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Sending E-Mail. Etiquette lessons from Send: Why People Email so Badly and How to Do It Better by David Shipley and Will Schwalbe. Why do we e-mail so badly?. 1. E-mail is new Letter writing has thousands of years of etiquette and expectation behind it:

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sending e mail

Sending E-Mail

Etiquette lessons from

Send: Why People Email so Badly and How to Do It Better

by David Shipley and Will Schwalbe

why do we e mail so badly
Why do we e-mail so badly?

1. E-mail is new

Letter writing has thousands of years of etiquette and expectation behind it:

What kind of paper do you use for a business letter?

When would it be all right to use pink ink?

What would you think if a wedding invitation arrived via postcard?

why do we e mail so badly3
Why do we e-mail so badly?

2. E-mail is fast

  • We must get our messages right countless times a day (the average for a white-collar worker is 140).
  • Because it’s instant, we don’t give it much thought
  • So, we often aren’t quite ourselves, and by the time we figure this out, we’ve hit the send key
why do we e mail so badly4
Why do we e-mail so badly?

3. E-mail puts us in a state of disinhibition

In face-to face interaction, the brain reads a continual cascade of emotional signs and social cues, instantaneously using them to guide our next move so that the encounter goes well…this face-to face guidance system inhibits impulses for actions that would upset the other person or otherwise throw the interaction off.

Daniel Goleman, The New York Times

thus the 8 deadly sins of e mail
Thus, the 8 deadly sins of e-mail
  • Vagueness (“Remember that thing…”)
  • Culpability (“Tell them I asked you to sell the thing when it hit $70”)
  • Cowardice (“Here’s the thing: you’re being let go”)
  • Obsequiousness (Re: Re: Re: Re: Re: that thing)
  • Sarcasm (“Smooth move on that thing. Really smooth”)
  • Familiarity (“Hiya! Any word on that admissions thing?”)
  • Inappropriateness (“Want to come to my hotel room and discuss that thing?”)
just because it s there
Just because it’s there…
  • E-mail encourages unnecessary exchanges

So, if you wouldn’t stop by a colleague’s office every ten minutes for a chat, you probably don’t want to e-mail him or her frivolously thirty times a day.

…doesn’t mean we have to use it!

just because it s there7
Just because it’s there…

2. Email has largely replaced the phone call, but not every phone call should be replaced.

So, when conveying an emotion, handling a delicate situation, testing the waters, it is better to use your voice.

…doesn’t mean we have to use it!

just because it s there8
Just because it’s there…

3. E-mail means you can reach everyone, but everyone can also reach you!

So, when you write your outgoing messages, don’t assume instant familiarity. For your incoming messages you could try filters, but they are imprecise. Better to be careful about with whom you share your address.

…doesn’t mean we have to use it!

just because it s there9
Just because it’s there…

4. E-mail defies time zones; it can also defy propriety!

So, don’t forget that every e-mail is an interruption. If the matter isn’t urgent, a letter can be less intrusive.

…doesn’t mean we have to use it!

just because it s there10
Just because it’s there…

5. E-mail provides a searchable record; therefore, you can be held accountable for what you’ve written AND received!

So, choose your words carefully and watch the e-mails you get. Careful record keeping could be essential.

…doesn’t mean we have to use it!

just because it s there11
Just because it’s there…

6. E-mail is way too easy to forward.

So, never forward anything without permission, and assume everything you write will be forwarded.

…doesn’t mean we have to use it!

just because it s there12
Just because it’s there…

7. E-mail allows others to change your words.

So, if you need to send a sensitive document via e-mail, one where your words must not be changed, use .pdf or another hard-to-alter format.

…doesn’t mean we have to use it!

just because it s there13
Just because it’s there…

8. E-mails not only come with baggage—they are baggage!

So, before you send an e-mail with a ton of attachments, keep in mind the following: pack carefully and travel light.

…doesn’t mean we have to use it!

just because it s there doesn t mean we have to use it so what are the alternatives
Just because it’s there… …doesn’t mean we have to use it!So what are the alternatives?
  • The Letter
  • The Fax
  • The Phone
  • The Text or Instant Message
  • The Face-to-face
  • Silence
anatomy of an e mail
Anatomy of an e-mail
  • To
  • Cc
  • Bcc
  • From
  • Subject Line
  • Attachments
  • Flags
  • Font size & color
  • Openings and sign-offs

Try to avoid directing your e-mails poorly

1. don’t send it to too many people

2. To and Cc are not created equal

3. be careful about revealing others’ addresses

4. use the best possible address

5. watch the order you list recipients in

6. Beware the accidental To

(autofill & send buttons are often culprits)

  • Picking sides
  • Dropping/adding as you go
  • Escalation
  • Going Public
  • Writing to CEOs
  • Reading incoming Ccs
  • Reply or Reply All?
  • Big Foot and the Flattering Bcc
  • Inside vs. Outside
  • Informing without escalating
  • Tells your recipient where the message is coming from and where his reply should go.
  • Be careful with the addresses you use. is not appropriate for business.
Subject Lines

Here are some real ones received in one day:

What to do?



