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ClearContext to deal with E-mail

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I've been meaning to write this for a while, and reading John's post on Microsoft's Email Culture finally motivated me to do so. I'm particularly interested in talking about how I deal with "Ignore Incoming Email" since that can be a major distraction.

It's been almost a year since I started using Getting Things Done. Overall I would say it's been a resounding success. I feel in control of my life, my work, my email, and my endless list of things that I want to do. However, I have had a few glitches along the way. Fundamentally, the "system" does not scale to the mail volume I receive. If I spent a minute per mail per day I would do nothing but email. Furthermore, for a few months I was spending 10 - 4 in meetings. That meant that my only time to take care of e-mail was from 8 - 10, or during meetings (which is useless), or at night. It wasn't a happy thing.

Now, some of this was a bit ridiculous. You can't be in meetings all day and expect to do any work. And if you are burying your head in your laptop during the meeting, there is no point in being there. But, beyond that, GTD does not teach you how to deal with 200-400 pieces of mail a day. I believe that the system is really suited for some one who gets a low to modest amount of mail, which does not really exist at Microsoft.

For a few months I used a system whereby Outlook would color messages where I was the only recipient in blue, if I was in the TO line in green, and if I was in the CC line in Brown. Based on color I could sort of figure out what to read first and what to leave for later. However, this was flawed for a few reasons. Out of the box, the two views that Outlook gives you that are most useful are:

  • Group by Conversation
  • Group by Date

However, both of these "sort" orders do not give you the most important information at the top of the inbox. Group by Date assumes that the newest messages are those you should read. Group by Conversation assumes that the conversation with the most recent reply is on top. These messages "above the fold" basically have no intrinsic importance associated with them.

The Inbox is really something I use for "triaging" messages. For any given messages I do the following:

  1. See if I can determine from the subject or From if I should read it immediately
  2. See if I can act on it in < 2 min and delete it
  3. See if I need to turn this into a Task ala GTD.

Now for an example. Say I get an email sent to my entire division at Microsoft, or I unnecessarily get added to a thread that I really don't need to be on just because I'm a member of some team distribution list. Well no matter how much I delete, any one who replies gets that thread bubbled above the fold. Clearly this doesn't work. I could go on with numerous examples, but at the end of the day the problem still stands. Outlook has no way of organizing the inbox in such a manner that the important stuff is above the fold. Or does it?

Over the holidays I got an email from Deva Hazarika, the CEO of ClearContext (blog), asking if I would check out his software. I was traveling at the time, but when I returned I decided to give it a go. I was very intrigued and found out that Deva actually lives around the corner from me, so we met for lunch and had a great 2 hour talk about his company, the software, and my problems with email! Since then I've been using ClearContext to see if it would work for me. As of now (1 month with the software) I cannot live without it.

First and foremost, ClearContext is a well written Outlook Add-in. I have spent my fair share writing Add-ins for Outlook, and I can smell a rotten Add-in a mile away. ClearContext has a great installer, seamless integration, and worked without any hitches. One installed ClearContext will re-arrange your inbox so that the important items are at the top. I will explain a bit how this works, but the bottom line is that it has saved me countless hours in the past month and integrated wonderfully with my existing Getting Things Done system.

ClearContext works by evaluating a number of aspects of an email to determine it's priority:

  • Who the message is from (you can rate specific contacts importance to you)
  • Which domain the message is from (for example, @microsoft.com can be higher than others)
  • Importance of the determined priority of the message
  • If you are a participant in a thread
  • The "directness" of the message

Based on these factors it will assign a "score" to a message, and a thread. Based on these scores it will sort your messages. Additionally messages are colored with Red being most important, then Blue, Green, Black and Grey (in order of priority). You can also tweak the importance of the weight of these items. For example, I made Thread Participation most important since I usually want to keep on top of thread that I have replied to.

ClearContext also has a notion of a "Topic". You can assign a Topic to a message, and then you can use a button to File that message automatically to a folder. Since I already had a folder hierarchy of Projects from GTD, I was able to point ClearContext at this folder hierarchy and it created all the Topics for me. Filing messages is a breeze now. Topic = Project in GTD.

To illustrate how this can be useful, I'll use two examples.

1) General News type message

Every day I get a few emails about "Top News Stories". I don't need to read these when I get them and if I don't get them it's no big deal. I told ClearContext that these messages are the lowest priority. As such the messages never appear at the top of my inbox, but the very bottom. I can get to them when I have time, and if I don't I just bulk delete them.

2) Threads I don't need or want

Say I get a thread that I don't need to keep on top of. Well i just set the priority to Very Low. As new items come in, they automatically go to the bottom of the inbox, and I can quickly review or delete them and they never distract me.

The basic value proposition that ClearContext offers me, also mentioned in John's post, is that as new messages enter my inbox, I do not see them at the top. If the message is not at the top, it's not important. At first I was nervous about this, but after a month I fully trust the system to do the right thing for me. It's incredibly valuable to keep my distractions to a minimum during the day, and ClearContext allows me to do that. I only focus on messages at the top of my inbox, and I never move down till I deal with those. It's instilled the rigour I need to follow the GTD Triage process.

Now, I have a few small problems with ClearContext, and I've sent them the feedback.

  1. ClearContext doesn't work to well if you have two versions of Outlook 2003 Running simultaneously in cached mode. For most Microsoft employees this can be a problem. The solution though is to run ClearContext on one machine. You still get the views on the other machine, so you don't lose the benefit
  2. You can't view messages in the Group By view. That is, messages are sorted in a flat list like Outlook XP. This is because of how ClearContext sorts items. This isn't a huge loss, but I would like to be able to also Group By Date and Conversation after applying the ClearContext sort order.

A final note. Software like this really shows the power of the Extensibility model in Outlook. I am amazed by how rich some of the add-ins for Outlook are, like Tablet Enhancements for Outlook, ClearContext, and Plaxo. Outlook truly is a platform, and one receiving a lot of attention from some really innovative developers.

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