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Original Essays

The Great Connector

by David Shipley
Let me begin with a digression.

It's impossible for me to write for Powell's the Web Site without thinking about Powell's the physical place. I was born in Portland (1963) and grew up there. Powell's was a fixture of my childhood, almost as much as the zoo train or Seaside or Henry Thiele's. The store was smaller, colder, dingier, moldier. The windows — and this could be memory talking — seemed perpetually steamed up. I can't help thinking back to those days now — back to those afternoons when my mom carted my brother and sister and me (all of us crowded in the wayback of her deep green 1972 Volvo, long before seatbelts were mandatory) downtown to hang out at Powell's and get lost in and among books.

Portland was so different then; it was like we were growing up on an island, cut off in certain ways from the rest of the country. (Did the forest keep everyone out? Or was it just Tom McCall?) It's understandable, I guess. For most of my childhood, Portland had five TV stations. The New York Times — not that I was particularly aware of it — was available primarily through Rich's tobacco store, and it came a few days late. We dressed the way we dressed, immune or late to Eastern or Californian trends. (There was no Gap, no Banana Republic to keep us all in a universal-American style.) We weren't immediately, relentlessly and perpetually connected to the country. For me, the joy surrounding the '76-'77 Blazers was twofold — they were an amazing team, sure, but they also got us noticed. They actually made CBS and Brent Musburger come to town. (This is before local volcanoes started erupting!) I remember going to one of the playoff games and, afterward, finding a sheet with a mimeographed list of CBS camera cues on the floor of the Memorial Coliseum, and treasuring it; it was a gift from the glamorous broadcasters who dropped in on us from the outside world.

And now? And now Portland is more a part of everywhere else than it's ever been. (And vice-versa: lots of other places have caught up to Portland or been influenced by the styles and decisions that have emanated along the shores of the Willamette.) We're all hooked up, linked, connected in a multitude of ways.

This isn't a particularly new observation, but it does bring me to the reason I was asked to write something for Powell's: One of the great connectors, perhaps the greatest connector, is email. And email is the subject of a book my co-author, Will Schwalbe, and I wrote. The book is called Send and it's a guide to emailing.

Why did we write it? Because in a very short period of time this fantastic technology that does so many wonderful things sort of arrived on our doorstep and took over our lives, and we never really had much opportunity to figure out how to use it, how to do it well and, just as important, when not to use it. This amazing, democratic form of communication — the reason, in fact, that my parents in Portland can stay connected to my children in New York — comes with a bunch of built-in traps that we somehow delude ourselves into forgetting about. And then we make really embarrassing, time-wasting, infuriating mistakes. What we try to do in the book is point out these traps and give people strategies for remembering and avoiding them.

In our book, we write, of course, about those really sexy email problems — things like reply-all disasters. And it's true — these yield some of the funniest, saddest, most compelling email tales. But they're also the least enlightening because they'll always happen. They're like walking into a door or dropping your radio into the bathtub or being hit in the nose by a rake you've stepped on. Stupid. Unavoidable. Be careful next time.

We write, too, about really dumb things people do on email — like, say, criminal acts. That said, we presume our readers are decent, law-abiding people who are not into insider trading or fraud, etc. (Just in case, though, there is a section of the book that provides helpful advice for how to stay out of jail.)

The bulk of the book is devoted to less obvious questions, but ones that have greater applicability to most of us. We were looking for insight into every day screw-ups — emails that are too formal or too casual, too angry or too sarcastic, too vague, or just unnecessary. The sins we most often commit, and which are most often committed against us.

Why, for instance, do people forget that email is a permanent medium? How did Michael Brown of FEMA, or the folks at the Justice Department who were overseeing the U.S. Attorney dismissals, or that couple at Wal-Mart who got fired for an electronic romance, delude themselves into thinking that they were not writing for the ages?

Or why do flame wars erupt?

Or why do we neglect to insert tone in our emails?

