What Was I Thinking? 10 Tips to Avoid eMail Disaster

EmailOne of the most significant ways we are judged today is how we write e-mails. No longer are we subject to scores of phone calls or face-to-face meetings. Technology has completely revolutionized the way we communicate. It’s an email world out there and how you present yourself can make or break your career.

While it’s a magnificent tool for communicating, email can be very damaging when used inappropriately. Too often we take the easy and quite candidly, cowardly, option of using email to avoid the emotional discomfort of a real time conversation. 

While it’s a magnificent tool for communicating, email can be very damaging when used inappropriately. Too often we take the easy and quite candidly, cowardly, option of using email to avoid the emotional discomfort of a real time conversation.
When it comes to communicating matters that can be uncomfortable or emotionally sensitive, nothing can ever replace a good old fashioned, face-to-face conversation.

To hide behind your computer screen, not only lacks courage and professional courtesy but can become very costly. Lack of sensitivity combined with misinterpretation can risk permanent damage to your career, not to mention damage to someone else. Time spent on damage control can be very detrimental. Often, we try dashing off a quick and often poorly worded written message trying to redeem ourselves. Trust me, the damage has been done.

Why do people use email as a method for “saying what they really think?” The more distance we have from someone, the more likely we are to make decisions in a cold, purely cognitive way. It’s easier than speaking to someone face-to-face. In reality, we think we will have fewer emotions to deal with.

A recent study out of University of Massachusetts-Amherst found that the farther away people are from the person they were communicating with, either physically or psychologically, the more apt they are to lie or exaggerate. Those communicating via email lied about five times more than those speaking face-to-face, whereas those using instant messaging lied about three times more than those talking face-to-face.

We have all been in situations where we get upset upon receiving certain emails; an incident occurs; we are angered or upset by someone’s actions. The tendency to dash off an email immediately is tempting. However, once you hit the Send button, you can never retrieve that email. No amount of deleting will help. Once it’s out in email land, it’s there permanently. Let us not also forget that the email is permanently on your hard drive. The email is discoverable. That is the essence of eDiscovery and computer forensics.

If you find yourself writing in anger, save a draft, go get some chocolate, and imagine that tomorrow morning someone has taped your email outside your door. Would your colleagues and supervisors be shocked by your language or attitude?

Here’s an example of the “Uh-oh” email:

“I was just made aware that John was promoted to Litigation Support Manager. While I am not offering up “sour grapes” because I did not receive the promotion instead (although as you know, I am very qualified for the position), I wanted to confidentially make sure you are aware that John has been fired twice off previous jobs.”

The damage to John’s career is horrendous. However, it can be nothing compared with the damage to yours. This is an email that should have never gone out.

Responding to angry emails.

When you receive angry emails, instead of responding in kind, take a rational approach.

From: James Jones
Subject: Ongoing document production
I have been trying to get in touch with you all day. I am having problems on this project. Don’t you check your emails? I’m not that well-trained here. The least you can do is explain in more detail how to do this.

If your recipient has just attacked you with an angry message, rather than reply with a point-by-point rebuttal, you can always respond with a brief note that:

a) Casually invokes the name of someone the angry correspondent is likely to respect (to diffuse any personal antagonism that may otherwise have developed) and
b) Refocuses the conversation on solutions and lessens the risk of escalating the situation into an all-and-all email war.

From: Jane Smith
Subject: Ongoing problems with document production

Since you told Sue you didn’t need extra training, I cancelled the Tuesday session. I can CC Sue since she will have to approve the training if we reschedule. In the interim, I can loan you copies of the manual or we can shift the indexing to someone else. Let me know your thoughts.

Three times you should never use e-mail.

1. When you are angry. Anger can trigger stress hormones and in turn, decrease our ability to communicate well. Never send an email when you are angry. Do whatever you need to get it out of your system. Just don’t hit “Send” while you’re still angry. Wait at least two hours to calm down, rationalize and see the whole picture. This gives you time to decide the most constructive way to convey that you’re upset. Emailing someone when you are raging is almost guaranteed to end in disaster.

2. When you are rebuking or criticizing. Too often we get a false sense of bravado and say things via email we would never have the courage to say in person. Delivering or receiving a rebuke or criticism isn’t easy for anyone. Save it for the face-to-face meeting or phone conversation. By providing feedback in person, you can read visual cues and immediately address any concerns the other person might have without things getting out of hand.

3. If there’s even a slight chance your words can be misunderstood. Emails can be interpreted in a myriad of ways – some of which you never would have anticipated. Your reader may be particularly defensive about certain issues. Save yourself time in damage control and possible lawsuits. Pick up the phone or meet them face-to-face to ensure that they hear your message in the most positive way.

Don’t have the conversation in a confrontational way, but in a way that says “you seem to be upset, perhaps we should talk this through." While not always comfortable, a phone call or face-to-face meeting provides an opportunity for meaningful dialogue that is difficult via email and could easily otherwise escalate the situation.

Don’t assume privacy or confidentiality.
Email is not secure. There is no such thing as privacy when it comes to email. A curious hacker, a malicious criminal, and your IT department can probably read any of your email messages in your work account. The email can be forwarded to others without your knowledge.

Show respect and restraint.
Many a flame war has been started by someone who hit “reply all” instead of “reply.” Most people know that email is not private. It is good form to ask the sender before forwarding a personal message. If someone emails you a request, it is perfectly acceptable to forward the request to a person who can help — but forwarding a message so that you can ridicule or humiliate the sender is just tacky.

