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Why Email Clients Need to Change (gigaom.com)
44 points by madh on April 25, 2009 | hide | past | favorite | 33 comments


My inbox is empty, everything filed into my GTD system. I have scripts that auto-compile the financial stuff into the right place, and other scripts that semi-automate (using a Bayesian classifier) stuff that needs an answer now, stuff that needs to be answered soon, stuff I need to think about, and archive.

I hate repetition, and have scripted my most common actions. I guess I've hacked my email system.


What software do you use? Python scripts and procmail? With what GTD stuff do you interact? What do you use for archiving (indexing, searching)?


I've hooked a Python Bayesian classifier into procmail and deliver things into folders. In essence it follows the GTD input process flow and delivers emails into project, answer required (AR), archive and delete folders. The AR emails I scan and reply to every day, refiling those that have been misclassified. My weekly GTD pass checks the other folders, allowing me to reclassify when they're wrong, and deal with appropriately otherwise.

For archiving I just put it all in either a project specific repository or a single folder called "other". I can then search for keywords, but I usually pop out to a command line and grep for things if I need them.

I'm sure there's more available in existing systems, but the Bayesian classifiers also work as spam filters. I wrote them years ago and they are a great tool to have to hand.


If you have the inclination, I'm sure many people (myself included) would be interested to see your code, even if it's raw and unsupported. Cool solution.


Hmm. I'll have to think about that. There's a lot I really wouldn't release, but I'll see what I can do. Too busy just now, but I'll put it on my list.

Thanks for the interest. It never really occured to me that someone would be interested.


While that sounds fantastic, I'd venture that your plain email client is inadequate to take care of most of this. Which I think was the point of the article.


What the author's real issue appears to be here - which they don't quite articulate, but which is lurking in there - is really simple. We use email for two things nowadays: interpersonal communication and event notifications. The fact that they both end up in our inboxes is more by accident than by design, and a really good email client should probably separate the two to some degree.


It is simpler to separate the inboxes than to separate the mails.


It's not just a matter of separating the messages, though. The workflow for a notification is completely different from the workflow for a personal email (which is also quite different from the workflow for a mailing-list message).

As far as separating them, though, I suspect it really isn't that hard. Automated notifications tend to have some pretty distinctive phrases in them, and I wouldn't be surprised at all if you could get a Bayesian network to do an adequate job of separating them for you.


I have 29 of inboxes, and I have filters that categorize the mail automatically. The changes he wants are already here, and have been since the dawn of email.

The author needs to learn how to use filters.


One of my email accounts if full of activation/verification emails, forum notifications, auto reply notifications, etc.


We need two-way RSS.


Gmail has filters. Use them.

"if subject contains analytics apply label alert"

"if subject contains facebook skip the inbox"


Yeah. The authors best bet is to use filters for now. From the looks of it, he wants AI. Or an advanced Natural Language Processing. I mean going through the mails, checking them all to see if they are bills to be paid and then generate a report. Looks really cool. But too complex with what you can achieve with technology right now!


The emails from twitter, facebook and many mailing lists, have a specific format and some services(posterous) responds to a certain kinds of mails.

Thus, first step toward what Alister says, could be done by defining patterns and associate gmail filters and searches to it.

AI and NLP could have to be used sometime in the future. But for now import and export of filters should do quite a bit of it.

Literally each gmail user has to set filters for himself. Rather if it could be configured via a workflow and associated with user inbox, it would be a long way for a better email client.


Does anybody wish Gmail had an API? That would be oh-so-sweet.


GMail does have an API and it's called IMAP.

You just need to write a wrapper class to retrieve whatever info you need from the mail servers over IMAP vs a usual data API.


No, I would like to be able to write extensible plugins for the GMail web application. Or make modifications; e.g., have my starred messages be stuck to the top of my inbox. Code advanced filters and have them ping some PHP code of mine with relevant info. Make a 'dashboard'. A list of undelivered packages. etc.


It has. It is called IMAP. Joking aside, what would you want in API ? Search is something that gmail does better than most clients so that should be there


Conversations. You know, that threading-done-right they have that people love -- with a few holdouts -- but that no other email client has yet done correctly (and, no, an indented list of message titles isn't nearly the same thing, nor is IMAP THREAD's "same subject? Must be the same thread!").

