Continuing the discussion from this article…

Okay, you’ve blocked out time to handle email. Now what?

You need a plan.

I’ve tried a bunch of different workflows for handling my inbox. I’ve ended up with a very simple one, but it works pretty well for me. Your mileage probably varies, but consider using this as a template and adapt it as you feel makes sense for your situation.

I use my inbox as my “to do” list. Anything in the inbox needs some kind of attention. When I’m done with it, it leaves the inbox, never to return.

I’ve tried using a lot of task-specific folders, I’ve tried using many filing systems. I’ve kept a “todo” folder. I’ve used no folders at all. I’ve ended up with a folder structure that looks like this:

• Inbox
• Archives
• Mailing Lists

Seriously. that’s it. Sometimes I will create a folder for some ongoing task where I want to cloister all of that email together, but then I treat that folder as its own inbox and manage it like one. But typically, I may only have one or two of those, for the duration of the project.

The only thing I use mail filters for today is to automatically sweep mailing lists into the mailing list folder. That stuff is by definition bulk mail; it can wait, so I don’t want it clogging up my inbox.  Many times people are on too many mailing lists, and they try to force their way through them. As I talked about when talked about RSS in On Filters and Echo Chambers, if you can’t get through this stuff consistently without stressing yourself out, start unsubscribing. It’ll be obvious which mailing lists to get rid of because they’re the ones you’re leaving from day to day, or deleting messages unread to keep up. Save yourself the hassle and stress, and just turn them off. Or if they’re something you can’t (an external mailing list that won’t unsubscribe, or a work list someone thinks you have to read that’s pure noise), filter them to the trash. Trust me, I haven’t yet worked at a company where I wasn’t on at least one mailing list by fiat that nobody ever noticed if I just made them all magically disappear.

If you aren’t sure how to filter mailing lists, “full headers” in your mail client is your friend. Most mailing list systems put some headers in the email that are hidden by your client, but which can be used to identify the mailing list explicitly so you get no false positives and no misses. List-ID is a good one to look for. (for the geeky, that’s RFC-2919); many mailing lists also support list-unsubscribe (RFC-2369) and I do wish it’d become more endemic and mail clients had fully adopted some of the capabilities it was intended to allow (and yeah, if you look, you’ll see my name tied up in some of the arguments about those headers…).

So mailing lists are hidden in a folder and waiting for you to have some free time to browse through them. (I’m assuming you keep a work inbox and a personal inbox. If you don’t, you’re crazy, and please set it up right away. And make sure the appropriate emails go to each; so when you’re busy at work, you can ignore personal stuff, and when you’re at home, you can choose to turn off work. If you mix them together, you probably will never get your inbox straight).

I keep email sorted by date received, newest emails at the top. So at a glance, I’m looking at the most recent, unread ones. When I go into my inbox, the first thing I do is check each unread email, one at a time. My goal is to resolve each email on first reading — which isn’t always possible. but that’s the goal. This first pass is triage.

You read the email. Does it need a reply? No? Great. So either delete it or archive it. I delete stuff I know I don’t care about (like Jira update notices) and archive everything else. It’s not 100%, but 90% of the time, I trash auto-generated emails, and I keep almost everything else. It all goes in that one big archive folder (but more on that later).

If the email does need a reply, then if you can reply immediately and can reply quickly, do it. My rule of thumb is 2-3 minutes or less, reply and file. Longer than that, reply if I have the time, otherwise defer. Again, the goal is to get it out of your inbox, and if possible only have to read the damned email once. Any email you reply to you keep, so reply and then stuff in the archive folder. And it’s gone.

I have my mailer set up to cc myself on replies, so I always have a copy of what I wrote. Those all go in the archive, too. This gets all of that stuff out of the way — but I can refer back to it through looking into the archive or my computer’s searching tool (like Spotlight).

So, any time you look at the inbox, anything unread needs triage. Anything read has a pending action (by you or waiting for someone or something to happen). By the time you triage all your unread mail, you’ve deleted or filed most of it, and you’ve answered a large chunk of it and you’ve gotten a huge chunk of that email out of your life forever (or at least in someone else’s inbox to be frustrated over).