Use BCC instead of CC when sending sensitive information to large groups. (For example, an employer telling unsuccessful candidates that they have been rejected for a position.) The name of everyone in the CC list goes out with the message, but the names of people on the BCC list are hidden.

10 Top Etiquette Rules

Now that we’ve covered writing emails in anger, let’s explore email etiquette that can help you get better responses and present you in a positive leadership role. Here are some guidelines to maintain good working relationships.

1. Keep the message focused using short paragraphs.
Why are you writing? It’s best to keep to one topic and use short paragraphs. Long emails with multiple topics are no longer taken seriously. Separate by blank lines. Everyone skims content these days. Most people find unbroken blocks of text boring or intimidating. Format your message for the ease of your reader. Remember that most email is read on mobile devices, Keep emails to five – ten sentences.

2. Stay organized.
Some readers will get partway through a complex message, hit “reply” as soon as they have something to contribute, and forget to read the rest. That’s human nature.

Number your points in more complex message. Split unrelated points into separate, purposeful emails. If you send all your readers a message that only relates to some of them, a good deal of readers waste time reading the whole thing to determine whether any part applies to them. Other people give up as soon as they find few details apply to them.

2. Use politeness.
My mother used to tell me “You catch more flies with honey than vinegar.” She was right. Please and thank-you are still important, but wordiness wastes your reader’s time (which is rude).

Indirect and waste of time: Hello Ron: I would very much like it if, at your earliest convenience, you could send the current password for the website. I look forward to your reply. Have a wonderful day!

Blunt and almost to the point of rudeness: “Need password for the website immediately.”
If you get a message like this, you might assume the sender trusts you and really needs your help. On the other hand, if you send a message like this, you are likely to appear needy and panicky. How do you want to come across?

Urgent, yet polite: The site is down. I can’t fix it without the new password. Can you forward it? Thanks.

4. Don’t send or forward emails containing libelous, defamatory, offensive, racist or obscene remarks.
You can put yourself or your firm at risk. You could be sued for simply passing something along, even if you aren’t the original author. Remember that company e-mail isn’t private. You have no legal protection.

5. Avoid attachments whenever possible.
Rather than forcing your reader to download an attachment and open it in a separate program, you will probably get faster results if you just copy and paste the most important part of the document into the body of your message.

Not good:
To: Everyone involved in Document Productions
From: Eager Paralegal
Subject: Helpful Handbook

Hello Everyone:
I’ve attached a PDF that I think you will all find useful. This is the fourth time I’ve sent the file – the version yesterday had a typo on page 215. Let me know what you think!

o Huge honking file.pdf (375 MB)
o Bigger cover letter

Okay, don’t everyone raise your hands – how many of you would read this or better yet, delete it without looking at any “attachments”? You betcha.

Hello Brenda:
I came across some tips on streamlining the document production process. Has anyone at your office volunteered to present at the paralegal workshop next month? If you’d like, I can do a 20 minute presentation. I can also send you the entire handbook if you would like.

Table of Contents:
1. Indexing documents
2. Notices to parties
3. Useful and effective software
6. Identify yourself clearly.

If you telephoned someone outside your closest circle who wouldn’t recognize your voice, you would most likely say something like “Hello, Jennifer. This is Chere Estrin from Estrin Legal Staffing.” A formal “Dear Ms. Green” salutation is not necessary for routine workplace communication.

7. Write a short and action-oriented subject line.
Never leave the subject line blank. Limit it to eight or fewer words. Mobile devices can cut off part of the text. Indicate if you need a response by a certain date, so your reader can prioritize the requests he or she is receiving that day.

8. Always include a signature line.
Frankly, nothing annoys me more than receiving an email without a signature line. The sender is assuming I know who they are by their email address. Are you kidding? Have you any idea how many emails I deal with daily?

9. Avoid jokes.
Because we're so accustomed to communicating via texts and social media, we might be less formal than we should in important emails. However, sarcasm can often be lost in email translation. Be careful not to include anything that can be misconstrued. Don't leave your message up for interpretation.

10. Make it easy to respond.
Remember that not responding is often a convenient alternative. While it is hard to force a response, at least you can prod. Make it clear, from the very first sentence, why you are writing and what you expect. You should not be writing mystery novels.

Make it easy for readers to respond by providing a default option. For example, you might say: “Unless I hear from you by Tuesday, I will assume that you want to proceed.”

Defaults are powerful because readers are not always willing to spend a lot of effort coming up with other options. The choice for the default option is especially hard to resist if you suggest that yours is the norm or recommended choice. If there are no easy options, you can specifically state that you expect a response. You can ask them to let you know what they intend to do, by when, and how. You’ll get better responses and start being viewed as a leader with solutions.

Above all, remember that you are representing the firm. How you write your personal emails is your business. However, it is incumbent upon you to represent the firm well, don’t shoot from the lip and above all, keep your emails clean, sweet and legitimate!

Chere Estrin is the CEO of Estrin Legal Staffing; CEO of the Paralegal Knowledge Institute and Co-Founding Member of the Organization of Legal Professionals. She has written 10 books on legal careers and hundreds of articles and is a popular national seminar speaker. Her blog, The Estrin Report, has been in existence since 2005. Chere can be reached at chere@estrinlegalstaffing.com.