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A New Attorney’s Most Important Writing: Emails

Joseph Regalia

A New Attorney’s Most Important Writing: Emails

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As a young lawyer or intern, most attorneys will judge your lawyerly skills not by reading your appellate briefs or summary judgment motions—but by reading your emails. A young associate’s life is full of quick-and-dirty email assignments. Research questions for partners, summaries of documents—you will spend many days doing nothing more than shooting off emails. This means that your chance to impress others and develop strong relationships will often come down to whether you know how to craft a good one.

Emails are crucial for another reason: they are focused on another attorney’s specific need, often time-sensitive and dire. You can be sure that your reader will pay careful attention to every word. Sloppy style, poor organization, and loose reasoning won’t fly under the radar. And we are most likely to make these mistakes in quick electronic communications such as emails (let’s not even get started on Tweets).

But the good news is that emails don’t just train the spotlight on the bad; they’re also a chance to show off the good. You are on stage: highlight your writing and other professional skills. Show people your writing style, legal acumen, and ability to add value to projects and be a self-starter.

With the importance of emailing in mind, I offer you a list of best practices.

Ask Plenty of Questions

Whenever you get an email assignment, ask lots of questions about what is expected. What will your reader do with this information? How much time should you spend? How much information do they want? When do they want it by? What, exactly, are the questions you should answer? Are there any helpful places to start? Many young lawyers have been doomed when working on short and quick assignments by doing too little, too much, or simply the wrong work.

Subject Lines Are Crucial

Be thoughtful about subject lines and embedded text. If you are responding to a chain of emails, it might make sense to start a new email rather than lugging along all the baggage. Make sure your subject line tees up your email’s substance. If your email is time sensitive, say so in your subject line.

Err on the Side of Formality

Be mindful of the tone you strike in salutations and your signature block. Double-check that you spell the recipient’s name right—nothing is worse than calling Mr. Park Mrs. Park (Yes, I have done that before).

Add Value Now

In every email you send, consider whether there are any ways to add value to the task you were given. If it’s a research assignment, are there other resources or secondary sources you can attach? A few helpful cases? Don’t waste too much of your time, but this is a chance to show that you are self-motivated and look for ways to add value to projects (a rare trait in young attorneys and one that seasoned attorneys will notice).

Add Value Later

Offer some concrete next steps that you can take to help your reader further—don’t just do what you’re told and leave it at that. Think specifics, not an abstract “if I can do anything else, lemme know.” Offer to conduct specific follow-up research, track down an expert to get a second opinion—anything to show that you are thinking about future steps and the bigger picture.

Make Your Email User-Ready

When organizing your email, think about what your reader will be using it for:

  • If you are writing an email for a partner, and you know that the partner will forward your research to a client—consider putting soundbites in your email so the partner can copy and paste them into their own email.
  • If your partner uses your email as talking points for a conversation, consider offering suggested questions, sound bites, or bullet points.
  • Consider whether there are ways to organize, package, or format your writing so that it is tailored to your reader’s purpose.

Include a Summary

I suggest you start any substantive email with a summary of takeaways. Include:

  1. a bit of context to remind the reader what this email is about, why you are writing it, and what’s going on;
  2. the direct answers to any questions you were asked; and
  3. a summary of the most important takeaways. (If it’s legal research, what were the key holdings in a quick sentence or two? If it’s factual, what are the most crucial points you found?)

Include a Thorough Explanation

After your summary, provide a clearly-labeled section with a more thorough explanation of the issues. This allows your reader to choose their own adventure: if they want details, they can skip to the lengthy section. If they want the down-and-dirty, they can stick with the summary.

Organization Is Essential 

Your organization is crucial because your reader is likely to be in a hurry, but at the same time, you have to deliver information without all of the windup you get in a brief or memo. Should you tackle threshold issues first? Should you discuss more important issues before getting to the boring stuff? Is there a time-sensitive issue that needs your reader’s immediate attention?

Use White Space

Ninety-nine percent of dense emails are never read. That isn’t a real statistic, but it could be. Use white space, clear headings, bullet points, paragraphs, sections, and other devices to break up your writing.

Don't Take Shortcuts

Think deeply and carefully about any legal analysis you provide in an email. A brief or motion will likely be vetted by others before it’s used—and frankly, in many cases, emailed information is more crucial because it can be time sensitive. Emails are not the time to take shortcuts. Show your reader that you are detail-oriented, think carefully about the law, and know how to explain the law clearly.

Be Attentive to Your Writing Style

  • Typos are not an option in emails. Your reader will always notice.
  • You will be judged for every excess word and sentence—the last thing you want to do is waste a reader’s time.
  • Rewrite and rewrite until each sentence is as simple and direct as it can be. Your reader has no time to disentangle verbal gymnastics.
  • Use summary paragraphs to quickly narrow down questions or issues to what matters.
  • Use transitions and headings to connect up your writing on the sentence, paragraph, and section levels.
  • Use all of your other style tools to show off that you are a clear, articulate writer.

Answer the Question

Make sure you stick to the questions you were given or the goal of your email. Tangents are reader killers. You should always look to add value, as I explain below. But make sure you are adding useful value and not wasting your reader’s time.

Be Mindful of Your Tone 

Carefully consider the overall tone of your email. You don’t want to sound too stuffy, and you want to show off your clear, concise writing chops. But don’t make the mistake of being so chummy that your reader is taken aback. It is easy to misconstrue the tone of an email—your reader can’t see your face, hear the tone of your voice, or use any other cues to determine your emotion or mood. Make sure there is no way for your reader to hear something in your email that you didn’t mean to put there.

Don’t Become the Victim of a Reply-All Debacle

An easy trick is to start a new email when replying to someone and pasting in their address. Also, be thoughtful about who you are ccing and bccing.

If Your Email Is Negative, Sit on It for 24 Hours If Possible

There is nothing worse than email remorse.