In a previous post I talked about my quest for an empty inbox and all the tools I tried along the way. Well, I’m at it again. My previous tool of choice, Taglocity, has taken a turn toward online social/collaborative email in their 2.0 release. I’m afraid that 99% of the email I handle is work related, and our big lumbering IT department would never allow a rogue server, inside or outside the firewall, collecting corporate data. Likewise, getting said lumbering IT department to establish their own server would be equally unlikely. The social/collaborative approach might be the next big thing, but I need help now. The final nail in the coffin was that some of the features that originally sold me on Taglocity 1.x are no longer supported in their 2.0 beta release. Given the new direction, those features won’t likely return.

So where does that leave me? Well, I went back to my notes and started to think about what kind of help I really need. Here are the requirements I came up with:

  1. Need a quick way to triage and file email. Filing must be effortless, otherwise I will resist doing it
  2. Needs to be a stable tool that works well with Outlook 2003 (yes, I’m still stuck there… see comment above related to the big lumbering IT department).
  3. Need to strip out the spam and low-priority reference email & notifications
  4. Need reminders for my own actions as well as follow-ups for requests I send to others
  5. Must fit into my GTD workflow… In general, that means I need a way to create tasks and appointments from email and somehow tie related tasks/emails/appointments/notes together to form a “project”.

After recasting my net and re-evaluating the latest versions of all the tools I had previously considered, I came across a gem that I hadn’t given a chance the first time around: ClearContext IMS. It seemed to meet all of the needs I described above, and there was even a trial version available… Off I went.


After using the tool for over a month now, I am starting to see some nice benefits from the various features. Here’s a look at the highlights as well as some improvement opportunities for the ClearContext development team…

FILE MESSAGE, FILE THREAD. ClearContext does a fantastic job with filing (my #1 requirement above). One of the best features is being able to bring up the topic selection dialog (ALT-P) and type just a few characters of the topic name to narrow down the list. ALT-M will file it from there (no mouse required). What is especially nice is that your don’t have to remember any prefix or top level folder name since a match even in the middle of the topic name will select it. Additionally, You can choose to file the original message while typing your reply right from inside the reply window. Nice touch!

Two needed improvements for topic filing are:

  1. Please, please, please guys add a confirmation dialog when I type a topic name that doesn’t already exist. 90% of the time I do not want to create a new topic, I just mistyped an old one. When that happens, I have to manually drag messages around and delete unwanted topic folders.
  2. Change the search behavior of the drop-down topic selector in the main Outlook explorer toolbar to behave just like your topic selection dialog box. Typing a name in the drop-down selector only selects topic names that begin with those letters, so it is not nearly as useful as it could be.

DASHBOARD. This feature really ties things together. None of the previous tools I used could do this. You can see your tasks, appointments, and only your flagged emails. To minimize the clutter and help resist the temptation of constantly checking your inbox, I would recommend the following:

  • Open a separate window by right-clicking one your Inbox and selecting “Open in New Window”.
  • Select the Dashboard from the ClearContext toolbar to turn this window into the Dashboard window.
  • Finally, turn off the left-hand pane (folder list) by pressing ALT-F1 or un-checking “Navigation Pane” in the View menu.

To quote the voice inside my head, “My inbox is a nice place to visit, but I wouldn’t want to live there”. To this end, the ClearContext Dashboard view helps me focus on my tasks and not my email.

RELATED VIEW. This feature compliments the Dashboard well. Basically, you can see all tasks, appointments, and emails related to the item at hand. For many tasks, I often find myself copying 5-6 email messages into the body of the Outlook task just so that I have the reference material handy without having to search. This method obviously doesn’t scale well for longer-term tasks or for those with lots of active email discussion. It also adds painful extra steps to my email filing process, resulting in constipation of the Inbox. The ClearContext “Related View” button solves this issue by giving me one button to display all related messages, whether they reside in my Inbox or in one of my topic folders.

One tip, however… be sure to create your tasks using the ClearContext “Task” button inside the email window, otherwise the tasks will not be linked. An improvement request for the ClearContext developers: Give us a way to add items (such as previously created tasks) to a “Related View”.

FOLLOWUP MSG. This button is available to you when sending an email, and I find it to be one of the handiest features in ClearContext. First of all, it puts the follow-up task on your task list where it should be. It also gives you the option to have the task automatically close if you receive a any reply or a reply from a specific person… very clever!

DELEGATE. I actually do not use this feature. In one mode, it allows you to turn a message in your inbox into an Outlook-managed delegated task. I find Outlook delegated tasks to be one of the most obnoxious features of Outlook. They say to the recipient, “I didn’t care enough to come talk to you, let alone send you a proper email. Now do my bidding!”

There is another way to use the ClearContext Delegate feature which simply forwards the email and creates a follow-up task in your own task list. This is nice, but it is essentially the same as using the Followup Msg button described above, only with fewer options. Because of that, I just use the Followup Msg button instead of the Delegate button.

PRIORITIZATION & SCORING. This is one of the most publicized features of ClearContext but, to be honest, I haven’t used it at all so far. Instead of the priority approach I just try to minimize the amount of email I need to touch as much as possible. I set up filters to clear spam, I unsubscribe from as much stuff as possible, and I set up rules to file status & automated emails from other tools. I may explore prioritization a bit more in the future.

