Email Categorization. By using predefined filters and a handy drop-down list of existing categories, I could quickly and easily label the contents of my inbox.

Portable Changes. I sync to a Windows Mobile device, and ClearContext works it’s magic using a combination of folders, categories, and probably other things, so that while the ClearContext features are obviously missing on the pda, everything is still readily usable and syncs back and forth without issue. I’ve used another Outlook add-on in the past that made so many proprietary additions to Outlook that syncing was an absolute nightmare and the mobile device ended up with a complete jumble of information.

Threading! Decent threading in Outlook. A miracle, I know! Due to the limitations of Outlook (see above) the threading feature isn’t as good as Gmail’s, but it’s still a HUGE improvement over Outlook’s default capabilities. (Microsoft? Are you listening? You REALLY dropped the ball on this one.)

Clean Inbox. Once an email has been assigned a topic, I can instantly file away that message, that thread, or even the entire topic. I LOVE this feature! I can go through the inbox, processing and reading, then clear everything away with a couple quick presses of the file button.

Convert Email To… This is another big time saver, ClearContext can instantly create a task or appointment from an email message (while also linking them) and even tries to pull the needed information from the body of the message, while copying the message contents to the items notes field. Revolutionary? Probably not, but a big convenience regardless.

Other There are a ton of other useful features from ClearContext, and while I use some of them the ones listed above are what really made a big difference for me. From reading the ClearContext blog it looks like there’s lots of exciting new features and improvements in the pipe, and visiting the ClearContext forum it looks like they really take customer feedback to heart.

Shameless Plea Despite all the improvements made to Outlook by ClearContext, it does have one downside. It’s, well…. expensive. At $90 for the full version (with many of the features above) I’m finding it hard to make room in my college-student budget after ramen and the occasional beer. Thus my most pressing feedback for ClearContext becomes to offer student pricing, or some sort of similar discount. And if someone from ClearContext happens to come across this (completely unsolicited) post, and would like to “donate” a license so that I can continue to evaluate new ClearContext features, I REALLY wouldn’t say no!

All shamelessness aside, between the new features of Outlook 2007 (To-Do Bar especially) and ClearContext I’m the happiest I’ve ever been with my personal information management system, and it just wouldn’t be possible without ClearContext.

The presentation focused on the following topics.

* Best Project Tools
* Best Office Tools
* Best Email
* Best Calendar
* Best Collaboration Suite

As with much of the current Web 2.0 world, many of the apps he recommended were in Beta or even Alpha but all appeared to be capable tools none-the-less. Throughout the discussion I kept looking for solutions I could bring into my own world including my corporate employment, ongoing college education, and personal projects, and while I could see plenty of uses for the last two it was the corporate settings that came up short. None of the tools seemed to have support for the centralized administration and control that is common in my organization and while workarounds are possible they would require a lot of manual intervention.

This raises the possibility that it isn’t the tool that is broken but rather the way my office works that is ineffective, however the effort and time required to convince and then train hundreds of people in a new way of working would be so extensive as to rule that possibility out, requiring that the tool integrate with the way we already work for better or worse. I say this as my employer rolls out Sharepoint across the organization which is a new way of working and collaborating that will require extensive training, so perhaps I am mistaken? I also wonder if it has to be an all or nothing proposition, might there be a way to use these tools alongside existing corporate apps and get the best out of both worlds? Could a free Basecamp account be used to supplement an existing Sharepoint collaboration site?

The issue that I haven’t seen addressed by either Sharepoint or the Web 2.0 apps here are the interrelated problems knowledge retention and interoperability. What happens when an employee leaves and takes their Basecamp account with them, including project records and notes that may be needed for years to come for reference and billing questions? How can I take the data from one application and move on with it to another application, or even within the same application? For example, what if I have a personal site setup in Sharepoint being used for a small project I’m working on which is then merged into a larger project involving several people with their own Sharepoint site? Is it possible to move a project from one Basecamp account to another? I don’t believe any of the solutions offer an export functionality, other than RSS or iCal. And it doesn’t matter how much you can export from one service if you can’t then import it into another. All applications get replaced over time, and less and less time in our rapidly changing landscape, so it is imperative that the data can outlive the application.

Shortcomings aside, the tools discussed still hold a lot of opportunity for informal and flexible teams if being less attractive to rigid and slower moving corporate teams. I think the current tools are most useful to small entrepreneurial businesses who can now replace an entire corporate IT office with an internet connection and browser, allowing more focus and time to be spent on the product. This is an exciting time with more quality tools available then ever before and I look forward to seeing what the future holds.