There's a fair amount of deduction goes into Gmail's conversation ordering -- it's quite hard to fool -- and an API that allowed you to treat conversations as the primary unit instead of messages would be great.

This article is right that the inbox needs to get smarter, and GMail is the closest to it yet. But while they're furiously adding frills around the outside, they've made very little changes of the sort suggested. Even easy things are missing: eg, why can't I click on a "from" header and automatically see all messages sent from that person?

In fact, it's mostly small changes like this that could bring GMail much closer to what the author is looking for. Sure, being able to pull in Facebook interactions isn't going to happen, but a desktop client could certainly do that. Which brings us back to hoping for a GMail API.


Conversations. You know, that threading-done-right they have that people love -- with a few holdouts --

Oh, you mean that useless representation that breaks down as soon as a third party gets involved and that google forces upon us even in their abysmal "groups" product that everyone insists on using nowadays?

Referring to conversations as "threading done right" is the worst joke I've heard in a while. It's subset of what most e-mail clients already do with their collapsible threading based on message-id and subject and could be trivially added to same mail clients without loosing the advantages of real threading.

The reason why that hasn't happened (except in niche products) is because most people just don't consider it a worthwhile feature. It has actually done more harm than good to the e-mail ecosystem because it encourages TOFU which annoys the hell out of people using regular mail clients and completely blows up on mailing lists.

Edit: I just learned that outlook apparently has a conversation view. Well, why am I not surprised...


It's never failed me on multiple-party messages, and it's especially useful on mailing lists. What it isn't is a subset of threading. The crucial difference -- and this is why it can't be "trivially" added to mail clients -- is that it treats a conversation as a fundamental unit, not a message.

That means I see the entire back-and-forth on one page, including my replies, not a basket full of subject lines I have to click through. Even just getting my replies into a thread seems beyond most mail clients that I've seen (short of a client-killing smart basket that includes my monster sent mail folder).

Still, though, I did say there were holdouts. Hi there.


The fundamental difference -- and this is why it can't be "trivially" added to mail clients -- is that it treats a conversation as a fundamental unit, not a message.

As you've apparently never used a desktop mail client before, here's a screenshot of what the tinydns mailing list looks like for me: http://is.gd/uumd

I have no idea what you mean by "treats conversations as units". The same could be said for any threaded view I guess. Except that the threaded view also exposes the nesting, which is quite a bit more helpful on mailing lists than a flat view that jumps randomly between levels.

That means I see the entire back-and-forth on one page, including my replies, not a basket full of subject lines I have to click through.

Yes, that's nice and fancy for 1:1 conversations.

Once you participate in a mailing list you'll happily trade in the lazyness for a structured view with defined anchors that provides some clues about what point and nesting level of the conversation you're currently looking at.

Even just getting the replies into a thread seems beyond most mail clients that I've seen.

As you can see in my screenshot this works just fine. In fact it has been working fine for almost 30 years. Usenet is based on this mechanism. Did "most E-mail clients you have seen" happen to be web-based?


I refuse to make you a screenshot of gmail, so I'll just ask: what are the contents of all those messages? You don't know, because your client allows you to read a message a time. Gmail lets you read a conversation at a time. Massive difference.

[Edit since I'm now on a real keyboard]

I have no idea what you mean by "treats conversations as units". The same could be said for any threaded view I guess.

What I mean is that the atom of the mail client is an entire conversation. So when I move it to another folder (or label it in Gmail parlance) all the related messages get grouped, or flagged or whatever. You can do some operations at an individual message level so the metaphor's not overpoweringly intrusive, but for general day-to-day operation, the conversation is the unit you deal with.

Except that the threaded view also exposes the nesting, which is quite a bit more helpful on mailing lists than a flat view that jumps randomly between levels.

There's nothing about conversations that prevents this. Look at Hacker News: it has both all-posts-on-a-page and nesting. Would you prefer that the comments view was just a list of timestamps and poster names and you had to individually click each one to see the comment? No? Yet that's what most mailing list clients and archives make you do.

