A Crash Course in Organizing Your Email

One of the unavoidable features of modern professional life is a never-ending stream of email. Over the years I have come up with a few tricks that really help me stay at email nirvana: “inbox zero.” People around here tease me about it, but I have a very tidy inbox. I thought I would share some techniques (tricks) I have found useful. Like most companies, my employer uses Outlook/Exchange. I also use Gmail for personal and professional email, especially when I’m mobile.

Before Gmail, email vendors had standardized on a trio of email organization schemes: folders, flags and filters. Outlook, Notes, and others provide a similar triumvirate.

1. Folders: A person files email into a hierarchical folder tree. Each email can sit in one folder. Each folder sits in another folder.
2. Flags: A person (or a filter) can flag emails for attention. Outlook provides different colored flags, to which the person may assign their own semantic meaning. Flags have three states: off, on and completed.
3. Filters: Incoming emails are automatically managed using a preset routine. For example, a filter can file emails matching certain criteria into a specific folder. All incoming email from listservs is filed into a folder called Lists.

If you look at most people’s work email (which I consider a professional research technique rather than an invasion of privacy, per se) you will see an explosion of folders stretching for several screen lengths. You’ll see folders within folders and folders with date ranges associated with them. This is one of the keenest examples of personal information architecture, and to me often one of the saddest.

I mention that these three organization schemes dominated prior to the arrival of Gmail because Google transformed two of the three established email organization schemes and turned the entire paradigm on its head. Google arrived in a relatively stable search market and created a revolution; in my opinion they have done the same for email. Gmail offers three organization schemes, just like Outlook - but the way they work is quite different. The first major change is Gmail’s most granular organization tools act on threads instead of messages. There is very little a person can do to a lone message - almost all actions work on the entire thread. Most people get this right away and like it. The second major change people will notice is Gmail doesn’t support folders - Gmail just doesn’t have them. That stopped a lot of people cold. Here is what they offer instead:

1. Labels: Labels are assigned to email messages, like tags. You can tag the same message with several labels, such as work and to-do and project_x. I’m not going to debate the Clay Shirky-ness of tags vs. folders, but I assume if you are reading my blog you get it. Looking at their inbox, a person can quickly see the messages and the categories at the same time. That’s super useful, but I suggest a couple of label tricks below that make them even more flexible and useful.
2. Stars: Stars are simple one-click markers on email messages. Stars have two states - on and off - so stars act like flags. But unlike a traditional email applications’ flags, Gmail provides a special view of all the starred messages.
3. Filters: Like traditional email programs, Gmail provides filters that run automated routines on incoming messages. Google actually didn’t do much radical here. However, since a person can use filters to leverage the other two schemes, they take on special new power. For example, multiple filters can act on the same message, applying different labels simultaneously.

That’s enough background. Let’s get on with the tricks!

Gmail Tricks

The Archive and the Inbox. I’ve got 65,000 messages in my archive and 22 messages in my inbox right now. I have zero unread messages. Any message I am definitely going to need in the near term stays in the inbox. I use stars and labels to put more information on the messages, but basically only current messages survive in the inbox and everything else goes right into the archive. This means I always have fewer than 25 messages in my inbox - a single page of email. Conveniently, Gmail returns the entire thread to the inbox if there is a new message, so I don’t have to worry about losing context when reading a new message from an archived thread.

Labels act like folders. Each label has its own folder view, which shows all the messages with that label, acting like a non-exclusive folder for those messages. Since the labels are semantic (they have real meaning for the person who created them), they provide a more flexible alternative to folders. I have filters that apply a label to all my work email, all my listserv email, all my recurring receipts, and messages from friends (see image, on right). Anything that doesn’t filter into a label either deserves special attention or is immediately archived. I create temporary labels for projects or tasks. For example, while looking at job descriptions for RIA designers recently, I applied the label positionDescription to the useful search results from my archives. Later, I can treat those results like a convenient folder for analysis.

Labels act like flags. Each folder can be assigned a different color and has its own semantic meaning. The colored labels show up on the messages in the inbox, acting like little colored flags. Labels only have two states - on and off - sacrificing the completed state of traditional flags. You won’t miss it, since you can use stars to show completion (see the next item).

Stars act like a to-do list. There are a number of ways to use stars, but I use them as a to-do list. Any message with a star is active and requires action on my part. There is a special view for all Starred messages, showing them reverse chronologically. When I complete the action specified in the message, I uncheck star and the message disappears into archived anonymity.

It’s Google, so you can search. One of the strongest features of Gmail is that search actually works. If you’ve tried to search for a message in Outlook, you know what I’m talking about. I admit that searching for a keyword is not much of a trick. The trick is that Gmail uses search to generate all its views, like labels, stars and archive - so you can hack it for your own nefarious purposes. Here is one I use all the time: search for l:unread to display all the unread messages anywhere in your account (inbox or archive). I occasionally archive listserv emails without reading them. This let’s me identify those messages even if they get buried in the archive.

