient” up top and a “Best regards” at the bottom, if only to remind yourself that you’ve actually written a letter, not yelled something over the top of your cubicle to your golf buddy. Try to compose whole sentences and read them back to see if they still mean what you thought they meant. Occasionally a missing comma or a missing “not”, a double negative or overnegation will alter the meaning. (For example, “It’s impossible to underestimate the impact Larry has had on the company” means that it’s not possible to say how little Larry is worth. That may not be what you meant. Even a hostile lawyer may not be able to make this stick in court, but it will get you laughed at and Larry may feel you did it on purpose…)

Don’t write things that put you, or your company, in a bad light. “This is the third time Fred has screwed up and nobody ever does anything.” Read what you wrote and imagine it in the first paragraph of a Time Magazine expose. Did you really mean to open your company up to a negligence lawsuit? If not, but Fred really is screwing up, pick up the phone, or walk over, and talk to him instead. Or his boss. Or HR. Whatever. Unless you have exhausted other avenues and really believe you now have to put your frustration in writing, don’t email it. If you are a healthcare boss and you get this email, ask yourself if the writer is genuinely trying to help or if he’s setting himself up for a cool couple of mil in whistleblower awards down the line.

Don’t suggest anything illegal, even if you know, and the recipient knows, you’re just being sarcastic or having fun. “He won employee of the month again. Maybe we should just take Simon out…” What does that mean? Kill him, plot to get him fired? Hostile lawyers don’t know what jokes are. Don’t email jokes.

Bear in mind the structure of emails. They have a header, which you probably never see, but techy types can and they tell lawyers and investigators a lot about the sender, recipients, dates and contents. Emails have a subject line, then the body of the email and, quite often if they’re a reply, a quote of the original email at the bottom. A quote. In plain text. Not an attachment, but just the text of what was originally written.

When the sh1t hits the fan, an email will often start getting replied to, forwarded, and sent to new recipients very rapidly. If something terrible is happening – let’s say, someone has lost a newborn baby’s blood specimen – an email with a subject line like “Baby 19089132 sample missing” starts making the rounds. All the problem solvers receive the email, and they each reply. Some invariably hit “reply all” and everyone who received the first email will know what they found. Some will reply only to the initiator or to coordinators. The coordinators will receive some emails but not others, and reply to them. Each will use "reply all" or reply to their favored list of problem solvers, depending on their whim. This means that a few hours into a crisis there could be several hundred emails with the subject line “Baby 19089132 sample missing”, and some of them will contain an indented chain of the text of every email that was sent with that subject line, some will contain most of it, and some will contain a different selection of most of the emails with that subject line. Now imagine that someone about third way down the list in company importance gets a subpoena and whichever one of these email chains she received is the one that ends up in court. Will it tell the whole story? (No, obviously.)

Bear in mind that also, if Baby 19089132 was from Client 6308, it’s quite likely that the next time someone mislays a sample from Client 6308, in order to stress the importance of why we shouldn’t frak off this client yet again, the initiator/coordinator will simply find the original email - “Baby 19089132 sample missing” – write their new complaint at the top (of whichever version of the chain they received) and send it around again. Even if it’s a year later.

So “Baby 19089132 sample missing” may refer to JSH-20310269’s sample being missing a year later and not contain complete information about either. And to make it more complicated, most email programs allow you to change the subject line, delete included emails, add other emails you think are interesting into the middle of the mélange, and even, should you be so inclined, allow you to change any of the text without marking it as changed.

You may have to defend what it appears you wrote about a missing sample in court. Good luck. Hope you didn’t delete any emails from the chain you thought was too long and rambling, add any you thought were informative, or make any remarks about film stars’ asses or change Baltimore area coordinator Matt Hunt’s first name to Mike halfway down a five-page chain because it was très funny and he’d never see it… for the whole year it was careening between servers.

Also, try not to have a common name. My given first name is common enough that there were 23 of us in our company. I’ve had to sit with “our” attorneys working out whether I’m the person referred to in each one of the discovery emails or whether it was one of the other 22, and that was a lot of fun, too.