Yes, that's nice and fancy for 1:1 conversations.

... which are the primary use of email for millions of people. I'm not sure why you're so quick to condemn something that would be such a massive leap in usability for so many email users and that doesn't exclude your preferred method of operation.

I personally prefer to read mailing lists and usenet in thread-to-page, just as I prefer to see the contents of online comment threads and instant messages all in one screenful. You may not. But as you've said, virtually every half-decent mail client of the past 30 years can handle message-level threading.

But I want more. I actually wonder if the prevalence of mailing list-centric attitudes like yours among engineers is the reason we don't have mail clients with proper conversations yet. I actually suspect that it's still simply too hard: you have to sort and search potentially tens of thousands of messages just to display one conversation, and the easier route is just to make the human do the work. But I'd far rather my (or Google's) computer did it for me.


I refuse to make you a screenshot of gmail, so I'll just ask: what are the contents of all those messages? You don't know, because your client allows you to read a message a time. Gmail lets you read a conversation at a time. Massive difference.

I fail to see a massive difference beyond extraordinary lazyness there.

I don't normally want to see a full thread at a time. It can make sense in a web-frontend where page refreshes take annoyingly long, but other than that I see more drawbacks than benefits in my workflow.

What I mean is that the atom of the mail client is an entire conversation. So when I move it to another folder (or label it in Gmail parlance) all the related messages get grouped, or flagged or whatever.

Again, that's nice but no difference to desktop mail clients.

There's nothing about conversations that prevents this. Look at Hacker News: it has both all-posts-on-a-page and nesting. Would you prefer that the comments view was just a list of timestamps and poster names and you had to individually click each one to see the comment? No? Yet that's what most mailing list clients and archives make you do.

You said "No" where I say "Yes". I have no problem pressing a single key between reading comments. I like seeing which comments I have already read. I like seeing which comments I have replied to. I like to flag comments that I might want to come back to later. I like archieving stuff, arranging it in folders or forwarding it by e-mail. I like attachments. Yes, I love all the features that have evolved in online discussion over the last two decades and would prefer if HN was a mailing list or newsgroup.

Unfortunately that's not mass compatible because most kids these days have unlearned what a newsreader is. Hence we are stuck with the poor substitute of a web forum (and not a particularly good one, as even PG will probably admit, unknown or expired link, eh?).

I'm not sure why you're so quick to condemn something that would be such a massive leap in usability for so many email users and that doesn't exclude your preferred method of operation.

I'm condemning it because it's a step backwards not forwards and affects me, as I have to deal not only with the outlook TOFU idiots but also with the gmail TOFU idiots now. Google of all companies should know better, but "fancy" won over "sensible" one more time.

But I want more. I actually wonder if the prevalence of mailing list-centric attitudes like yours among engineers is the reason we don't have mail clients with proper conversations yet.

It's called "clue". Engineers tend to also be the most extensive users of e-mail. Most mailing lists happen between technical people. Many E-Mail Clients are under active development. If conversation views were considered a worthwhile feature then we'd be having it everywhere by now. The implementation effort is minimal.

I actually suspect that it's still simply too hard: you have to sort and search potentially tens of thousands of messages just to display one conversation, and the easier route is just to make the human do the work. But I'd far rather my (or Google's) computer did it for me.

That's nonsense. Most MUAs are already tracking "conversations" as you call them and have done so for 20 years. It's just that most haven't bothered to display the threads in a "conversation view" way, because most heavy e-mail users [that I know of] don't find that view particularly useful.


I fail to see a massive difference beyond extraordinary lazyness there.

"Laziness" is a key component of usability -- nearly all efficiency improvements can be dismissed as "just for the lazy", well back before the dawn of computers. Who needs an electronic starter for their car anyway? Surely a crank handle is fine?

I'm condemning it because it's a step backwards not forwards and affects me, as I have to deal not only with the outlook TOFU idiots but also with the gmail TOFU idiots now. Google of all companies should know better, but "fancy" won over "sensible" one more time.

It shouldn't affect you at all -- you can carry on plodding through your messages one by one in your client, and shaking your fist at TOFU from your porch recliner. But the TOFU battle is (sadly) lost, thanks to Outlook and later Gmail. Increasing client usability isn't going to affect that fight one jot.

