Using GTD and Outlook to Organize Projects & Tasks for a Small Business

“Getting Things Done,” By David AllenAs the project manager for a small company, one of my biggest responsibilities is to make sure projects are on track and that clients are satisfied with our work. I wrote a three-part blog post on using a Web-based project-management tool to organize tasks and projects. Project Insight has helped us see how much time we are spending on each project and what outstanding tasks remain.

One thing it has not done for me personally is to help me organize my daily tasks. I am a big fan of David Allen’s Getting Things Done methodology. (Here’s a link to one of my favorite overviews of GTD). Since we use Outlook as an organization, I have been looking for the best way to integrate Outlook with GTD.

GTD Workflow Chart

Basically, GTD is a way of prioritizing your tasks–and your life– to free yourself up to actually do things, rather than worrying about all of the stuff you have to do. David Allen has a workflow chart that I–and many other GTDers– use to decide how to prioritize what he calls, “next actions”.

GTD fans will reflexively reply that there is a David Allen-approved GTD plug-in for Outlook. Yeah, I know. I’ve used the demo version, and haven’t been impressed enough to spend my own money to buy it, or to grovel to my boss and ask him to buy it for me (but if he’s reading this, hint hint…j/k).

I’ve spent a fair amount of time looking for a free alternative to the GTD plug-in.

Here are my requirements:

  • Projects: I want to be able to create projects. I want to be able to take tasks that I’ve downloaded from our Project Insight system into Outlook and add them to projects. As an example, one of the projects I have for myself is to “Integrate [client’s] site with Google Website Optimizer so that we can create landing pages for specific PPC campaigns and for B2B SEO.Here are the tasks I have for this project, along with their contexts (sorry, non GTDers, this is pretty specific lingo that will have a different meaning for you once you’ve read the book… assuming you’ve made it this far in my blog post).GTDers will note that my contexts are outside the norm; because I spend my day in front of a computer @computer means little to me, so I have contexts such as @email, @ProjectInsight, @searchWeb, etc. 43folders also has a nice post on contexts.
  • Create Requirements Document for Developer: @Email
  • Developer adds code to page: @Waiting On
  • I create special landing page: @Dreamweaver
  • I test page: @Web
  • I push page live: @Web
  • I test analytics integration: @Web
  • Customers line up to give our client their money: @Dream

Yeah, okay, that last task is a joke. I’m a funny guy. Really.

  • Next Actions by Project: I want to be able to identify my next actions by project so that I can scan my list of projects and see what the very next thing to do is.
  • Next Actions by Context: So, I’ve decided to spend an hour doing@Web tasks. I need to know my next actions that need to be done on the Web.
  • Waiting On: Who owes me what? A lot of what I do is ask people to do things for me… clients need to implement our recommendations… coworkers need to run reports… tech support reps need to tell me why the thing I need to do can’t be done, etc.

So, over the past six months or so I’ve been trying various methods.

  • First, I tried the trial version of the GTD Outlook plug-in. It’s okay, but I don’t think it’s worth $69.95. Plus, who know when they’ll make a new version and force me (or my boss) to pay another $70.
  • Then I tried a freeware program called Jello. This is a truly nice product. It turns the Outlook home page into something (horrors!) useful. But, it has a ways to go. I’m not complaining, mind you. It’s free and the developer has clearly put a lot of time into the tool. I’ve posted comments and suggestions and he’s taken the time to reply to me. I would love to be able to use this all the time. But at the moment, I find it a bit cumbersome.Update: I sent the Jello creator a draft of this post to get his feedback and he was nice enough to send me the version 4 alpha of Jello, which I have been using for a day now. It’s great! I have some more questions, but at this point, I am ready to say this is the system for me.
  • I stumbled upon this great blog post by a Microsoft employee, David Ornstein. He seems like a really nice guy and his ideas show a lot of imagination. It took a long time (several hours I’d say) for me to fully implement his system.I had to copy and paste VB script and make custom rules and on and on. It felt like I was performing surgery on Outlook and I wasn’t quite sure the patient was going to survive the operation.But in the end, his system has been great for me.I use Outlook 2007’s categories as contexts, so that I can label an incoming message as a “Next: Computer Work” task, etc. This works for things I am waiting on from others as well.The major drawback to this is that I have not found a way to create projects such that I can drag and drop tasks into the project and see which task go with which project. The result is that I have a long list of next actions divided by context, but not by project.
  • Simon Guest GTD methodologyThere is a similar methodology by Simon Guest, a Director in the Architecture Strategy Team at Microsoft. I like his process, but I do not find it convenient because he denotes both contexts and projects by using the Outlook categories feature.This means that each action is a member of two categories, one for its context and another for its project. I personally find that confusing.
  • In another Google search, I came across a page titled, “Managing GTD Projects In Outlook”. Sounds perfect, huh?! I hungrily read the entire page and got to work implementing the suggestions. Basically, the idea is to create a template based on the Contacts template and use it for projects. The author even has a template you can download. After you follow the (not so) easy seven-step process for adding new templates, voila!