Outlook Tricks

Flags are better than folders. I use flags to mark the status of a message. I do not use folders (at all!). Instead, I mimic Google’s setup with only two folders: inbox and archive. There are six flag colors in Outlook, and I have assigned a meaning to each:

• red:action required by me
• blue: important, but no action
• purple: awaiting action by someone else
• orange: kudos from customers and coworkers, saved for reviews and proposals
• yellow: urls and account information
• green: bill codes and project funding

Smart folders are really smart. To their credit, Microsoft added smart folders to Outlook recently, and these mimic the functionality of labels to some degree. But they are a poor substitute, lacking the ability to add semantics to traditional flags. However, you have to work with the tools you are given.

• Active. I have set up a smart folder to display all the flagged and unread messages in my account. I call this one Active, since it contains everything I’m still working on. I occasionally flag my own sent messages (usually blue and yellow) and the smart folder picks those up too. This smart folder needs to be viewed chronologically, since it’s also an archive back forever.
• Critical. I created a second smart folder of red-flagged messages called Critical, since it contains just my own current action items.

These are the only two ‘folders’ I ever use. Anything that earns a flag is archived in the corporate email system. Anything that doesn’t earn a flag is purged after two months. I generally have five to fifteen critical messages requiring immediate action, which is what I consider my ‘inbox’ - quite a manageable list.

update! An astute reader asked if you could union two labels into a query. You can! Put this in the Gmail search box: label:name1 label:name2

update! A good post over at Jounce about deleting and archiving email.

another update! You can see people celebrating inbox zero here.

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A Rant About Application Customization

Okay, new rule! If I select the same preference customization when an application starts ten consecutive times, that application must remember and execute that customization permanently. If not, I get ten dollars from the manufacturer for every subsequent failure. It should remember it on the first try. But ten! Ten is insulting. I think this is a fair rule. You ignore my wishes ten times, you give me ten bucks. It’s more than fair, and it should be part of the ULA. I’m looking at you, Microsoft.

Toolbars.

I set up the toolbars in Visio to my liking. Like all the apps in MS Office, Visio has a customize function that gives me the sense that the designers wanted me to customize, that they felt it was something I should be able to do. I like this feature and use it extensively. Ah, but providing the interface and then not following through with actual customization is basically cruel. Every time I launch Visio, it loads the Reviewer toolbar. I don’t want to see it. I don’t use it. It also loads the LiveMeeting toolbar, which I neither want nor use. And yet here they are, every single time. So, I hide them every time I launch the application, which is about ten times per day.

Within the span of a single day, Visio could learn what I wanted by observing these simple repeated behaviors. It already tracks the usage of individual icons and menu items, hiding them if they fail to see much usage. That’s the exact same kind of observation and customization I want. But instead it ignores the clear explicit signals, like whole toolbars that I clearly never ever want to see again and explicitly ask to be hidden every single time the app launches.

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NBC Pulls Out of iTunes Deal

I apparently missed this news back in December. I have been re-watching seasons 1-3 of Battlestar Galactica in anticipation of the fourth and final season. I went to iTunes to sign up for the season pass of downloads… and it’s gone. Apparently NBC wanted $4.99 per episode and Apple said no. In fact, Apple said more than no, cutting NBC off prior to the start of the Fall season rather than waiting for the contract to end in December. Charging $4.99 per episode works out to $100 per season of BSG. Who would pay that? That’s criminal! The six-disc DVD is $45 and the HD-DVD is $100. NBC thinks we will pay inflated HD prices for regular low-fi content? Seriously?

Sadly, I was ramping up to cut off our cable service this month. But with Heroes, BSG, the Office and other favorites permanently off iTunes, it will be a little harder for me to pull this off. We will be relying heavily on Netflix, but then we must wait until the end of the season to start watching.

Also on the horizon is Xbox Live, which is building up a fairly substantial digital media library of their own. Serving up affordable hi-def digital content on a device that is already plugged into my TV is a pretty compelling business model. Their TV collection is quite limited for now, but it keeps growing every time I check back. As I have said before, Xbox Live is the future of Microsoft.

Here’s an update (4/7/2008):

NBC apparently has licensed BSG through Amazon’s Unbox service. That is great news if you are a PC user, but people on Macs are SOL - there’s no Mac version of their rights management software.

Interestingly, the Amazon price is $1.89 per episode - $0.10 cheaper than the original price on iTunes. Does that mean NBC is loosing money? Or is Amazon loosing money? Or is Amazon realizing some cost savings somehow? Regardless, it’s a far cry from the greedy $4.99 NBC wanted from Apple. Take this as a valuable lesson, NBC - don’t kill the golden goose.

another update (6/2/2008):

Fancast also offers free episodes of BSG, and their player is Flash-based so it works on Mac (and it looks decent full-screen). Yay! The only downside is that they are a couple weeks behind. I guess that’s a small price to pay to keep free content free.

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On Tagging (from the archive)

I taught a class on tagging for Vera Rhoads at the University of Maryland Graduate School back in 2006. It was an introductory-level presentation, aimed at covering the basics. Last year, I presented a similar presentation on classification, tagging and search.

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Search Presentation (from the archive)

I have given versions of this information retrieval talk for five or six semesters at Thom Haller’s USDA Graduate School class on Information Architecture. I always enjoy the class, since Thom attracts folks with an interesting range of experience.

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