Engineers tend to also be the most extensive users of e-mail. Most mailing lists happen between technical people. Many E-Mail Clients are under active development. If conversation views were considered a worthwhile feature then we'd be having it everywhere by now. The implementation effort is minimal.

And yet when you view a Bugzilla thread on the web, you see all the replies in a single page. I agree that if conversation views were considered a worthwhile feature by engineers we'd be seeing it everywhere by now. But this is simply proving to be another case where the use case of the vast majority of engineers is wildly different to the end-user case. Google Groups, as you pointed out above, is also incredibly popular among technical people. You can't see a reason why (though you'll doubtless have something condescending to mention about youth or branding) because you refuse to accept that it may be popular for a reason.

Most MUAs are already tracking "conversations" as you call them and have done so for 20 years.

No, no they aren't, as you'd see if you deigned to take the time to consider what a conversation actually is, an understanding you simply don't have as evidenced by your screenshot above. It's not a dumb subject-based sort, nor is simply header-based or a combination of the two. Crucially, it includes messages sent by the reader -- which is where the work is for the client: it has to sort through the entire local sent archive to render the conversation. Can you name a single client that has done this for 20 years?

Clearly, this a love-hate feature. For the haters, there is ... ooh, every mail client ever. For those who love it, there is, well, GMail. Something's amiss there, especially when adding the feature would barely impact on haters.


It shouldn't affect you at all -- you can carry on plodding through your messages one by one in your client, and shaking your fist at TOFU from your porch recliner. But the TOFU battle is (sadly) lost, thanks to Outlook and later Gmail. Increasing client usability isn't going to affect that fight one jot.

Interesting observation and no, the TOFU battle is in no way lost. It has just become a much more frequent annoyance again recently, after it had almost disappeared for a while. Thanks gmail!

Try posting TOFU to any respectable mailing list and you'll get the appropiate responses. People don't suddenly begin to tolerate idiocy only because a new broken client comes along.

No, no they aren't, as you'd see if you deigned to take the time to consider what a conversation actually is, an understanding you simply don't have as evidenced by your screenshot above. It's not a dumb subject-based sort, nor is simply header-based or a combination of the two. Crucially, it includes messages sent by the reader -- which is where the work is for the client: it has to sort through the entire local sent archive to render the conversation. Can you name a single client that has done this for 20 years?

Well, technically it's quite a trivial problem for any MUA that already has a search index - which would be most of them.

So the question would not be why couldn't they do it but rather why did nobody care to implement it, even years after gmail came along.

Maybe people who care enough to use a desktop mail client just have better ways to organize their stuff?


Maybe people who care enough to use a desktop mail client just have better ways to organize their stuff?

This is what's so perplexing about this argument, and I'm clearly not articulating what I think matters here, unless I'm just getting downmodded for my opinion. Because I care enough to use a desktop mail client, and also dislike top-posting in most cases, and am pretty anal about filing. But conversation view is a great help with all of these areas, and they're where I most keenly feel its absence.

And -- if we can set Tofu aside for a moment as a social problem -- I don't see that adding conversations would detract from the email client experience in any way. Sure GMail did it in a polarising use-it-or-leave fashion, but as an optional extra it makes a great deal of sense to me.

I mean, seriously, consider the other remotely similar forms of digital conversation we have, like instant messaging. Imagine that an IM client forced you to look in a separate place to see what you'd said, and only showed you a single post from your correspondent at once. It's ludicrous. Similarly, compare the iPhone's (or any other threaded) SMS app to the old standard of single-text-at-a-time. There's simply no comparison.

So, no, I don't think it's that "people who care" have better ways, though I strongly suspect they believe they do. Oh well. Perhaps a GMail API will come along eventually.


what do you mean by "TOFU"?



I believe GMail adds things to the header to help it track the conversation. This along with time-based subject matching allows it to handle most cases easily.


Every proper email client has done this for at least the past ten years. It's the message-id and in-reply-to headers that allow for proper message threading.


I've never seen Outlook's conversation view get things wrong.




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