Or why do we continue to fail to pay attention to things like the To line, the CC line, the Subject line? (Probably because they're built in and we stop noticing them. And then we get into trouble.)

Actually, let me talk about the Subject Line for a second, just to make the point. Two years ago, I did not give the Subject Line a second thought. I was happy to let the Re, Re, Re's accumulate; I was happy not to update the Subject Line. This was misguided. Here's why:

Here are some of the actual Subject Lines Will and I received during a week when we were working on the Subject Line section of the book.

  • What to Do?
  • ??????
  • RE: FYI
  • Two Things
  • Great News
  • Urgent
  • Tomorrow
  • Status
  • How Is This?
  • Quick Question
  • We Would Like Your Assistance
These were neither effective nor useful. In some cases, they left us peeved because we had to take time to figure out what the email was about and where to rank it in order of inbox importance; in other cases, we just read right over them. Not one of them advanced the cause of the person who sent them.

Now, here are a few other subject lines. These worked. They caught our attention and told us what to expect. They aren't clever and couldn't have taken any longer to compose than the clueless lines we just read:

  • Comments on the Strat Plan
  • Tom and Andy's Itinerary
  • Flap Copy Due Tomorrow
  • Mom's Birthday Gift
  • Expenses Approved
A Subject Line doesn't just help the person to whom you're sending an email — it helps you, too. A Subject Line is how you tell yourself what you are saying. If you are having trouble coming up with your subject line, it's a pretty good indication that something's wrong with your message.

Of course, a Subject Line can be of great use to your recipient, as well.

To this end, here are some things to keep in mind:

  • Subject Lines need to be updated over the course of an email correspondence, both to give people an accurate picture of what to expect, and to make them notice your message, but also for important legal reasons.

    Before you send a new reply, make sure the Subject Line matches your message and tells the recipient if this email differs from all that came before it.

    This is particularly important when a thread veers off radically from where it started.

    For example, say the Subject Line says, "Time for Your Denture Sanding," and the body of the email reads, "Animal House or One Flew Over the Cuckoo's Nest?"

    This email might have worked better had the subject line been changed to the new topic, "Movie Rental for Tonight."

  • Subject lines no longer need to read: Re, Re, Re. These Re's were useful in the early days of email when it was harder to re-sort your inbox and you needed to figure out how far along in the conversation you were. Now those proliferating Re's just look like a tic.
  • Also, Subject lines should live up to their billing. Great news should be Great!!! Otherwise it can be deflating.

    Even more deflating is the message that directly contradicts its enthusiastic subject line.

    This is a real email that came to Will from his HR department. The subject line — in capital letters and with six exclamation marks — read: "MEMORIAL DAY WEEKEND HOLIDAY!!!"

    It came the Thursday before Memorial Day weekend. Very exciting.

    But the email itself read:

    "The Friday Before Memorial Day weekend is a full working day. If you leave early, you need to mark it as a vacation day."


Oh, and another thing about subject lines... Well, maybe that's enough for now. When I get going, I tend to get carried away. Will and I have become, um, fairly passionate about the whole subject of email. But there's a reason for that. Many people think, "What does it matter; it's just an email." But email is as important as anything you want to do on email. If you don't get what you want because you didn't put enough care into how you asked for it — well, that can be a huge problem.

Sometimes the huge problem, though, comes from people using email to communicate things that just shouldn't be communicated on email. Issues that are deeply emotional. Anger. Condolences. Apologies. Email is so present, so easy to use, that we use it when we shouldn't. We get lulled into eye-for-an-eye communication — a message comes to us on email and so we respond via email. This is not always a good idea. There are times when we need to remind ourselves to go off-line, to make a phone call or write a letter or walk down the hall (if that's possible).

The book, I hope, will help people remind themselves when and how best to do this. I mean, now that we're connected we might as well make the most of it — we might as well communicate in a way that doesn't drive us apart. It's strange, but Will and I have discovered that if we send better emails, we get better ones in return.

What have we learned from our digital odyssey?

To think before you send.

And to send email you'd like to receive. spacer

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