The best and most comprehensive advice on emailing comes from David Shipley and Will Schwalbe’s book, Send (Penguin Random House: New York, 2010).
I took extensive notes while reading this helpful book. I’m posting my notes here, but I encourage you to purchase and read this book on your own. It has comprehensive advice on this tricky little communication.
Chapter 1: When Should We Email?
Method of delivery sends a message of its own.
Just because we have email, we shouldn’t use it for everything.
Consider the strengths and weaknesses of each form of communication (similar to channel and medium discussion in text)
Seven Big Reasons to Love Email (p.17)
- Email is the best medium ever created for exchanging essential information (quickly).
- You can reach almost anyone on email and not just businesspeople.
- Email knows no time zones—it’s an efficient and economical way to communicate with people around the world.
- Email gives you a searchable record.
- Email allows you to craft your message—or your response—on your terms and on your own schedule.
- You have the choice of preserving and presenting parts or all of a string of preexisting emails.
- Email lets you attach and include additional information that the recipient can retrieve when and if he chooses.
Eight Reasons You May Not Want to Email (p.22)
- The ease of email encourages unnecessary exchanges.
Rule: If you wouldn’t stop by a colleague’s office every ten minutes for a chat, you probably don’t want to email him frivolously thirty times a day.
- Email has largely replace the phone call, but not every phone call should be replaced.
Rule: Conveying an emotion, handling delicate situations, testing the waters—all these are challenges better undertaken with the human voice.
- You can reach everyone, but everyone can reach you.
- Hierarchy-free fosters a lack of informality that’s often misguided; ex Hey Professor or Hiya; poll conducted by International Association of Administrative Professionals found that 43 percent of administrative assistants write and send emails under their bosses’ names, 29 percent are allowed to delete emails before their boss has seen them.
- The fact that email defies time zones also means that it can defy propriety. Don’t know if it’s worth opening until you open it; according to New York Times after a worker has been interrupted with a message, it generally takes nearly half an hour for him to return to his original task—40 percent moved on to completely new tasks leaving old task unfinished.
- The fact that email always provides a searchable record means that you can be held accountable for your electronic correspondence.
Rule: If you’re working with weasels, watch their emails like a hawk.
- The ease with which an email can be forwarded poses a danger.
Rule: Never forward anything without permission, and assume everything you write will be forwarded.
- With email, your words can be changed.
Rule: If you need to send a sensitive document via email, one where it’s essential that your words not be messed with, send your message in a pdf.
Email attachments don’t just come with baggage—they are baggage.
Rule: Before you send an email laden with attachments, keep in mind the following: pack carefully and travel light.
A Quick Word About the Handheld
Important courtesy to observe when sending an attachment to someone you suspect might be on a handheld is to provide a summary of the attachment includes and mention the urgency. Handheld checking is not all that different from any other sort of behavior that demonstrates you aren’t paying full attention to the people you’re with.
The Letter: Fully a third reported that they still sent letters and faxes every day.Letters aren’t interruptions.
The value of a letter is greater because someone had to go out of his/her way to get the envelope, stamp, etc.
A handwritten note makes it personal.
You can change your mind and not send your letter.
Six reasons to Send a Letter instead of an Email (p.37)
- Want a document that you can archive;
- Want to create something recipient can savor (commendation);
- Don’t want to interrupt someone;
- Want to present complex topics;
- You really mean business and want to register it;
- Material is confidential.
The FAX: Three Reasons to Send a Fax Instead of an Email (p.38)
- Because a fax has a signature.
- Can send important hard documents (without scanning)
- It’s more secure
The Telephone (p.39)
There’s something intimate about a phone call.
You can read the cues from the voice.
You can change course as you get feedback.
People use email for bad news because the phone takes courage.
Seven Reasons to Use the Telephone Instead of Email (p.42)
- You need to convey emotion;
- Cut through the communication forest;
- Need to move fast;
- Want communication to be private;
- Need to reach someone who doesn’t check email;
- Want to engage and respond immediately;
- Can soften the blow of a harsh blow by using the telephone as an advance warning.