Here’s a special case: if there’s an email thread going on where you have multiple emails on the same thing, that’s a good time to switch your client to sort by subject so they all group together. Read them all together, then decide if a reply is needed to the thread. You save yourself (and others) the joy of you answering an email someone else already answered and duplicating the answer — and adding to the sag in everyone’s inbox. Many times, you’ll find someone else handled it, and you can read and file instead of continuing or lengthening the thread, or you can reply only to a specific subset of items and keep it shorter and simpler. And pull a half dozen emails out of the inbox in one bunch instead of plowing through them interspersed with unrelated emails. it’s a judgement call, but once you realize you can reconfigure your client on the fly to resort your inbox, you can learn to take advantage of that. Another sort I use a lot is by sender, so I can see everything a specific person (or mail daemon) is sending me. that can be useful to grab a bunch of things, send a single reply, and file them in bulk.

Some people use a mail filter to color certain sender emails a special color so they stand out (hint: your boss’s emails!). I don’t. My goal is to handle everyone’s emails in a timely and efficient manner so I don’t have to handle my bosses email as special cases. I think doing that sets up a mental workflow that works to the detriment of actually processing the inbox well — but it’s an option to consider for some situations (and people)

If you’ve thought about this workflow,I am recommending that you handle your inbox primarily LIFO (last in first out). That is both a blessing and a curse. It’s a blessing, because the LIFO method puts the newest emails at hand to start, and those are the ones you are most likely to be able to process and file — and in the triage phase, your goal is to get as many emails out of the inbox as efficiently as you can — while answering appropriately and good writing and appropriate content. It’s really easy to empty the email with shoddy replies and faux answers, but that doesn’t help solve the real problem, which is getting things done (another reason why “inbox zero” is a bad goal. the real goal is to get stuff answered and filed).

You can’t spend 100% of your time in LIFO/triage mode, or the older stuff gets buried and lost, so once you finish triaging new emails, start working through the ones you left behind. Generally, I do that by focusing on emails from today and yesterday, but a couple of days a week, I start with the oldest and look at each one; the idea is to put your eyeballs on everything pending often enough that you don’t forget it. Some of them will get answers or become irrelevant along the way — archive them. Some of them you’ll decide you aren’t going to answer; archive them. when you’ve moved out of triage mode, use the time you’ve allocated to do what is needed to get to the point where you can answer emails, answer them, and archive them.

(digression: about now, I hear a few of you saying “but I never even get through triage!” short answer: then you aren’t allocating enough time, so you need to block off more so you can. Or, you need to find ways to reduce incoming email, and triage more emails in less time. The latter typically means responding to fewer emails and filing more unanswered. In a work situation, answering email of your coworkers is part of your job, so you have to make sure you budget time to do it appropriately. In  a personal inbox, you have more leeway to trash emails that came in from unexpected sources. Learning to give yourself permission to NOT answer emails is important, or the obligation will bury you.)

As you get used to this workflow, you’ll get into the rhythm. It’ll take some time. The large majority of emails will go from unread to archive quickly based on one viewing. a big part of the efficiency of this workflow is that most emails only get touched once, and you take an action and forget them. The intent is to minimize how many times you look at an email and try to decide what to do. A few emails will take a long time to deal with and archive; and one or two may refuse to die. Sometimes, the work to respond properly is complex enough that you’ll need to make it its own task and allocate time JUST to deal with that email.

Hey, who owns your time? You? Or your calendar? But that’s a different discussion (hint: if you don’t actively manage your time on your calendar, you’re giving everyone else carte blanche to screw you over by taking up all your time for their priorities. Learning to actively schedule your time on your work calendar is key to finding time/ability to focus and produce; if you don’t, you’re life will get eaten by meetings until everyhting is hunt and peck in the minutes around them…)

And that is how I try to keep my inbox sane. To summarize:

• Allocate time to your email; the inbox is not something that will magically empty, and you’ll never succeed doing it around the edges of your other tasks. It is its own task, treat it as one.
• Try to touch an email once. Learn to touch each email as few times as possible before resolving.
• Don’t let emails die of neglect. Review all non-archived emails weekly to see if you can move them forward or resolve them. Don’t be afraid to declare them resolved or no longer of interest and archive them.
• Archive aggressively. Get stuff out fo the inbox so you aren’t spending time looking at stuff and trying to remember if you answered them.
• Delete almost nothing; sometimes, you need to go back to an archived email for context. Or the thread returns to life. Disk is cheap. but your inbox is expensive. Love your archive folder. desktop search (or gmail search) will become your friend.
• Stuff that isn’t bringing you value, dump. unsubscribe or filter.
• Keep your filtering simple; otherwise, maintaining it becomes a task in itself and waste time you should use on doing email.