Companies often use a technique called “brainstorming” where you put every idea you think of on a whiteboard. The coordinator will say, “There’s no such thing as a bad idea!” That’s true on a whiteboard. In email, don’t write down all your bad ideas, unless they’re labeled “bad ideas”.

Bear in mind a lot of email apps have a "BCC" function. It means blind carbon copy for reasons lost in the mists of time, but what it does is send a copy of the email to a person not on the "to" line or on the "CC" line. When you receive an email you can see who it has been sent to besides yourself - except for any BCC recipients. Only the sender knows who else got it. You think your boss isn't in on the conversation? She might be - she might be being BCC'd.  And your return emails may be being forwarded to her without your knowledge. And even more likely, your emails are being sent to Saks Fifth Avenue credit card help desk, because your recipient just tried to forward it to the warehouse guy, whose name is Saxon, Andrew, from their email address list, got it nearly right and didn't read it before sending, due to not having read my helpful advice.

Your company may have a way of classifying private or secure emails. If they do, follow it. In may involve putting a (c) in the subject line and a long thing in the footer of an email (sometimes called the signature file) that states the email was confidential, intended only for the person named in the “to” line and if you are some random guy who got hold of it by accident, you should contact the company and delete the email. I refer you to your company attorney about what to use and whether it is actually binding. You should be aware, however, that if you and RivalCo have a sanctioned, legal email conversation back and forth, the footer of the email could fill up with two, four, six, eight iterations of your and their confidentiality notice as the thread progresses. What might this mean? Your attorney will be happy to discuss this question. And remember that no matter how many confidential notices may have stacked up at the bottom there, it won’t stop Jeff in Purchasing from forwarding the whole five-page long shebang to RivalCo’s entire hundred-strong accounts payable department by accident, while trying to find and attach a recipe for eel pie and send it to his wife.

Lastly, attorney-client privilege. Discussions between you and your attorney are private, and can’t be used in court. Your attorney, or your company attorney, can give you some wording to put in the subject line and in the body of your email that privileges the email in this way. It will be something like, “Attorney-Client Privileged Communication”.

Even so, if you and your attorney are working on a document and you attach the draft to the email, it isn’t covered by an email subject line privilege statement, and it should contain its own wording, along the lines of “Attorney-Client Privileged Work Product” as a header inside the document. Check with your attorney what wording you should use.

If you fail to privilege a communication properly, expect it to be read out in court. On the other hand, if you’re just spit-balling some stuff that might not pass legal muster and sending it to your boss, don’t think that putting your company attorney on the “cc” line and adding “Attorney-Client Privilege” to the subject line will protect you. For obvious reasons, the law requires you to be actually communicating with the lawyer before you claim attorney-client privilege. You should maybe ask them before you start with the cc’ing. 

Sometimes, emails and/or attachments sent to government agencies will be sent out to anyone requesting to see them through the FOIA (Freedom of Information Act.) If your emails and their attachments are confidential, discuss this with the agency over the phone and find out what confidentiality wording will prevent them doing this. You don't want to lose a patent because you emailed your invention at their request to the government, and RivalCo got hold of it.

Here’s some examples of problematic statements.

Jim says his team is behind schedule because Tanya is acting like a child again and not freeing up IT resources.

What you meant: The status report is being sent to Tanya’s ex and you wanted to curry favor with him by pointedly wording your status report. How this reads: Your company is dysfunctional and its processes are broken. If your customer sues you, this isn’t going to go well.

Nightbat, Inc. are developing the same sort of device Jim and Dave are working on.

What you meant: You read something on a Reddit Ask Me Anything and put two and two together. How this reads: You are performing industrial espionage and you’ll be lucky to find employment in future.

If Jack does that again, I’ll get mad. These things put patients at risk!

What you meant: You should tell Jack how important his role is in patient safety. How this reads: Jack has already put a patient at risk and looks like nobody did anything about it at the time. Please sue my company for negligence.

Remember: Would it look good on the front page of the New York Times with your picture above it?

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Here is an article by Micah Lee on email security, passwords and that type of thing. Useful for personal emails, but may not be possible for work emails.