SXSWi: I Can't Believe You Sent That: E-mail Disasters, Large and Small and How to Avoid Them

If you don’t know me, I both love and hate e-mail. More accurate, I used to love e-mail, now I hate it. I think it is over. It is no longer effective, particularly in business/organizations. I think there are lots of new tools to do what e-mail might have done somewhat well. Too much to write on that now. Here are the notes from a good session.

I Can’t Believe You Sent That: E-mail Disasters, Large and Small and How to Avoid Them

Will Schwalbe Random House
David Shipley Random House/New York Times
Their new book/website, Think Before You Send

It is not a technological issues, but psychological, anthropological, sociolgocial.

We are not talking about stupid people. CEOs who are insider trading on e-mail; space shuttle pilots who carry on romantic conversation on e-mail,

They showed a video interviewing people about why the love and hate e-mail. Pretty well done. All people in the video showed people who valued email and didn’t want to live without it, but no one expressed confidence in how to use it.

Dominant form of electronic business information and major player in social communication.

Last year each of the speaker received about 50,000 emails and sent about 30,000 e-mails. They were having lunch and both had had bad days. Both realized that most of what happened had happened on e-mail.

E-mails are often too vague, too long, unnatural, or unnecessary.

Email can be an enormous time waster as it creates the illusion of forward progress.

Email is dangerous because it gives us a feeling of action even when nothing is happening – Bob Geldolf

Nothing serious happens in the delay, no people dying, etc (usually).

Causes of bad e-mail, the “why’s”:
1) curse of the new – new in human history. Once we get something new, we tend to use it too much. Using it for things that should be done in person – firing, breaking up, scolding
2) If you don’t insert tone specifically, tone gets inserted for you
3) E-mail is fast, often too fast to keep up with. Volume tone, content, spelling dozens of times a day under intense pressure. Speed encourages sloppiness and that causes problems because words have meaning.
4) In face to face (voice to voice) our emotional brains are constantly evaluating the responses of the other party – email does not have that ability, but lulls us into thinking it does.
E-mail puts people into a state of disinhibition (NY Science Times).
5) E-mail actually eggs us on – more duplicitous, less aware, encourages the lesser angels of our nature – combine with an easy-to-hit send key and you have a problem
6) What works in speech and letters comes out very differently in e-mail
example: “please” – common sense says adding please to an e-mail makes it more polite. A spoken please is considerate, an e-mail please conveys a sense of exhasperation.

Video showing worst things that have happened to people using e-mail. Great anecodote about how an e-mail was sent out accidentally to 38,000 e-mail with a joke when woman was testing e-mail blast software.

8 deadly sins of e-mail:
1) unbelievably vague e-mail – “where is Dave” (which Dave? where physically? when you sent this?) – send this to multiple people and many are confused.
2) email that insults you so bad you have to get up from your desk
3) email that is cowardly. (fire people, drop bombs all while safely shielded, and emoticons that don’t soften the blow; Friday afternoon email to avoid discussing it)
4) email that puts you in jail (“Never talk when you can nod, never write when you can talk. My only addendum is never put it in an e-mail” – Elliot Spitzer)
5) the thank you e-mail – then the thank you to the thank you…
6) sarcastic e-mails – people don’t recognize this. Cornell study shows that drippingly sarcastic e-mails only read properly 87% of time. Sarcasm comes for Greek word from ripping flesh with teeth
7) e-mail that is too casual (Billie, Billster, etc)
8) inappropriate e-mail (4% of Enron e-mails were racist, sexist, homophobic or otherwise offensive)

Lesser sins:
- subject lines
- personal spam
- wallpaper

What makes good e-mail?
- love exclamation points
- like emoticons
- like furious e-mails when justified
- short paragraphs
- requests clear at the top
- top posting, not bottom posting
- simple fonts
- let people know when no response is needed
- flag-free e-mails, we’ll decide what is important
- condolences or congrats when proper follow up is coming (good for quick delievery)

Whether e-mail sticks around: the less annoying we make e-mails, the more it will continue to stay in use

Cut each other some slack, evolving too rapidly for their to be style police. But let’s not cut ourselves too much slack, let’s be careful and thoughtful

Their final points:
Think before you send
Send e-mails you want to receive

I can’t believe they didn’t list this, but my pet peeve is trying to schedule meetings, pick a dinner location, etc with 10 people over e-mail. Yikes, it never works. My new lifeline for scheduling meetings is Doodle, a website that super-easily lets you schedule meetings. Use it, you’ll thank me.

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arvind s. grover

I am a progressive educator, a podcaster (, a blogger, and dean of faculty of JK-11 school (building a high school) in New York City.