And with a little practice, you’ll be able to keep your email inbox lean and under control. Mostly.

A few words on the Archive folder:

I used to try to organize my email archives. Desktop search cured me of that. Now, I simply shove everything in a folder called “Archive”. Every week to ten days, I take everything older than two weeks, and move it into a second Archive folder that’s dated (“2011-06″). I also do that for my “sent email” folder. Then I delete all of that mail out of those folders, leaving only the most recent stuff. And then I clear my deleted email folder of anything older than a week.

That keeps any single folder from getting too large. My active email is in my inbox. My recently touched email is in Archive. My fairly recent email is in dated folders within easy reach. Email older than three months (“2011-02″) I export those folders as .mbox folders and get them out of my active email system — and then import them into a secondary mail client that makes them visible to the desktop search (in my case, I use Entourage or Outlook for work, and Gmail for personal; my .mbox files get exported and the imported into Mail.app so Spotlight can see them as needed; if I want to open an older email, spotlight will fire up mail.app for me). that removes that email from the server and the mailboxes, which speeds up dealing with the mail servers (those of you with zillions of emails in your folders and lots of emails on the other side of Exchange or Outlook, you’re slowing yourself down). I keep old email indefinitely — just not in a place where it clutters up and slows down what I’m doing.  That keeps your email trim and fast as your server will allow; but keep older email around if you need it, which you’ll find is going to be pretty rare.

Doing that folder management in the archives takes me maybe 20 minutes every couple of weeks; It’s a good investment in keeping the mail server running fast.  Guess how often I’ve talked to someone who’s told me “god, Gmail performance sucks” only to find their primary mailbox has 12,000 emails in it? And yes, sometimes gmail performance does suck, but if you do that to the server, you’re not helping your own cause.

On a typical day, my inbox has about 80 items in it waiting for me. When I’m ahead of the game, about 40. When the inbox is winning, it grows to 300 or more (and I get frustrated) — that’s when I know I have to temporarily allocate more time to email.

Multi-tasking in meetings won’t fix this. trying to squeeze it in between meetings won’t. Realizing email is something you have to dedicate chunks of time to, and learning how to use those chunks efficiently — that’s the solution here. Or at least, part of one for most people. There’s no one perfect way to handle this, every situation is going to be somewhat different. Hopefully, though, this gives you some context to look at what you’re doing and find a way to get your inbox under better control.

I thought I’d forward the discussion of email charters and intelligent agents a bit, I wanted to point to a couple of interesting follow-up pieces: Michael McCracken posted Email Charters and Lists as Parties, and calls out Luis Villa’s blog on Mailing Lists are Parties. Or they Should be. Both are well worth a read. He actually makes some very good points, and I’ve touched on some of them a bit in the past (see The Lifecycle of Mailings lists [2002], An Audience of One [2010], etiquette, “standards” and online social environments… [2004]  and just for giggles, How Many Mailing List Subscribers does it take to screw in a lightbulb [2001]).

Yes, I’ve built email systems and run mailing lists since the dark ages, so I have a few opinions on them. I think Luis has some neat ideas, best summed up here:

Bottom line: Software can’t save a mailing list full of people who actively dislike each other. Maybe I’m crazy, though, but it seems like software that helped mailing lists function more like parties could really help mailing lists cope better with anti-social people.

In which he’s effectively calling for (whether he realizes it or not) the USENET “kill file“, although the modern flavor of that are the various reputation systems that are being invented (and the one I really like and which seems to be the one people are borrowing heavily from these days are the Stack Exchange systems).

But enough linking around for now.

The ultimate failure of mailing lists — and one we never solved over 20+ years of using and innovating them — is that they don’t scale. They seriously suck at scaling. They are a push-oriented, interruptive system that ultimately controls you, and you have to fight to keep some control on it. The easiest way to make a mailing list fail is to make it popular. They don’t scale to size, and they don’t scale to volume.  I can’t tell you how many times a mailing list I ran got into a really interesting discussion and a bunch of users got going and started talking about it, only to have others on the list walk in and start yelling at everyone to shut up and quit dumping crap into their inboxes.

