How to Write a Kick-Ass Email

19 April, 2018

Ryan Anderson

Ryan Anderson


You hate them. You need them. You can’t do without them. They make your life easier and cause constant distractions. It’s time for attorneys to write better legal emails.


Last week the whole country started talking about attorney emails.

In the aftermath of the FBI raid on attorney Michael Cohen’s office, we learned that the Department of Justice had already been peeking in on his email accounts.

While the President tweeted that attorney-client privilege is dead, the DOJ insisted that the emails showed Cohen performed “little or no legal work.” And the rest of the country waited for more details about adult film stars.

Whatever happens with the Cohen chaos, attorneys shouldn’t need more motivation to learn how to write better legal emails.

Because these informal little time-sucks aren’t just tangents to your work. Sometimes they are your work. We need to take them seriously, and we need to do them right.

Here are 11 ways to write kick-ass legal emails, that will protect your clients, communicate clearly, and make you more likable.

PART I: Attorney-Client Privilege


Before we get to writing style, we need a few notes on attorney-client privilege. President Trump tweeted its death, but you have tools to keep yours alive.

1. Send it to the right person.

It’s obvious, right? But attorneys still fail to double-check the ‘to’ box. It’s especially dangerous now that email has that handy auto-complete ability.

So just look once more before you send it, ok?

Also swear off the ‘reply all’ button. Emails should always go to those who absolutely need to know what you’re saying. If you send your missive out to too large of a group, it’s much harder to argue that the information is confidential and privileged.

To help your clients avoid the ‘reply all’ mistake, don’t cc them on communication with opposing counsel. Forward that information to them separately.

2. Enable ‘Undo Send.’

It’s saved my bacon before! If you’ve got a Gmail account, click the little gear in the upper right. Hit ‘Settings.’ And then tick the box for ‘Enable Undo Send.’

Next time you feel that lurch in your stomach after you hit ‘send,’ you can immediately stop the process. This is useful not only when you’ve entered the wrong recipient, but also when you’ve spouted off something in angry all-caps (see #10 below).

Even if you only use this once, you’ll be grateful it’s there.

3. Have a quick response when you do mess up.

The moment you discover a mistake made by you or your client, work to make it right. Send a follow-up email. Call the accidental recipient if you can.

How can this help you? Take a look at cases like Charm v. Kohn. When a client twice replied-all to opposing counsel, the court decided (“perhaps with some indulgence for human fallibility”) that the email was still privileged. This is because the client’s attorneys had a quick response, demanding the opposing counsel delete the email.

4. Educate clients

Put on your teacher’s cap, because this is a lesson your clients need to learn. No matter how careful your emails are, your client can wreck it all. They need to understand that if they forward your email, it might lose its privileged status.

5. Make a good privilege log

Email has made a real mess for privilege logs. The dust hasn’t settled yet on the debate of how to best document the chaos. Do you have to log each email in a chain? Can you apply a categorical privilege claim to certain kinds of email, or do you have to explain them one-by-one? Often the answers depend on jurisdiction.

If the opposing counsel is asking for privileged emails, seek out an agreement with them. Often you can agree to streamline the logging process, whether by excluding categories of obviously privileged information or allowing some emails to be logged together.

Once you have an agreement, follow through. Learn a lesson from Muro v. Target Corp. A sloppy privilege log pushed the judge to demand that Target cough up many of its emails. Give your log the necessary detail, and get it in on time.

Also, consider using case management options that allow for good tracking of email communications.

6. Know when to Disclaim

The boilerplate email disclaimer has become a joke. For a full discussion on their failings, see this post.

Rather than automatically attaching a disclaimer at the bottom of every email, only use disclaimers when they’re relevant. And place them at the beginning of an email so they’re more likely to be read.

PART II: Writing Style


There’s more to emails than bare legal logistics.

You also want emails that communicate clearly. You want emails that make your clients like and trust you. You want emails that have style.

Here’s a few tips for that:

7. Write for Speed-readers.

People read differently online. It’s almost like we shouldn’t use that verb anymore. We should only call it ‘scanning.’

That makes the writer’s job harder. Attorneys are trained in using long sentences and boilerplate phrases. The best email writers will put that training aside and pick up some tips from bloggers, marketers, and other creators of digital content.

Put your most important information in the first sentence. After that, make the first sentence of each paragraph your ‘topic sentence.’ These not only give your speed-scanning clients the most important information — they also catch their attention and alert them to what’s inside the paragraph. And that makes it more likely your clients will slow down enough to read the whole thing.

8. Keep it short.

Short sentences. Short paragraphs. Lots of white space.

BUT:

9. Be personable.

I’ve met attorneys who are delightful in-person, but sound like a cardboard cut-out of themselves through email.

Email is this naturally informal medium, and attorneys are right to try to be cautious and give the act some formality (see Part I above). But you can be careful and professional without sounding like a law-bot.

Even just one warm greeting or one line expressing interest in the client as a human can go a long way. If you’re writing a longer piece, sprinkling in the client’s name can keep them engaged throughout and make it more likely they’ll actually read the whole thing.

10. Manage anger.

Watch those ALL-CAPS, buddy.

If you’re feeling heated, give yourself a cooling-off period. See if someone else on the legal team can draft the email. Write a draft and delete it. Just find some way to work through your feelings — and then come to the communication task at hand.

It’s your cool-headed precision that will build your practice, not the fire of your wrath.

11. Be responsive — but don’t let email rule you.

Your clients love quick responses. But constantly checking and answering emails is a nightmare. It keeps your brain in a perpetual state of distraction. It swallows your work day. It takes control of your to-do list. (If you’re not already nodding along to this, read here.)

How can you please your clients without letting email sap your soul?

You might want to get some help.

Spread the email-checking duties across a legal team. If the email is immediately documented in the case notes (or is sent directly into the client’s case file, as you can do with Filevine), then another member of the legal team can send a quick response. A paralegal might be able to answer their question. But even if not, a staff member could send a note acknowledging they received the client’s email, and tell them a full response will come by a specific time in the future. The staff member can then assign a task (with a deadline) to the necessary attorney, telling them to respond in full at a time when it doesn’t interrupt their other work.

Another option is to schedule in your email-checking time. Instead of interrupting a task, only check and respond to emails once you’ve finished. It takes Herculean discipline not to self-interrupt, but it’s worth it.

No more excuses; the time for those has past. Go, and write better legal emails!