I read about ClearContext a little while ago, and it intrigued me. There’s no doubt that the concept is tantalizing; ClearContext purports to be able to arrange your inbox in order of the priority of the email coming in. In their own words, ClearContext Outlook Plug-In “automatically analyzes, organizes and color codes incoming email; presenting the inbox as it should be and saving you valuable time each and every day.” I filed the name away in my head, thinking that I’m always interested in new and different ways to make the way that I relate to my email easier and faster.

I later downloaded the trial version of their program, installed it, and gave it about a ten minute try. I’ll admit, I wasn’t fair; it changed how my inbox looked, and I wasn’t in the frame of mind to deal with that or learn a new way of interacting with my email. So I immediately uninstalled it, and forgot about it.

Then some time later I had my little fit with respect to email etiquette, which has become known as the “Filers vs. Pilers” post. While I was reviewing the comments and trackbacks on that item, I noticed a trackback that pointed to an email survey at www.clearcontext.com. When I followed the link, I found that there was no referring content - in other words, nothing that explicitly mentioned my post. Forgetting that I had heard of ClearContext before, I deleted the trackback. (I could very well be misunderstanding the use of trackbacks, and if this is the case, I apologize.)

Surprisingly, a few days later I received an email from someone at ClearContext apologizing for the confusion. They wanted to make sure I understood their intentions, and explained in detail what their survey was about. They also listed a bunch of influential bloggers that were supporting this initiative in some way. In a word, I was impressed.

Since that time, I have had a few email exchanges with Brad at ClearContext, and I have to say that I’ve been impressed at every turn. When I finally took the survey, Brad noticed, and sent me a license for ClearContext for my trouble, even though I’d made it clear that I was perfectly happy with my email solution.

I wanted to make it clear here that I did receive a free license from ClearContext, but that is not the reason I’m talking about their company; I have simply been impressed each time I’ve come in contact with them. I emailed some people I trust about them, and got nothing but glowing references. Therefore, I came to the conclusion that they deserve another try.

So, after my last email-related post where I intricately described my MailFiler / GTD plug-in setup, I’m going throw things into disarray, and turn off MailFiler in favour of ClearContext. I’ll keep you posted on my results.

Seriously; this is must-see video. This guy’s routine is just too damn funny!

Wow; my Filers vs. Pilers post was mentioned on The Gadget Show (a podcast which is part of The Podcast Network) during an episode-long interview of none other than David Allen!

Anyone who knows me or has read this blog for more than a week knows that I believe wholeheartedly in David’s Getting Things Done methodology. How cool is this?

Michael Gartenberg of Jupiter Research puts it more succinctly than I could.

Check out this sordid tale at PocketPCThoughts. Another unlucky purchaser of a Toshiba Pocket PC gets burned. Never again, I tell you.

Why can’t someone, anyone, make a Tablet that rivals the M200? I won’t / can’t bring myself to ever purchase another Toshiba product, so someone else will eventually have to fill my need.

C’mon, Scoble. Stop complaining about being overloaded on your email. If you spent half as long going through your inbox as you do reading your RSS feeds, the rest of us wouldn’t have to listen to you complain. This is getting ridiculous.

Check out this freaking awesome commercial by the NHL Fan’s Association. It hits home perfectly. (This will probably only be of interest to my Canadian readers… haha.)

“When did hockey come to this?”

This is the funniest thing I’ve seen in a long time. The Parents Television Council, which is an organization that is against sex and explicit scenes on TV, have taken it upon themselves to host a page of the week’s best oops, I mean “worst” clips from television. So wait, let me get this straight: Kids don’t have to actually watch entire shows anymore, hoping for a nipple peek here or some heavy panting there, they can just check out a synopsis on the Parents Television Council’s website? How cool is that!

Have you ever wondered how much information sharing goes on between search engines? I’m willing to bet that it’s far more than you think. Check out this wonderful interactive chart showing how various search engines are related to one another.

Hat tip to Steve for the link.

I received a really interesting email last week regarding the use of the Getting Things Done Outlook Add-In along with the MailFiler add-in. I didn’t realize anyone else was doing this, but maybe some people are. And those that aren’t, might want to consider doing so, particularly anyone that is currently using the GTD Add-In and is frustrated with some of its limitations. Our email dialog resulted in the beginnings of this post, which I’ve expanded upon to become sort of my “equation for serious Outlook productivity�, to steal a line from Marc Orchant. By the way, I seriously recommend you read his series of posts by that title.

Both the Getting Things Done Outlook Add-In and MailFiler are wonderful for their own reasons, but unfortunately they tend to fight each other at times. I’ve decided to live with the minor conflicts between the two, but it could be something that would be too annoying for some people.

I absolutely love the Getting Things Done productivity system, but unfortunately it is a little dated, and could use some modernizing. (Merlin Mann talks about this on his wonderful blog called 43 Folders) In particular, for people that receive a particularly high volume of email, it becomes inefficient to have them all lumped together in your inbox, and then try to process them all in order; the user ends up jumping between personal email, bulk mailing list mail, and project-related work email, and isn’t able to focus particularly well on any of them.

