As I mentioned in yesterday’s blog posting, several of the Web 2.0 companies I visited last week told me, in no uncertain terms, that they believe that email is “broken” — with the implication that their company’s products and services would repair the damage, and make us all happy, productive people once again.

I’ve been doing a lot of thinking about email for the past several days; I’ve also been googling the Internet and blogosphere to see what other people are thinking and writing about email. I don’t claim to have all the answers, but since email is one of the most heavily-used tools in the day-to-day life of most computer-equipped knowledge workers today, I think it’s important to start a dialogue on the subject.

The reason(s) we might argue that email is broken fall into one or more of several categories:

1. Email actually works fine, but it’s been hijacked by the Forces of Evil.
2. We never learned how to use the capabiilties of email, and our behavior is akin to driving a car on the freeway at 60 mph in first gear.
3. There are some straightforward things we’d like to accomplish in email, but the most commonly used email products don’t support them adequately.
4. We’re misusing email, attempting to make it serve purposes for which it wasn’t intended (and for which the Web 2.0 vendors have alternative solutions)
5. The way my generation thought about email when it was introduced in the 1960s (the era of rotary phones, 33 RPM phonograph records, etc.) is not the way my children’s generation — or their children’s generation — think about email as we move further into this decade of the Noughts (or Zeros, or Zips, or whatever we’re calling this decade).

Let’s take a quick look at each of these…

Email has been hijacked by the Forces of Evil

I had forgotten this assertion until I began googling the search phrase “email is broken” yesterday; lo and behold, there were articles and blog postings with exactly that title back in 2003 (see, for example, this article in Salon magazine and blog postings here and here). The problem, according to these articles, was spam, which was beginning to clog our email inboxes; there were estimates that 40-70% of all email traffic consisted of spam, and dire predictions that it would represent 98% within another few years. Pundits wrote books on the topic (see, for example, Danny Goodman’s Spam Wars: Our Last Best Chance to Defeat Spammers, Scammers & Hackers), legislators passed laws, law-enforcement officials hunted down the “spam kings,” and software companies rushed to provide a variety of spam-blocking tools.

Well, spam is still a problem, but it obviously hasn’t overwhelmed us completely. Some of us get our email from ISPs that do a reasonably good job of server-side spam filtering; some of us subscribe to “trusted sender” email mechanisms that only allow email messages to pass through their gateway if they’re on a “white list” of known friends and colleagues. Many of us have email programs with a sophisticated “adaptive” mechanism for detecting junk/spam mail (my Apple mail program is reasonably good in this area.) And some of us have invested a fair amount of energy in creating our own spam filters within the email program; over the last three years, for example, I’ve added two thousand separate spam filters to my mail program, in addition to the “generic” filtering that the mail program does on its own.

We still have a long way to go before spam is completely under control, but I think the gloom-and-doom warnings from 2003 are no longer a major worry.

We never learned how to use the capabilities of our email programs

If you tried to drive your car at 60 mph on the freeway in first gear, chances are that the engine would overheat, grind to a halt, or malfunction in some fashion within a short period of time. You might then express outrage that the auto manufacturer’s product had “failed,” but experienced drivers know that cars weren’t meant to be driven that way. I often have the same feeling when watching my friends and colleagues interacting with their email program.

For example, I’m amazed by the number of people who have no email folders; everything is in their inbox — including read, unread, relevant, irrelevant, current, and obsolete messages. Yes, I know that most email programs provide a means of sorting, filtering, and searching through a collection of email messages — but a lot of people haven’t figured out how to use those capabilities either.

And sometimes the ignorance is a little more subtle; it’s not that people can’t use their email program at all, but that they’re unaware that a few simple tricks would make it much more useful. For example, scanning through a long list of messages in one’s inbox to get a sense of which ones have arrived from family members, important clients, or other classes of recipients, one can either use the tedious left-brain approach of looking at the sender’s name, or the right-brain approach of color-coding the message titles, with the use of some simple email filtering rules. In my case, any email message from a family member is color-coded a dark blue; mail from personal friends is color-coded light blue; messages from clients are dark pink, prospective clients get a light pink, business colleagues are brown, and messages with “urgent” in the subject are color-coded red. As a result, the list of messages in my inbox looks like a rainbow, but I can instantaneously tell who’s trying to get my attention.

