Email Inbox Management

How I Manage My Email

(29 January 2008)

I watched the Google Talk video about the Inbox Zero concept. It is long (about 60 minutes) but the first half hour especially is good, where he talks about his system.

My system is similar. I don't process to zero (ie reduce everything to an empty inbox every time) the way he does, but I do take similar steps.

Everything Needs A Place

Every inbound email needs to be put in a place. Your list of places will be different from mine, but my list of places is pretty short:

To-do (longer term): At work we have a web site that holds our customer requests. The vast majority of emails should either be held in that system as an open ticket, or the fresh information appended to an existing ticket. Once that's done, the email can be deleted.

To-do (immediate): If there's a five-minute task which isn't worthy of being tracked in the to-do system, but I'm not in a place to actually do that at the moment, the email representing that task stays in my inbox.

Now the Inbox Zero guy talks about having another folder where you store this stuff, but I find that if it isn't in my inbox I don't see it, and if I don't see it I will forget it and it will not get done. This means I am "that guy" who scrolls up and down his inbox looking for things to do, but it is because I'm constantly looking for a way to get this stuff out of my inbox.

Archival: This is information I have to keep either for future reference or to cover my ass later (which is also a form of reference). I can be pretty limiting in what actually gets put in this category because of the way I manage my trash (see below).

Trash: There are two ways to get an email into the trash: it's junk, so it goes in the trash, or the task gets handled, so it goes in the trash (this means the task gets recorded in the to-do system or it just gets done and isn't worth tracking). Either way, it is gone.

The bottom line from these four places is that with very, very few exceptions, the place for email is not my inbox.

Make sure things get put in their place

I do my best to ensure that my email gets filtered when I look at it, but I find that things accumulate, either because I'm not paying attention (ie overnight) or I'm too busy to close the loop on things (ie playing whack-a-mole through the day).

So twice a day I go through my inbox with a more brutal filter than I normally do: first thing in the morning, and last thing in the afternoon.

The morning is easy because I get all kinds of robot summaries from the overnight activity. So I skim some of them, and delete others unread. Every report gets skimmed a couple of times a week on average, but with some of them multi-megabyte in size I would get nothing else done if I read them all top to bottom. After a while you get a feel for the "normal" level of noise from these reports and any change will trigger warnings almost subconsciously.

At the end of the day I go through and update the open tickets with the fresh information that's accumulated in my Inbox, delete the threads which were all sent to me on a FYI basis, and delete the To-Do: Immediate tasks that actually got done.

The goal is an empty inbox but that never happens; I keep it to 20 messages max, and most days I'm at 10 to 15 messages.

This sets me up for the next time I go through my inbox: anything else there is new and can be processed aggressively.

Archiving is about Finding, not Keeping

If you keep an email, you are doing so for a specific reason: because you think that at some point in the future the information in the email is going to be useful. However, the whole point of keeping it is so that you can find it later.

In the old days, this generally meant you had a whole mesh of folders where this stuff got stored here and that stuff got stored there. And if you don't have a good email search (which today means a indexer) you are probably stuck with this kind of system. The problem is that you get confused when things over-lap: is this A or is it B because it is really kinda both, or should it go in a new folder A+B? This leads to confusion when searching for things.

The modern solution is to have a program which periodically trolls through your email client and creates an index of everything it finds. Then you can ask your program for emails with specific characteristics (ie containing words, to: or from: someone specific, date range, whatever) and it will quickly find the emails corresponding to that criteria (which hopefully contains the specific information you are looking for).

There are a couple of solutions which do this. The Windows Indexer service which is a part of some combination of Vista and/or Office 2007 does this. There is a really neat plug-in for Outlook 2003 called LookOut! which does this. And I understand that there is a Google Desktop component which does this.

My choice is LookOut! mostly because that was the first one I tried.

I did try the Windows Indexer with Office 2007, but Office 2007 caused all kinds of hilarity (including, relevantly, the indexer either failing to update itself at times or taking up 100% of the computer's resources at other times) and I ended up reverting.

I have not tried the Google Desktop.

I have the program set to check for changes every 30 minutes, and rebuild from scratch every 30 days. This is probably to fight the inevitable database corruption that happens in tools of this type. The defaults were different, at 60 minutes and 7 days, but I've never had an issue with the faster update and slower rebuild settings.

I also have it set to only index my mailbox, and not search "My Documents" or anything like that. File management is a different problem and when I'm searching for emails, that's really all I want to find.

The only real gripe I had with LookOut! is that it wouldn't index my imap account when I had it connected through Outlook. Of course since then all my imap mail is done on Google, so there's no need for this functionality.

Keep the archive simple

Today, I have basically four active folders in my email client: Inbox, Trash, Sent Mail, and Not Inbox. All of my archival stuff goes into Not Inbox because with modern tools like Lookout! for Outlook, or the Google search engine for Gmail, I can find emails that I need no matter where they are. So since it no longer matters where the emails are, I no longer worry about putting them someplace.

This is also relevant to the Trash-vs-Archiving discussion I hinted at above. My habit at work is to delete practically everything because my Trash folder doesn't automatically empty. On the first of every month I open my Trash folder and sort by date. Outlook provides me with the messages grouped by date: Yesterday, Last Week, Two Weeks Ago, etc, Last Month, and Older. So I know that everything in Older is more than a month old. So I select everything in Older, and permanently delete it.

I also keep practically everything I ever send. Right now I have more than 14000 messages in my work Sent Mail folder. And this is because we do the reply-then-quote-the-whole-damn-thread-back system at work. But the side effect is that any email I send as part of a conversation includes the whole conversation to that point. So since I've got the conversation saved in my Sent Mail folder, there's zero point in duplicating that information everywhere.

The only exception to this rule is large attachments I have sent. Every so often I go in and delete anything that's 500K or more since the attachment is probably duplicated elsewhere.

Anything which might be required for longer term goes into Not Inbox in an unsorted, haphazard way. I used to have a hierarchy of folders, but now even that hierarchy is under Not Inbox.

This all works as a system because Lookout! indexes everything, no matter where it is. So if I need to refer to something a co-worker sent as part of a conversation I was a part of, I've got it. If I need something which has been sent to me within the next month (on average an email sent to me stays with me for a month and a half) I've got it. The vast majority of stuff I need to refer to I will do so within that month, after which point it's gone.

For my Gmail account, my practice is different. I save pretty much everything in the Archived folder so that the Google search engine can find it for me if I need it. And since Google provides over six gigs of space at the moment, really why delete anything? I can always clean up later in vast swaths should it become necessary.

Any system is worthless if it hinders more than it helps

This is a lesson I learned from my days as a configuration management tool manager. In the case of a CM situation, my rule is always:

• If a tool gets in the engineers way, they won't use it.

You have to have a tool which makes it easy, trivial even, for the engineer to do the "right thing" -- whatever the "right thing" is. Otherwise they will actively subvert your system and your tools and you won't get the results you want.

This is directly applicable to managing email.

• If it isn't easy, you won't do it. If it doesn't work, you won't do it. And if you don't do it, it won't help.

I don't like Outlook, but I have to use it for work. Lookout! makes it bearable, and I understand that the Windows Search in Office 2007 is similar (I had some problems with the indexer when I tried Office 2007 prior to my reversion to Office 2003, a reversion which was driven exclusively for my desire for Lookout!'s ability to accurately find what I was looking for).

In my case, Lookout! is the one tool that makes this system work, together with the discipline to make sure that things get filed where they need to go.