What the Getting Things Done add-in is really great for:
1. Turning email into Task list action items
2. Turning email into Appointments (Defer)
3. Turning email into Delegations (Tasks for other people with the ability to track them and remind you to follow up)
4. Grouping tasks by context (Action) and also by Project

What it’s not so good at:
1. Keeping email threads together
2. Automatically filing email into appropriate folders
3. Setting reminders for emails that have already been sent (i.e. alert me if Bob hasn’t responded by tomorrow morning)
4. Giving more control over the inbox, by separating mail into appropriate groups based on the type of mail it is.

Fortunately, all of the weaknesses above happen to be MailFiler’s strengths. In fact, I’d love it if these two Outlook plug-ins could merge to become a sort of “super plug-in”. *sigh*

MailFiler allows you to define a set of what it calls Groups, which are very much like categories. Groups can be set up for any delineation a user might want to make between types of emails they receive. For me, I have the following groups defined: Work, Personal, Hockey, Blog Comments, and a whole host of groups related to specific projects I am working on. (In my day job I’m a project manager.)

The beauty of the groups is that if you receive email from someone that will almost always be related to one of your defined groups, you can have it automatically set to that group upon receipt. With your inbox set up to group items together by their MailFiler “group�, the message will show up in its appropriate place in your inbox. For example, when I receive email from my wife or dad, they show up directly in my Personal group. But when I receive email from one of my clients, it will show up in the project group specific to that client’s project. Neat! For email from people that could be related to any number of groups, you can simply drag it from the default group into the one it belongs in if it happens to be available, or just manually assign it to that group if no other messages happen to be showing in your inbox for that project. That may be overkill for some people, but I love being able to see a group of messages all grouped together for a specific project right in my inbox. If you don’t have time to consider Personal emails, simply collapse that group and don’t look at it. If you’re focused on one particular project, only expand that group in your inbox.

As I mentioned above, when you use both the GDT Add-In and MailFiler together, there is some conflict that goes on. The main conflict occurs because MailFiler actually tracks message threads with a unique identifier in a separate database, and goes to great efforts to ensure that messages from the same thread stay in the same folder together. Unfortunately, the Getting Things Done plug-in attempts to do some rudimentary email filing help, and it almost always conflicts with the filing system being used by MailFiler. This results in MailFiler constantly popping up messages asking questions like:

There are 5 messages in the thread "Baking chocolate and pickle pies" filed in the folder "Baking".
Would you like to move them into the @Action folder?
[Yes] [No]

This occurs when the user decides that the message they are reading should be turned into an Action item (an item in their task list) and clicks the Action button in that email’s window on the GTD toolbar. GTD at that point takes a copy of the email, and moves it into the @Action folder under the Inbox, presumably to make it easier to find. Unfortunately, MailFiler detects a new message in the same thread, and wants to move everything in that thread into the @Action folder to keep the thread together (i.e., all previous 5 messages about baking that disgusting pie). It’s perfectly fine to answer “No” in this instance. What this means is that for that message that went into the @Action folder, the relationship between it and the other messages in the same thread is broken. That’s okay though, since it was simply a copy of the original. Annoying, yes. But it doesn’t break MailFiler’s functionality.

Where I really find this system shines is when I have created a task from an email using the GTD add-in. One of the buttons on the GTD task toolbar is “Open Mail”, which will open the original message that the task was created from. Of note is that it appears to open the version of the message that you filed in the correct folder, rather than the one in the @Action folder. And this is a Very Good Thing. It’s a GREAT thing in fact. Why? Because once you’ve opened that originating email, there is a button on the MailFiler email toolbar called “Thread”. This button is probably my favourite button in Outlook. When you click that button, you get a tree view listing of every email in your system (both going out and coming in) related to the thread for the message you’re on, even if the subject line has been changed. The tree view is wonderful, because it allows you to see instances where one message may have received multiple responses, or a conversation has taken a tangential turn, and has resulted in a branch. With one click, the user can instantly see every message on their system related to that specific task item, and their relationships to each other. Clicking on any message in this tree view pops open the actual email. Perfect!

There are other features in MailFiler that are interesting, but that I don’t make use of. MailFiler has a system for organizing projects, but I find it much nicer to simply use the GTD methodology. I think I could probably integrate them, but I’ve found no need to based on the combination of the “Open Mail” and “Thread” functions described above.

So that’s my current system for email productivity. It’s not perfect, and I will be tweaking it as time goes on. But for now, this is the best way I’ve found to keep control of my inbox, and my task lists.

I’d be remiss if I didn’t also mention that a good Desktop Search application is a must for any serious Outlook productivity system. I’ve discussed Desktop Search applications previously (at the bottom of this post), and luckily there are some very good free ones available.

I also use some of the other utilities Marc mentions in his Equation for Serious Outlook Productivity series of posts, like ActiveWords, Anagram, and NewsGator. But this post is already far too long, so I’ll have to come back to those later. For an idea of what they’re all about, check out Marc’s thoughts.