DO NOT DISTURB. I found this feature to be only marginally useful. I contend you should always have new mail alerts disabled… I would recommend turning off Outlook alerts in the options panel:
1. Select Tools –> Options, then the Preferences tab,
2. Click the E-mail Options button, then the Advanced Options button.
3. Uncheck everything under the heading “When new items arrive in my Inbox” as shown below.

ALERTS. If you are following my advice above and have disabled Outlook email notifications, it is possible that you might miss an important message from the boss. Sure, there are ways to still see Outlook message alerts for special cases, as described in this article. The ClearContext implementation, however, is a bit smarter than what comes in Outlook 2003. First of all, you can specify a time limit before it nags you. Secondly, you can quickly create a new alert from a selected message. The trigger can be based on the sender or the conversation/thread. Finally, you can have a big list of alerts without cluttering your Outlook rules, or exceeding the max size limit, which is only 32kb for Outlook rules.

AUTO ASSIGN. Here is how you can greatly reduce the volume of junk that pulls on your attention. Set up as many rules as you like, go crazy, don’t hold back. Ruthlessly have email automatically filed to your topic folders without having to ever see it. Don’t worry, you will still be able to find everything through desktop search. Just like with the ClearContext Alerts feature, the Auto Assign feature allows you to create rules from the selected message. It auto-populates the sender’s address or domain, subject line, etc. This feature also keeps you from hitting the Outlook rule size limit I mentioned above.

Two improvement requests for the folks at ClearContext:

  1. Integrate a simple Bayesian auto-assignment engine that can optionally be used (and trained) to assign topics. Two good open-source choices would be PopFile or CRM114.
  2. Allow auto-assign rules to also move items to the Outlook “Junk E-mail” folder (outside of the topic folders). With the current implementation, I have to create my own “Spam” topic folder and handle it separately from the Outlook “Junk E-mail” folder.

TAGGING. Okay, so what about tagging? The whole notion of tags is big part of what sold me on Taglocity, and ClearContext (as of this writing) doesn’t support multiple tags. I came to a stark realization: After using Taglocity for over a year and studiously tagging my emails with 3-4 tags each, I only used those tags 2 or 3 times to find an email. The truth is that desktop search trumps tagging every single time. Adding the tags was just a trick I was playing on myself to make me feel better about filing all of my email in one big archive folder. Somehow, having those tags on the emails made me feel “safe”. In reality, neither the tags nor the folder structure mattered because if it wasn’t in my inbox, I was going to find it through desktop search.

ACTIVE FORUM. What? How is this a feature? Well, it may not be a feature of the tool, but it’s definitely part of the overall experience. Having a well-run active forum that gets regular participation from the support staff is a huge plus. ClearContext definitely has this going for it in their forum.

PRICE. Okay, this is also not a true feature, but an important consideration nonetheless. As I mentioned once before, I’m not just thrifty, I’m downright cheap. I don’t like paying more than $29 for any productivity tool. The bad news is that ClearContext IMS currently sells for $89 per copy. Ouch! The good news is that they are working on a free Personal Edition, which is now out in public beta. As competition heats up, hopefully the price for the full-featured version will come in line. In the mean time, you can request a copy of the Personal Edition here.

Some additional good news – There is a coupon code for a limited time… details here.


Ok, so I can’t sign-off without a few words about how ClearContext fits into my GTD landscape. When I first started using the tool, I read through the on-line help and tutorials, and I downloaded their PDF guide for using ClearContext with GTD. The guide is handy. Now, the recommendations don’t have GTD’ers using the tool differently than anyone else, so in that respect it reiterates what’s already in the on-line user’s guide. It does, however, provide some key concepts to make sense of what the tool already provides:

  1. ClearContext “Topics” = GTD “Projects”.
    This should not be too hard to remember since the topic assignment shortcut is ALT-P. That’s “P” as in “Project”!
  2. Continue to use Outlook categories as GTD “Contexts”.
    In the past I have tried using other Outlook fields for context information since you cannot sort on the Category field in Outlook 2003. A word of advice: Go with the crowd on this one and don’t fight the tool. Do use Outlook categories for context information. There are a number of built-in features & forms in ClearContext that allow assignment of an Outlook category.

One other big “ah-hah” that took me a few days to discover is to treat the messages in your topic folders as done/processed. Initially I wanted to treat these topic folders as a pre-sorted Inbox, similar to what I had when I was using PopFile with Outclass. If you use that approach, however, you will again be fighting the tool. Keep your Inbox as your Inbox, process the items quickly using the four D’s (Do, Delegate, Defer, or Delete), and let your topic folders be your archive.

One additional tip related to the topic folders: Start with a handful of high-level general topic folders. These could be major areas of focus, or roles/responsibilities you have. Underneath those, create a single level of short-lived narrowly targeted project folders. File miscellaneous messages right in the top-level folders. File messages related to a specific project one level down. If an email chain starts to turn into a longer-term project, simply create a new folder and drag those messages down into it. Create as many of these as necessary keeping one folder per project. This structure can then serve as a backup to the Related View button and allow you to quickly find everything related to a given project.

That’s it… 30+ days, and I am still happily using the tool. In a future post I’ll share some of the detailed settings & preferences I am using, as well as my take on additional features that I didn’t mention here. Until then, go download an evaluation copy and try it out for yourself!