Native Windows (offline-capable) softwareScope 
While there are a great number of ways to put a Getting Things Done system into action on a Windows PC, I'd like to compare and contrast the benefits of using native Windows software like Outlook (arguably the most popular personal information management software on Windows) and handheld computers (in this case a Pocket PC) versus using online web-based software. Today's post will focus on the "offline" native Windows and Pocket PC software.
Quick Overview of GTD ConceptsIf you've read the Getting Things Done book, or are already familiar with the system, feel free to jump to the next section.
Almost all geeks that are interested in any way in productivity and productivity software have probably heard of GTD, or Getting Things Done. GTD is a productivity system developed by David Allen for busy executives, which has achieved a certain cult-like status amongst geeks. Many popular blogs like
43Folders and
Black-Belt Productivity have popped up over the past few years and have become extremely successful discussing different approaches to the GTD system.
In it's most basic form, GTD is a system for helping to collect, organize and act on your thoughts and outstanding "to-do" items. It can be implemented completely using paper and pen, but obviously this isn't what appeals to most geeks.
Briefly, GTD teaches you to collect all of your incoming information into a single location (inbox), then deal with each incoming item only once, choosing exactly what to do with each item at that time (processing). Note that it's important to note that the act of collecting should be separated from the act of processing - this seperation is an integral part of the GTD system. Finally, GTD teaches you to perform a weekly review, to ensure that all of the tasks you are tracking are up-to-date, and that you have a sense of everything you are attempting to keep track of. For a
visual description of this process, you can download a free PDF. To download this PDF, you will need to register with a valid email address. (I know - PITA).
Finally, what is the point of all this? Getting Things Done's main point is that if you can collect all of your outstanding to-do items and random "oops, I should..." thoughts and write them down in one location, your brain can relax and stop trying to track them all. This allows you to actually focus on what needs to get done. There is also an element of determining which project a given task belongs to (or if it is itself a project), and what context the task can be performed in. The concept of contexts is another discussion altogether, but it's important to keep it in mind since there are varying ways to track context in different software applications.
The Pleasure and Pain of Microsoft OutlookWhile it holds the status of most-used email and productivity application on the Windows platform, it's arguable whether this is because users love using it, or that they're simply required to use it by their company. In fact, there are probably thousands of users in both camps. Either way, if you're an Outlook user, it's worth learning Outlook's quirks and capabilities as completely as possible to put yourself in a position to get as much as you can from the application.
For users that would like to configure Outlook manually to support the GTD System, David Allen's company has released a PDF document (available for $10) that walks through 37 steps to
set up views that make the most of Outlook's built-in functionality. If you're not sure manual configuration is for you, check out the
free sample excerpt from the full document (links to PDF file).
The great thing about this step-by-step tutorial is that it will probably teach you things about Outlook that you've never seen or done before. The downside is that it's quite involved, and if you're simply interested in putting a system into place, you'll be frustrated by the amount of manual configuration, and some of the limitations of Outlook, when used without any add-in software.
Outlook Add-InsOfficial GTD Outlook Add-In 
The David Allen Company advocates an official
Outlook Getting Things Done Add-In that will create all of the views referenced in the manual-configuration article mentioned above, plus a number of additional ones. But more importantly, it builds some additional logic into Outlook to make it easier to track a task as a child of a parent project.
The GTD Outlook Add-In also adds a toolbar to your Outlook message windows allowing you to make a task from an email, and assign it to the appropriate project and context tracked using Outlook's built-in categories as well as a dedicated context field. This is done so that PDA users will be able to see their tasks grouped or filtered on context.
While the add-in accurately supports the GTD methodology (not surprising, since it's the officially sanctioned add-in), it is surprisingly more cumbersome to use than you might expect, and not at all user-friendly in many aspects. Although the developers have thoughtfully included keyboard shortcuts for most of the actions you might like to perform, often the keyboard shortcut is actually the only quick way to perform it. When you fail to remember a given shortcut, you find yourself digging around in dialog boxes.
Unfortunately in my experience the official Getting Things Done Outlook Add-In seemed to cause instability and performance issues with Outlook's PST file on my machine. To be fair, the last version I used was from at least a year and a half ago, and we all know how far software can advance in that period of time. I don't mean to unfairly knock the official GTD add-in, I'm just describing the experience I had with it.
ClearContext 
Another Outlook add-in option, and the one that I'm currently using, is called the
ClearContext Information Management System. ClearContext's latest version (IMS 2.0) contains similar GTD functionality to the official add-in, however this functionality only scratches the surface in terms of the power that ClearContext wields. Although it's outside the scope of this article, let me say that if you ever struggle with keeping up with your email and you are an Outlook user, it is definitely worth your while to investigate ClearContext further. The prioritization engine and inbox views are pure gold.
Back to the Getting Things Done functionality, you'll note that ClearContext uses slightly different terminology, calling projects "topics", but the end effect of this is that it makes determining the project that a given email belongs to exceedingly simple.
Like the official add-in, ClearContext adds toolbars to both the main Outlook window and message windows to make it easier and more intuitive to act upon your messages. Functions like turning an email into a task are the bread and butter of ClearContext's GTD functionality, but it shines in that it can accurately track all emails that relate to a specific task, and present them to you in a list at any time. Even better, this even works with emails that have not yet or never will be assigned to a task.
PDAs - Pocket PC & Palm Probably one of the biggest benefits to implementing your Getting Things Done system in Outlook is the ability to then synchronize your task lists to a handheld PDA like a Palm or Pocket PC. Unfortunately, since Outlook does not have a built-in method for tracking the project that a task belongs to separately from the context it belongs in, most GTD methodologies are at least a little bit limited when synchronized to a PDA. In most cases, this doesn't break the system, but rather makes your ability to work with tasks slightly limited when using only your PDA. Of course, this limitation can be easily overlooked when faced with the convenience of being able to review your task list anywhere, anytime.
Although I have no experience with using Palm devices, I do have quite a bit of experience with Pocket PCs. Unfortunately, while it is functional, Microsoft's built in applications for dealing with your tasks and calendar leave quite a bit to be desired. This has produced a booming market segment of 3rd party PIM software dealers for Pocket PCs. My preference is
Pocket Informant, although by all accounts
Agenda Fusion is also a very good choice.
Wrapping up GTD in "offline capable" softwareFor some people, implementing Getting Things Done in native Windows software like Outlook is the only way to go. By far the biggest benefit to using software like Outlook and a PDA is the fact that you simply don't need access to an internet connection to work your system. People that travel frequently or simply find themselves on the go will appreciate this.
Check back for the second and last (at least for now) part in this series, where we'll discuss the options available to set up a Getting Things Done system using online software. And yes, I'm talking about all that Ajaxy goodness that is making online software more and more viable for everyday use.