Text and Instant Messages
American Idol has made text messaging more prevalent. IM depersonalizes the conversation so people pay attention to the ideas and not who said them; it preserves a record of the session
Five Reasons to IM and Text Instead of Email (p.46)
- They work in real time;
- Shorter messages;
- Self-selected working teams to talk to each other and brainstorm;
- Ideal for mobile, silent, and surreptitious communication;
- Provide a temporary record.
Ims and Text messages can be saved by individuals and company servers.
Use hybrid strategy alternating between forms.
Combitasking (doing many things at once—i.e., Iming, emailing, talking on the phone, etc.) (p.48)
But I never got that email…90 percent of messages reached their destination within five minutes, a few got stuck for nearly a month (p.49)
In person—don’t forget to show up sometimes. Never do anything electronically that you would want others to do to you in person (p.51).
Silence—never respond to spam and don’t feel obligated to respond to “personal spam.”
When a conversation is clearly over, you don’t need to reply.
There are times when nothing needs to be said (p.52).
Chapter 2: The Anatomy of an Email
TO FIELD: Not talking about mistakenly directed emails
Don’t include too many people in the To Field or no one will respond.
To is’t Cc—put the primary person in the to field and people you want to know about it in the Cc field.
Consider that email addresses are private—be careful who you share them w/
If the person has several emails make sure to send it to the appropriate one
(When it isn’t obvious ask.)
You usually can’t go wrong by replying to the address from whence
the message came—as long as you’re sticking to the same type
Never send anything to a business email address that the recipient
would be embarrassed to have the entire company read.
Fill in the To Field according to rank.
BEWARE of the accidental TO—with a slip of the finger, it’s easy to send a
message that’s half-baked or even raw (p.60). Watch the autofill portion of
your address book. Mailing lists can also be tricky.
Just because someone was in on the email exchange from the start doesn’t
mean that person should be there forever (p.63).
Unilaterally dropping or adding a Cc in an ongoing email can alter group
dynamics or create suspicion (p.64).
If you think someone should be liberated from an email chain, offer to set
that person free (p.64). The politics of the Cc—p. 71.
Escalation—if you Cc someone’s boss on a complimentary email, it’s a way
of enlarging the compliment, but the reverse holds true for a negative comment.
Going Public—Never forget that a Cc has the power to publicly shame someone. Cautionary tale of president of the China division of EMC (p.67)
Note to CEOs: make life easier and copy in the appropriate people; if you’re a
Subordinate and you are corresponding with your boss’s boss, keep your super-
Visor up to date.
Make it clear in your emails to people outside your organization why you’ve chosen people on your Cc list (p.69).
Let your recipients know in your email whether they should reply only to you
Or “Please Reply All.”
By their very nature, blind copies are sneaky things (p.74). Bcc’s should almost never be used for communication within your organization for the simple reason that you don’t want to talk behind the backs of the people with whom you work (p.74).
Bcc’s can be useful when corresponding with parties outside of your organization. Your counterpart’s boss may feel it necessary to get involved if you Cc your boss, but you still want you boss to be included—a Bcc can help you avoid this problem.
Informing Without Escalating
A Bcc to your attorney lets him know what’s going on but doesn’t bring the situation to a boil the way it would if the other side knew you were considering legal action.
The ABC’s of Cc’s and Bcc’s (and Forwarding) p. 77
If you have several email addresses and want the reply to go to all of them, put those addresses in the Cc field. Work for work emails and play to play emails—watch the addresses.
Most important and most neglect line—a subject line is how you tell yourself what you’re saying (p.80) Use two separate emails if you find your subject line has two main ideas (example w/ Will and the apology and good work) p.81.
Always use subject lines.
Requesting that someone not read the previous message, always gets them to read it.
Shorter and key words at the beginning are important—especially for the handheld (p.83).
Keep the subject line current. Update it.
Don’t fall into the “re;re;re” trap
Avoid hyperbole. Don’t mislead.
Don’t use the subject line as the message.
(Craig of Craigslist—colleague used a reference to what she had heard him say “storytelling is important.” Got a response right away—A good subject line can make all the difference.