Unfortunately, I am using Outlook 2007, and this is written for Outlook 2003 (the page says, “This page last updated 29-Sep-03” by way of apology or disclaimer, I guess.) In infinite Microsoft wisdom, templates created for Outlook 2003, don’t work for 2007. What a difference four years makes!

Since then, I’ve been searching for a version of this template that DOES work with the new version of Outlook… but so far, no luck. So what am I doing to organize my tasks? I have been using a hybrid system that incorporates David Ornstein’s suggestions along with Jello.

Now that I have the latest alpha version of Jello, I am going to try to migrate everything to that. I truly this could be the best system for me.

I would love to know how other GTDers have solved this problem. I’ve done a lot of Web searches, but haven’t found something that everyone can agree is a good idea.

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  • Thanks Josh for your kind words about Jello.

    I think you need a perfect GTD system for this kind of work management and I totally agree with you with the existing solutions you present.

    Before I starting developing Jello, I read all this stuff, and tried a lots of things. None of those did the trick. And my needs were strictly personal. If I was in your position I would be totally confused!

    And Jello started just to serve some personal simple GTD stuff but having this input by people who use it at work I got tons and tons of ideas and features to add in it.

    And I think your goals are realistic! Any man trying to apply GTD at work should have the ability to do all those basic stuff. Because its basic to GTD.

    I think your post is pointing exactly where you wanted. The lack of professional GTD systems.

    I hope to continue having you around for your feedback to make a better application!

  • Michael

    Hi there,

    I’m still condemned by my employers to Outlook 2003, so perhaps this comment is no longer relevant… But here goes.

    I was interested in your point about using categories as contexts, but being unable to create projects.

    I use categories for both projects, contexts and other things. a @ prefix denotes a context, whilst, for example, ! denotes checklists and other lists that don’e require immediate action (Eg !Someday and !Waiting) I use £ (you could use $) to denote things i want to buy/have bought for me, Eg £books or £CDs or, simply, £Gear. Then, in category view, I use the importance flag to mark Next Actions with the red exclamation mark (and ONLY Next actions!)

    The power of this system comes with the ability to customise the view in the taskpad, thanks to the fairly potent filter functionality, and to save these views as a sort of menu in taskpad. Examples of views that I use a lot: Next actions @[context of choice], @Calls, !Waiting… you name it…

    Annoying things: the categories interface is a primitive afterthought, whilst it *should* be the cockpit of the whole thing, and it is annoying that you can’t get rid of Outlooks default taskpad views.

  • Your comment makes a lot of sense, especially as it relates to using categories for projects and contexts. Simon Guest’s post ( may be of some value to you, if there are ways to implement some of his suggestions in Outlook ’03.

  • Sonal Bansal

    I came across this other commercial tool which allows you to implement GTD in Outlook.

    I’m only trying it myself right now. Just thought I’d pass it on to you as well 🙂

    Thanks very much for a very informative post.

  • Sonal Bansal

    Apologies … forgot to mention the tool.

  • Chris H

    I also have tried many of the things you have tried. Outlook 2003 with add in options, custom VB Script, jello (great functionality but the performance was slow), as well as completely seperate tools like wikis and standalone spreadsheets. With Outlook 2007 now available to me I am back in Outlook. For my tasks I use a project user defined field to capture the project name and use the categories to define context. I have two task views I which groups by categories and sorts by project and one which does the reverse. This is working well for me allowing me to quickly see my tasks both ways depending on if I am focusing on the project itself or my available contexts. Good luck on your productivity journey.

  • Barry

    I recently moved to Outlook 2007 and also looked to implement David Ornstein ideas for using GTD . Great stuff, but have the same problem regarding projects.

    To solve the problem, I have been experimenting with creating folders for each project and adding the “in folder” field into the to do view to organize to do’s into projects. I then created shortcuts for each folder so I can drag and drop the to do items into the projects. Still a work in progress, but it seems to works pretty well. Hope you find this helpful. Would welcome any other ideas.

    (Note: I purchased the GTD add-in years ago and have been using it on and off until this last upgrade. The tool is OK, but never was able to really get it working smoothly, there were so many little things that made it feel clunky. I just couldn’t bring myself to reinstall it on my new machine.)

  • Gabriel

    Hi Josh,

    Now that you’re using jello.dashboard 4, would you mind writing a blog post on how you use it and structure it vis-a-vis native outlook features such as categories and folders? It would be really inspirational and of great help to see how others go about using gtd and jello.


  • Brian

    Josh — I too am curious about your experience since your original post.

    Great post on the subject and your research. Very helpful.

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