On a more mundane level, there’s a never-ending stream of recommendations and guidelines for using email more effectively — e.g., set aside a specific chunk of time at the beginning or ending of each work-day to process email, rather than allowing oneself to be interrupted every time a new message arrives. I typed the search phrase “using email effectively” into Google, and got 92,700,000 hits. Presumably not all of them are relevant(!), but this and this and this are a small sampling of common-sense recommendations that could help eliminate the “email is broken!” complaint from a lot of people.

There are straightforward things we’d like to do, but our email programs don’t support them

As mentioned above, some ISP’s have email services with server-side spam filtering. But not all of them do, including Apple’s .Mac service. Not only does this waste bandwidth, by transmitting spam (sometimes with attachments) to my desktop/laptop computer before its gets eliminated, but it’s even more of a nuisance if I forward a copy of email to my Blackberry or my cell-phone’s email service (both of which are associated with T-Mobile).

Another example: Apple’s Mail program has a nifty command called “Bounce”; as the program’s on-line help window says, “When you bounce a message, it appears to the sender that your address is invalid. This is useful for rejecting mass mailings from companies whose mailing lists you’ve been added to after buying products from them.” Unfortunately, you can’t specify “bounce” as a specified action in an email “rule” or “filter,” which means you have to “bounce” all messages manually. Grrr!

Most of us who have taken the time to explore all of the capabilities of our email programs probably have a list of such omissions, weaknesses, or downright bugs. They’re not “strategic” failures, and they won’t prevent us from using email; but they persist, year after year, and they make us wonder whether we’ve reached the limit of what we’ll ever be able to do with email technology.

We’re attempting to use email for things it was never intended to do

This is what most of the Web 2.0 vendors are focusing on: their point is that we use email for a wide variety of activities and interactions, some of which would be better served by blogs, Web-based calendaring systems, or other such tools. And they argue that in order to “process” or respond to a typical business-oriented email message, we have to “break context” and switch our attention to some other program that provides critical information — e.g., a map, a purchase order, a calendar, a spreadsheet — when we should be taking advantage of Web 2.0 “mashup” capabilities to incorporate all of those activities within the context of the email program (or the blog, or the group calendaring system).

One of the most interesting insights about this issue came from an August 10, 2006 Wall Street Journal article by Jeff Zaslow, entitled “Hoarders vs. Deleters: How You Handle Your Email Inbox Says a Lot About You.” Mr. Zaslow says that “The makeup and tidiness of your inbox is a reflection of your habits, your mental health and, yes, even the way Mom and Dad raised you.” He recommends emptying your email inbox hourly, observing that, “”You have to treat your inbox like you treat your mailbox at home. You wouldn’t store your bills inside your mailbox. And leaving spam in your inbox is like leaving garbage in your kitchen.”

On the one hand, this is common sense; but for me, it was a real eye-opener. I deal with my email fairly promptly and efficiently, but I’ve always noticed that by the end of a busy work-week, there’s a “residue” of several dozen emails in my in-box that I’ve read, and perhaps forwarded to someone else, but nevertheless haven’t fully disposed of. All of these unresolved emails represent tasks that need to be done, but which haven’t been entered on my “official” to-do list, and therefore haven’t really been identified as such — and haven’t been scheduled as to when they’ll get done. After reading Zaslow’s article, I’ve now changed my behavior: I don’t empty my inbox every hour, but I do make a point of emptying it at the beginning of each morning, so that all of my to-do items are collected in one place.

What’s important about this is the recognition that the email inbox has become a form of to-do list, and that the activity of sending and receiving emails is that of creating and accepting tasks. Indeed, a substantial amount of the email traffic within a typical office environment is workflow-oriented: sending a to-do item to one’s co-worker or subordinate; acknowledging the receipt of a to-do item; following up to find out why the to-do item hasn’t been done; notifying one’s boss or co-worker that the task has been done; seeking approval from one’s boss in order to take the actions required to carry out the task; granting such authority to one’s subordinate; and so on. Arguably, these workflow-related messages should be removed from the rest of one’s email traffic, and managed separately; yes, I know that Lotus Notes has a workflow capability, but most straightforward email programs don’t. Meanwhile, several of the Web 2.0 vendors will be happy to show you the workflow capabilities they’ve built into their zippy new blogging tools.