You wouldn’t fill someone else’s closet with your stuff w/o asking, so don’t crowd his computer memory with gigantic files (p.89).
The Eleven Most Common Types of Attachments (p.89).
Urgent, Notify Sender, and Follow-up Flag (p.92)
Urgency and the desire for a response or a follow-up should be conveyed in the subject line and the text of the message itself. These options are presumptuous and they can backfire.
Font, Size and Color
In a recent survey, many employers said they would not interview a candidate if they didn’t like the font on his application or cover letter (p.95).
The medium should never overwhelm the message (p.96). Twelve-point type is the norm for business. Use black.
People you don’t know are always Mr. and Ms. Don’t start a message with Mr. Keven Bacon. There should be no double standards. Younger people writing to older people should address the person formally. If you use mail merge, get it right.
Use titles (honorifics) when appropriate. You are free to ignore all uses of Ph.D. and if you have one, don’t put it after your name in a letter.
Dear is always acceptable and always correct (p.99)
It strikes us as rude to bark out someone’s name “Del.” Similarly “Hey”, “Hi” and “Yo” should be employed with caution (p.100).
A gender-neutral name can be addressed “Dear Pat Riley.”
“Dear Colleagues” “Dear Friends” Dear Coworkers are all acceptable. “To Whom It May Concern” is not.
“Greetings” also works.
Who Are You?
A clear indication that it’s ok to move to the first-person familiar is if the person signs his or her email with a first name only.
Keep Your Distance
If someone in our overly flat (and overly familiar ) world has taken liberties with your name—just write back with full names and honorifics.
As You Were
Once you use first names, if you go back to more formal address, someone will assume you are no longer friendly (p.104).
Salutation-free: emails among colleagues that are your peers; close friends
Two parts: the word or words that precede your name, the closing, and your signature (way you present your name)
Best, All best, Best regards, Best wishes, Regards, Sincerely, Cordially, Sincerely yours, Yours, Love, Love and kisses and xxoo (last three not used in business)
Matter of style—Sincerely is the coldest, Best and Best wishes are at the moment the most common in email (and safe); just make sure not too formal or informal; instead of keeping track of what one you’ve used for whom—just choose one and stick to it or mirror the email you receive.
Signature tells people how you would like to be addressed. Initials can be maddening to a confused recipient.
Elements of a Signature Block (p.112)
From lawyers, accountants, and other handlers of sensitive information
Chapter 3: How to Write the (Perfect) Email
Because it’s often acceptable to be lax about the rules of grammar on email, there’s the misconception that its always acceptable to be lax about them. That’s not the case (p.115).
Choosing the Right Words
English relies on subtle tone and vocabulary conveys tone. The words can be formal, casual, or in between. Literal/figurative; precise/vague; understated/correct/exaggerated; simple/complex; common/rare; prosaic/or not; trick is to be vivid and specific without forgetting who your audience is: What is my relationship to the person I’m writing?
Example of Ming Lee; Don’t choose words to impress: ”There’s always an element of buffoonery when someone uses a big word incorrectly.
Five Words Almost Everyone Misuses (p.121)
Disinterested-impartial and objective NOT BORED or UNINTERESTED
Irregardless-NOT standard English; use regardless
Nonplussed-confused NOT nonchalant
Penultimate-second to last (not last or really great)
Presently-shortly or soon (not at present or now)
Vocabulary is situational.
Careful word choice is the objective, but poor spelling that reads as sloppiness or worse yet—results in an entirely different word can be more harmful; example given The Dangerous Lives of Alter Boys (supposed to be Altar).
“Grammar is as important in determining tone as word choice is. The very same words, in different combinations, may or may not mean the same thing. But even if they mean the same thing, they may or may not convey the same tone. Good writing is good writing NO MATTER THE MEDIUM” (p. 124).
Example President Kennedy to McNamara (p. 125)
Keep in mind: Simple, short, repetitive grammar intensifies; complex, clause-filled, rhythmically varied sentences generally soften the message.
Please is a slippery word. It can be used in the wrong way: “Would you please remember to include me on the email whenever you respond to a customer?”