Imagine that, a communication service that works best when people don’t really use it. But when it gets used and gets popular, it causes problems.

So from the very beginning, understand that email bankruptcy is not you, it’s the technology.

And the key to avoiding email bankruptcy is understanding that — and that gives you hints on solutions to preventing it, or getting your inbox back under control.

I’ve been doing email for 25+ years now. Most of my email environments tended to be high volume; people suffering from email bankruptcy. Currently, email is a huge part of my job — right now, I’m sending (sending, not receiving) ~225-240 emails a day on average. My inboxes see about 400 on a typical day. My record for sending email in one work day is around 550.

So if your inbox makes you wince or cry, I feel your pain. Been there more than once. I’ve reworked my email workflow many times looking for the magic solutions. And here are some of my thoughts on how to get out of it if you’re there, and how to avoid it if you’re not.

There are two primary causes of email bankruptcy:

• Arriving email interrupting you: when you start getting too many emails, it prevents you from actually focusing on things are spending any significant time working on anything.
• There are so many emails in your inbox you never get to the bottom of it (the legendary “inbox zero” syndrome).

How do you get there? Here are a few rules and thoughts:

Inbox Zero is not the goal. Inbox Management is. So don’t stress yourself trying to get to Inbox Zero. What you want is an inbox that you can look at and know at a glance what’s going on and what needs your attention.

Complex filtering systems are not the solution — unless they are self-teaching and self-learning. Frankly, most filtering systems in most email clients just plain old suck, and they are more trouble than they are worth, except for very simple, “let’s take a broadsword to this problem” solutions.

Keep it simple: you don’t fix the problem by shifting the problem from dealing with the email to trying to maintain the workflow.

If you take nothing else from this article, take this item: in talking to people over time over getting their email under control, the single most common cause of email bankruptcy is that they are doing significant amounts of communication via email, and they have somehow convinced themselves they can do it around the edges of their real work. Email is a task, and you need to commit time to it, the way you do meetings and your other tasks.

This is an amazingly common situation; you get up, you get to work. you try to check emails on the bus or at stoplights; you run to your first meeting, in the five minutes before everyone gets there, you’re madly scanning your inbox. While in the meeting, more emails come in. You have three meetings in a row, and suddenly people are sending emails asking why you aren’t answering emails. So in your next meeting, you try to multitask and do both the meeting and email. And suddenly, you’re doing nothing well.

Sound familiar? Yeah. I do it to at times. We all do.

So the first rule of avoiding email bankruptcy is admitting that email is a task and allocating time to it. Block time in your calendar for it. It is really a virtual meeting (albeit not real time, not face to face). It’s part of your work or personal tasks, and you will fail if you treat it as a hit and run situation. How much time depends on your life, your inbox and how your inbox relates to your work or personal situation — but stop pretending you can just handle it ad hoc, and schedule it into your life.

If you do not do this, your relationship with your inbox will never stop being a guerilla warfare situation, and it will win.

So find time to sit down every day and deal with your inbox. Maybe an hour, maybe 30 minutes twice a day (morning and afternoon, whatever you find works.

A side effect of allocating a regular timeslot to your inbox is this: it gives you permission to shut email out of your life at other times. If one of your problems is you’re constantly having email interrupt your other tasks and breaking your focus, learn to turn your email off! But psychologically, people find that hard if they know at some level they’re behind and have emails that need your attention. Your guilt at not having gotten to you inbox tends to make you bounce in and out and check every incoming email for an emergency, whnich breaks your focus, which ruins your productivity and train of thought, which means other tasks take longer, which means you have less time to do email, which….

So set up your schedule so you spend time focusing on email and handling it, so you can give yourself permission to ignore it (because its not out of control any more!) and all of your work will happen better. And when you do have that five minutes before a meeting, you can use it dealing with an email or three, and not feel pressure to “catch up”, because its’ all handled. So even that mini multitasking will be more effective and less stressful. And you’ll be a lot less tempted to multitask a meeting (unless its really boring).

Okay, you’ve blocked out time to handle email. Now what?

We will cover that in the next piece. Stay tuned….

(edited to add: hmm. Looks like Matt Cutts might be interested in these articles…)