If workflow-related messages account for some of our email traffic, what other kinds of messages do we typically send and receive? This is probably not a complete list, but here are a few of the ones I could readily identify (Ian Delaney has a similar list on a recent posting of his TwoPointTouch blog:

• “Here’s some information that you need in order to carry out the task that I assigned to you in that previous email.”
• “Here’s a notification of the date and time of our conference call, along with the call-in number and password.”
• “Here’s something I could have communicated in person or via telephone, but I didn’t want to interrupt you. And besides, even the most trivial conversation with you takes 15 minutes, and I’m too busy for chit-chat.”
• “Here’s a message that someone sent me, and that I thought you should see, too — either because I think it’s interesting, or because I don’t know what to do with it, or I’m trying to subtly delegate the responsibility for the task to you. But I haven’t really figured out exactly why I’m forwarding it to you, so you’ll have to figure it out yourself, or waste additional time asking me what you’re supposed to do with it.”
• “Here’s a cc copy of a message I sent to Joe. I have no idea if it’s relevant to you, but I figured it wouldn’t hurt if I cluttered up your inbox with stuff like this.”
• “Here’s a cc copy of a message that’s being sent to 73 other people in the office, and it’s the 19th such message in a ‘thread’ about some topic. I may or may not have remembered to cc you on the 18 previous messages in the thread; if I did, they’re probably floating around somewhere in your inbox. I deleted all my previous messages, so don’t ask me for help.”
• “Here’s an interesting URL/PDF/newsletter that I think is funny/timely/inspiring/relevant. I know you’re in the middle of doing something else right now, but I’m not going to tell you whether you should look at this URL instantly, later today, sometime this week, or whenever you have nothing better to do.”
• “Here’s the most amazing YouTube mashup you’ve ever seen. Oh, but I forgot to tell you that it’s R-rated, and when you click on it, it’s so loud that everyone in the office will hear it.”
• “Here are a dozen pictures of my kid’s birthday party. He’s an ugly little bugger, isn’t he?”
• “Are you available for a meeting next week? No? How about the week after? Is Charlie available? Can we get a conference room? What’s the agenda? Will the necessary documents be distributed in advance?”

The first two items on this list are appropriate in almost all cases, and the third item actually demonstrates one of the advantages of email over alternative forms of communication. But the rest of the list is certainly illustrative of email misuse, if not a demonstration that email is “broken.”

Today’s generation of Internet/Web surfers has a different attitude than their parents toward email

My wife and I began emailing each other in 1968, when we worked at different branch offices of a time-sharing service bureau; we’ve emailed on a fairly continuous basis since then. Since January 1, 2000 I’ve received 16,119 messages from her (that’s only 6.6 messages per day, so it’s not as overwhelming as it sounds). So whatever communication protocols, nuances, and habits we’ve developed are pretty deeply ingrained by now.

Similarly, most of my friends, peers, and business colleagues have been using email on a regular basis for 10, 20, or 30 years. And while we all learned, early on, not to communicate EMAIL MESSAGES IN CAPITAL LETTERS, some of the other misuses of emails listed above are not just unconscious, they’re part of a deeply ingrained generational culture. It wouldn’t occur to us to complain that email is broken, because it’s just part of the technological infrastructure we’ve gotten used to — like television, automobiles, and telephones.

But there are one or two younger generations (depending on where you want to draw the boundaries) who have already created an alternative set of cultural behaviors for communication. Instant messaging (IM) was probably the first visible form of that culture, and the Web 2.0 vendors are noisily reminding us that “social network” sites like MySpace, Friendster, Flickr, and YouTube are newer and richer aspects of that young culture. I don’t need to belabor this point, other than to remind the members of my own generation that we shouldn’t be surprised if the younger generation seriously considers email as a “broken” technology when comparing it against the ones they use.

In the home environment, this probably doesn’t matter very much: if Dad communicates with his peers from the desktop PC in his den, while Junior communicates with his peers via IM on his cellphone in his bedroom, it’s just two different generations operating in parallel worlds. But in the office environment, it could be a more serious problem; after all, businesses are still hiring high-school and college-age kids, and expecting them to operate in the older-generation world of email. If young workers are forced to use communication tools they consider broken, they’re likely to get pretty grumpy. And since they’re typically so young that they don’t have a spouse, a kid, a mortgage, or a pension, they have nothing to lose if they quit; so if they become grumpy, they do quit.
And if Web 2.0 vendors start introducing alternative forms of communication (e.g., blogs and simple, free, Web-based calendaring systems) in the high-school and college environment, they may be able to send these kids from schools into small-business environments without ever having been exposed to Microsoft Outlook, Lotus Notes, Eudora, or Apple Mail.

If I were Microsoft, IBM, or Apple, I’d be worried …