It’s ok to be lax so long as you’re on email and on familiar terms with the person to whom you’re writing. Punctuation is a “reading tool” (p.128). Punctuate correctly for those senior to you. Watch out for trailing punctuation…What’s so bad about a period?
Any kind of relaxed punctuation IS NOT appropriate in letters or memos. (You can change the meaning if you drop a comma.) (Find the example in Eats, Shoots, and Leaves for this.)
Keep them short.
Break a paragraph when you change topic.
Don’t bury a key point in a long paragraph.
Use white space.
Without them the tone is formal and a bit stuffy. In email use contractions otherwise it will be viewed as emphasis and might add chill to the relationship.
The writer is SHOUTING. There is an implied casualness to all-lowercase communication too.
They are handy and great for shorthand; they can be cute, ironic, or tongue-in-cheek; but don’t use them in any kind of formal email or if you’re trying to make a sarcastic comment and thing the emoticon will lessen the hurt feelings.
Exclamation Points!!!!!!!!!!!!!!!!!!!!!!!!!!! (p.135)
Infuse the message with warmth, and kick it up a notch, but use them sparingly especially in a serious correspondence. Don’t use them for a negative emotion as it will be read as a tantrum.
They have an important function as they are shorthand and they can help facilitate communication and bonding. Don’t use them when the conversation is formal or the other person might not know the abbreviation.
What Every Sentence Needs: The Truth (p.138)
“Truth in writing shines through—as does falsehood and phoniness” (p.139). Hallmark of deceit is excess: too much politeness, too many big words, too much of anything means someone is trying too hard.
Good example on p. 139 posting of James Dilworth the CEO of a small company who posted on Craigslist.
Chapter 4: The Six Essential Types of Email
The Ask: A Guide to Requesting (p.141)
Email makes this way to easy. Think before you fire off a request. Be careful to read the request from the other person’s point of view. It may be intrusive and inappropriate. Tone is important
Who are you in relationship to the person you are asking? Subordinate? Superior?
More Than Email (p.144)
Use combination strategy: introduce w/ an email and follow up w/ a phone call.
From the Top (p.144)
Attention grabbing and then request (direct—AIDA)
Stay Connected (p.145)
A friend in common, someone who recommended to contact
Ask for one thing.
Be Brief (p. 145)
But Not Too Brief (p.145)
Supply the details. Be specific.
Make It Stand Out (p.146)
Don’t let it get buried in the text.
Start Small (p.146)
Make a smaller request first; example of 144 “housewives” and Stanford survey; “foot-in-the-door” strategy
Be Up-front (p.147)
“It is dispiriting to discover that what you thought was a genuine and friendly overture was in tact the pretext for a bald request” (p.147).
Help Out (p.149)
When in doubt email between nine and five, M-F. People tend to read their newest emails first, so if the last one is more abrupt than the first couple, it won’t help.
Be Polite (p.151)
A little flattery never hurts, and it’s sometimes necessary to be extravagantly polite, but don’t exaggerate.
Follow Up Gently (p.152)
Second time around, “I know how busy you are…”
Tread Lightly (p. 153)
When you have power, be careful not to request frivolously; someone might take your seriously.
A Graceful Out (p.153)
If you give someone a graceful “out” it means you have a potential “in” with them.
An Effective Request (p. 154)
Example of child who wants to come home from camp.
The Answer: A Guide to Responding (p.155)
People expect to receive a response to an email within three hours (2006 survey). One in twenty expected to receive a response w/in five minutes!
Three Absolute Rules of Responding (p.156)
- Answer at the top.
- If you interlace your responses between paragraphs, make it obvious.
- Make sure your date and time stamps are correct or it could end up in a weird location in someone’s inbox.
Be Fast with Bad News (p.157)
Don’t make someone sit around wondering,
But Not Too Fast (p.158)
Make the respondent know that you thought about it. And don’t send bad news late on Friday.
Stand Back (p. 158)
IF you’re one of many responding, you might hold back and be able to see what’s already been covered and write “I agree.”