Two things

Great news



“ “


How is this?

Quick question

We would like your assistance

Subject Lines
  • If you’re having trouble with the subject line, the problem may lie with your message
  • Always use them, but not as your entire message!
  • Make sure they reflect your first item and the entire content
  • Use specific, identifiable names
  • Update the subject line when you reply…don’t Re: to infinity
  • Don’t exaggerate
  • Make sure they’re necessary
  • They take up valuable space, carry viruses and often trigger junk mail filters
  • Tell your recipient it’s there and what’s in it.
  • Make sure you name the file clearly
Font size and color
  • The medium should never overwhelm the message
  • It should be readable (12 point san serif is best for computer screens)
  • Not all computers will be able to translate your font and color
  • No background or wallpaper, please
  • Cold calls call for titles
  • Be extremely careful with mail merges
  • Use honorifics where appropriate
  • Dear is perfectly correct
  • Use full name if there is gender uncertainty (or do some research)
  • Groups call for some creativity, but “Greetings” will do just fine
  • Who are you?
  • Make the jump to first names cautiously
  • Salutation-free e-mails only when there is an ongoing conversation between colleagues who are peers
  • Closings: should be appropriately formal (best, sincerely, cordially)
  • Signings: Sign the way you would like to be addressed
  • Signature Blocks: Make them plain text, nothing fancy, with pertinent contact information
  • Mirror the actions of your correspondent unless he or she is being too informal
types of e mail
Types of e-mail
  • The Ask
  • The Answer
  • The FYI
  • The Thank-you
  • The Apology
  • The Connection
The Ask

Make sure what you are asking for is reasonable and unavoidable. If so,

  • Consider whom you are asking
  • Use more than e-mail
  • Make your request at the top
  • Mention connections early
  • Stay focused
  • Be brief, but not too brief
  • Make the request stand out
  • Start small
  • Be up-front
  • Help out
  • Be polite
  • Follow up gently
  • Allow a graceful out
an effective request
An Effective Request

Dear Mom,

Today was the day of our phone call. I did not like the way it went. I am very mad at you. I want to come home after visiting day. I know a lot of kids go to four-week camp, and will be home by the time visiting day comes. So I will not be bored at home. Even if no one was back, I would be happy and excited going with you to your office every day. I am happy as long as I am with you. I will make a deal with you: If I really, really still hate camp by visiting day, then I get to go home, but I have to try to have fun. Does that sound like a fair deal to you? It does to me.


The Answer
  • Answer at the top, not the bottom, of an email.
  • If you’re interlacing your response in the original email, make sure you differentiate the font somehow.
  • Make sure your date and time stamps are accurate.
The Answer
  • Be honest about your intentions
  • Be fast, but sensitive, with bad news
  • Stand back and see what others do
  • Know when to stop responding
  • Apologize when you’re late
  • Respond quickly to maintain relationships, offer condolences, or ease anxiety
  • Use the out-of-office assistant creatively
  • Use the sent e-mail as a guide
  • Let the receiver know you don’t expect a response
  • An FYI often does the trick
  • Also make it clear if the person is free to forward the information or not.
The Thank You
  • Keep it to scale
  • Hit your target
  • Don’t mix your message
  • Thank even small favors, but don’t go nuts!
The Apology
  • Is e-mail the best way to apologize?
  • E-mail is a great way to start an apology
  • Put the word “sorry” or “apologies” in the subject line
  • Absolutely ask permission before you Cc on an apology
writing the apology
Writing the Apology
  • Use active voice
  • Take responsibility
  • Stay away from qualifications
  • Propose a plan of action to fix the damage
  • Keep it short
if an e mail got you in trouble
If an e-mail got you in trouble…
  • An e-mail will NOT get you out of it. Fall on your sword over the phone or in person right away.
  • Don’t blame e-mail for the mistake—you wrote it!
  • Pray that the wounded party has made a similar mistake and is willing to forgive.
The Connection

Remember the pleasantries: ask after health, family, whatever is appropriate

Remember to occasionally send the “how are you doing” e-mail.

how to write the perfect e mail
How to write the perfect e-mail
  • We are deluded by the “e” in e-mail:
    • we tend to think of it as an ephemeral, temporary thing
    • we tend to view letters as more permanent, but you can burn a letter!
  • E-mail is storable AND searchable, so compose it with care.
choosing the right words
Choosing the right words

English relies heavily on nuanced tone to convey respect—not easy in an e-mail.