Sometimes the Most Eloquent Email is No Email at All (p.159)
No response is called for if someone continues to send an offensive communication. If you are so angry you can’t respond w/o losing your cool, it may be better not to respond at all.
Other times When You Care Enough to Stop (p.159)
Opposite of a nonresponse is the overresponse—“So here’s the rule: it’s fine to continue confirming and responding as long as there’s a realistic chance of misunderstanding. You can even go one step past tha, signaling the end of the email string with a “Done” (p.159).
When You’re Really Late (p.159)
It’s better to send a late reply than on reply at all.
Five ways to apologize for an inexcusably tardy email (p.161)
- I have the awful feeling that I’ve neglected to answer your kind email
- I woke up in a panic with the realization that I neglected to answer you
- A thousand apologies for the slowness of my reply
- I am a horrible person and a terrible friend
- I have no good excuse for my rudeness in not answering
Making Up (p.161)
If you’ve irritated someone at work that you like and admire, be quick to respond to every email. Reply promptly and with special cheerfulness to people with whom you’ve had misunderstandings.
Relieving Anxiety (p.162)
It’s a good idea to respond to someone quickly who is experiencing anxiety.
You can send an email and follow up with a letter or phone call.
Treat them as you would regular ones: respond quickly.
Out-of-Office Assistant (p.163)
This is a courtesy that helps alert people that you haven’t responded not because of rudeness, but because of absence.
The Last Re-Sort (p.163)
Resort your inbox if you’re feeling overwhelmed.
Suggestions from Lawrence Lessing if one becomes bogged down in email sea (p.164).
Respond in kind: a long chatty email= a long chatty email; a fragmentary email with a fragmentary email; be sensitive to whether or not the sender labored over his/her response; also depends on corporate culture
The Facts: A (Short) Guide to Informing (p.166)
Share information and let the receiver know no response is necessary. FYI does this as well as “Please don’t reply.”
Gratitude: A Guide to Thanking (p.167)
Keeping It to Scale (p. 167)
Make the thank-you proportional to the original deed.
Hit Your Target (p.167)
Make sure you thank the right people. If one did more than another, don’t group them together. It does more harm.
Mixed Messages (p.168)
Don’t ask for something and thank them. They don’t mix.
A Favor Is Still a Favor (p.168)
If someone forwards your something, makes an introduction, or emails you requested information, answer with a thank you.
Stop the Madness (p.169)
But don’t go overboard. A simple thank you is good.
Groveling: A Guide to Apologies (p.170)
An apology must be sincere. Usually it requires a face-to-face groveling.
Use the active voice if you must email: I made a mistake is better than Mistakes were made. I’m sorry I hurt you is better than I’m sorry you feel hurt. Keep it short. It’s not about you.
Four Thoughts About Apologizing on Email (p. 171)
- Don’t hide behind the technology.
- Use the email to start an apology put carry it forward.
- Put the word “Sorry” in the subject line.
- Don’t Cc without permission.
The Email Oops (p.172)
If you fired off a thoughtless email, don’t apologize with another email.
The Three Cardinal Rules You Absolutely Have to Follow If you Are Trying to Apologize for a Mistake You Made on Email (p.173)
- Email got you in trouble, but it won’t get you out.
- Don’t blame email.
- Pray the wounded person has made a similar error and is willing to forgive.
Social Glue: A Guide to Connecting (p.173)
Effective emails are clear, concise, and friendly. The movie recommendation, the jolly message that comes out of nowhere can be social glue, and can be the most important emails.
Chapter 5: The Emotional Email (p.175)
Beasts of email: anger, sarcasm, and duplicity
Write them in a word document and then decide later if you really want to send it.
Expressing anger might cause more unrest. Make sure it’s worth it.
Deborah Tannen’s List of Six Ways Women and Men Tend to Use Email Differently (p.185)
- Flame wars; men use aggressive language and think it’s funny-women are more likely to feel attacked.
- Women expect a pleasantry in the beginning.
- Women want empathy, not advice; men want to fix the problem.
- Men are more likely to send jokes.
- Men tease more often; women might get insulted.