Be vivid and specific without forgetting what your original relationship is with the person to whom you’re writing.

Also, don’t forget context: is this a serious subject? Are you e-mailing the person at work? Are you just saying hello? Do you want a favor? And what is your particular company’s culture?

choosing the right words40
Choosing the right words

Note the difference between the words in these 2 e-mails, both written by a 12-year-old girl named Ming:

Hey, Annie,

That was MEAN of your mom to say that you’re fat! You are SO not fat! And stuff like crunches and junk! I’d totally DIE! I HATE exercising. But OMG! You saw a really cute boy!! That rocks!! The only REALLY cute boy I’ve seen in ages is James, but he is so cute I don’t care. Hee hee!! Maybe you’ll get to see him again, and u can ask him out r somethin. And don’t worry :) u’ll see some cuties soon, i bet. oh g2g!

L8ter ;)


Hi Daddy!

How are you? I’m doing well, but I miss you a lot! The weather here is all rainy and cold and it’s very boring. It’s probably nice and sunny in LA. Grrr, I’m jealous. I’m thinking of writing another “My Place” story. You know, the kind that’s all descriptive. Do you have any ideas about what I can write about? I miss you a lot!! I love you!!



choosing the right words41
Choosing the right words
  • Don’t be too informal; if you are applying for a job, don’t be slangy (“bummer!”), familiar (“dude!”), or quirky (“right-a-roony”).
  • Also, don’t try to impress using words you don’t understand (“Considering this is a very contemporaneous issue, I am resubmitting it to you for consideration at this time.”)
for instance
For instance

Five Words That Many People Misuse:

  • Disinterested (impartial and objective)
  • Irregardless (doesn’t exist; use “regardless”)
  • Literally (does not mean figuratively)
  • Nonplussed (means confused, not nonchalant)
  • Penultimate (second to last, not really great)

This will get you in two ways:

  • It will be read as sloppiness and failure to proofread (writing “sned” instead of “send”)
  • It will be read as ignorance, or a lack of knowledge about the proper use of a word (writing “affect” instead of “effect”)

It’s often acceptable to be lax about grammar, punctuation, capitalization and spelling in an e-mail

That does NOT mean it is always acceptable to be lax about these things!

When should we be sticklers?

When can we relax?


More importantly, grammar can convey TONE.

  • Simple sentences intensify: depending upon your relationship with the receiver, they may seem direct and unvarnished or childish and dictatorial.
  • Complex sentences soften: these can seem conventional and elegant or blathering and pompous.
please thank you and other insulting terms
Please, Thank You and Other Insulting Terms
  • Please is a slippery word (“Would you please remember to include me on the email whenever you respond to a customer?”)
  • Thank you should NEVER be used before a favor has been done (“Thank you for making sure I get the report”)

Laxness is only okay when you are on familiar terms with the person you are writing to.

Never forget that punctuation affects meaning:

  • Let’s eat, Mommy. vs. Let’s eat Mommy.
  • No, thanks to you. vs. No thanks to you.

Keep them short, or they won’t get read.

Don’t bury your main point.

Break a paragraph when you shift topics.


Common contractions should be the default

The uncontracted form is for special emphasis



Never, ever capitalize a pejorative word

Only use them if you are supremely happy about something or are otherwise conveying joy and good wishes

Otherwise, capitalize normally…I don’t care if it takes longer!

Emoticons (-:

These are great for quick e-mails between friends:

1. They are a convenient shorthand

2. They can clarify irony or convey warmth

However, do not use them if:

1. You are writing a formal email

2. You’re trying to compensate for a barb, a risky joke, or sarcasm


Same goes for exclamation points!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

And Abbreviations


the truth
The Truth

The most well-constructed e-mail is at a disadvantage if it’s dishonest

1. Be yourself

2. The hallmark of phoniness is excess (researchers at Cornell have shown that when people lie while instant messaging, they use more words than they do when telling the truth)


When to think twice before hitting the send key

You are very emotional (especially angry).

Sarcasm and loaded rhetorical questions are famous for starting flame wars.

Watch out for gossip and duplicity.

Bottom line: if you wouldn’t say it to someone’s face, don’t put it in an e-mail.

When litigation comes to town
  • Avoid even appearing dishonest or illegal
  • Watch phrasing, even as a joke
  • Be careful what you keep (follow company policy)
  • Be careful what you share and pass on
  • A sudden flurry of deletions can look incriminating
Don’t let e-mail take over your life
  • Re-sort your Inbox for a fresh perspective
  • Hold the Bacn
  • Pretend it’s a game
  • Tackle it bit by bit
and finally
And Finally…

The E-mail Golden Rule:

Think before you send.

Send email you would like to receive.