- Men think an email apology is sufficient; women generally don’t.
“Of all the tonal choices you can make in correspondence, the decision to use sarcasm should be carefully considered, and almost always abandoned (p.186).
Study presented indicates that sarcasm only understood 84% of the time (p.188). And if it is understood it won’t endear you to the person. If you have to use it, do it in person.
Loaded Phrases and Rhetorical Questions (p.190)
I can’t imagine why
You’ll have to
Is it too much to ask
Why in the world
It seems odd that
Just curious, but
Please explain to me
Example of Ann (p.91)
“As a general rule, if a question can’t be answered without a loss of face, or if you already know the answer and don’t like it, or if you don’t know the answer but don’t care, then it’s not a question; it’s there purely for tone” (p.193).
Don’t encourage gossip or duplicity with emails.
A Few Words on Being Mean (p.195)
Don’t do it in emails. Example ketchup story.
How to Stay Out of Trouble (p.198)
“If you wouldn’t make the comment to the other person’s face and stick around for the response, you probably shouldn’t put it in an email” (p.198).
Chapter 6: The Email That Can Land You in Jail (p.199)
Cataphora helps lawyers analyze millions of emails. It looks for “worried” language—phrases such as “can’t sleep,” “high blood pressure,” “confused” etc. It looks for changes in style and traffic patterns. Advice: Be consistent in how you write your emails, whom you include, and when you send them (p.202).
Email is easily made public and can live forever. William Morris Agency in LA in 1992 six employees were fired for remarks about executives of their firm.
Enron, Arthur Andersen, WorldCom, Merck, etc.
Insider trading tips, fraudulent schemes, maps showing where the bodies are buried, but there are even more traps that are less obvious…
The Email That Appears Criminal but Isn’t (p.201)
The Email that Asks Questions That Can Come Back to Haunt You (p.203)
Even the innocent, well-intentioned question on email can become part of a permanent record. Example the “$5,000 email.” Advice: There are certain constructions to watch out for if you’re writing on a potentially sensitive matter. If you find yourself emailing, ‘Do you REALLY think it’s a good idea to…?’ be aware that it’s implicit that you think it isn’t. Phrasing your concern as a question won’t get you off the hook later on (p.204)
Most companies are actively monitoring employee emails. 36 percent of employers use software to track content, keystrokes, and time spent at the keyboard; 38% have people whose job it is to monitor your email. Don’t put anything in a personal email sent from a company computer that you wouldn’t want the HR department to read (p.207.
The Email That’s Not So Funny (p.207)
People send inappropriate (racist, sexist, pornographic) jokes. In April 2006, the U.S. Mint in Denver paid its female employees ~$9 million partly because of raunchy emails. Advice: If you’re looking for a list of what not to joke about on email, look no further than the nondiscrimination policy of your company or organization (p.209.)
The Email That Shouldn’t Have Been Shared (p.210)
Three examples on page 210.
Advice: Loose lips sink ships—and so can sharing and forwarding.
The Email You Should or Shouldn’t Have Kept (p.213)
Tips for archiving: Keep the same stuff; discard the same stuff. People get in trouble when they deviate.
How to Delete Something So It Stays Deleted (p. 215)
Good analogy: “Once you decide to delete, it’s like taking the garbage from your kitchen and putting it in your hallway. It’s still there.” You have to use a secure delete or a rewriting program to make sure it’s not elsewhere. And if you’re on a system with corporate backup, that probably won’t work.
When in Doubt (p.216)
Eliot Spitzer, New York’s governor when he was state attorney general: “Never talk when you can nod. And never write when you can talk. My only addendum is never put it in an email.”
Chapter 7: S.E.N.D. (p.217)
This is an easy, four-question checklist—to help you determine whether you should or should not hit the Send key.
S stands for simple.
E stands for effective.
N stands for necessary.
D stands for done. (“Am I moving things forward, or am I just moving them off my desktop?”)
The Last Word (p.220)
“Let’s all cut one another some slack….But let’s not cut too much slack, especially when it comes to our own behavior.”
Think before you send.
Send email you would like to receive.