Task management: Some improvements

I am a highly organized person. (Some might say too organized.) But I am always looking for ways to improve my organizational systems.

I live by my to-do list, which I use Outlook Tasks to manage. Because I manage several different projects at the same time, my task list helps me keep my place in the different project plans. Here is how I used to create my task list:

1. I created a master project plan, usually in Microsoft Project.
2. Because we use iterative development methodologies, I broke my project plan down into iterations.
3. I copied the full set of tasks for the next iteration onto my Outlook task list, set due dates for each based on the project plan and categorized each by project.
4. I prioritized each task based on criteria like the priority of the project, hard-and-fast deadlines versus moving targets, and so on.
5. I used the status to distinguish between different types of tasks, such as Deferred if I couldn’t start the task until a particular date and Waiting on Someone Else if I couldn’t start the task until I had received something from someone else.

Then I organized my Outlook Tasks view to sort tasks by priority and status so my highest priority tasks that I could begin work on immediately were always at the top. The theory was that whenever I looked at my task list, the top one or two tasks would be the ones I would most need to work on, even if they weren’t technically due for some time.

Why was this not working? Well, I had way too many tasks on the task list. Due dates are hardly ever set in stone and dependencies keep changing. I couldn’t keep up with the changes very well because there were so many tasks to update, so tasks kept going overdue. Pretty soon, I had a list more than a screen long, many of the tasks red because they were “overdue.” The result for me was paralysis — I didn’t know what I should be working on. I was spending more time managing my tasks than doing them.

Then, as I was surfing through the blogosphere, I came across this very simple principle: Each task should be a discrete action that you can perform ideally in one sitting. (I don’t remember which post triggered this insight, unfortunately, but I’m sure it was while I was reading up on the Getting Things Done methodology.) In other words, the task should not be “launch the website” because there are really several actions that need to be performed to accomplish that goal. This is very similar to identifying actor goals for use cases.

The correlating principle is this: Once an action is completed, it should generate a new follow-on action. The same is true when a meeting or a phone call is held — new actions should be generated from that. The only exception would be when a deliverable is delivered and no further followup is necessary.

Based on these two principles, I cleared out my tasks list. I went through all my project plans and identified the next actions I could take for each. These usually involved looking at the next task I had identified for that iteration and asking myself, “What specifically do I have to do to get started on this?” Those next actions I put on my task list, but nothing more; often, I would make notes in the task screen about what the next steps might be so I wouldn’t have to keep referring back to the project plan every time I completed an action, always keeping in mind that next steps are flexible.

Now, each task on my task list is something I can reasonably complete in a few minutes or a few hours — no more than a day. Whenever I complete a task and check it off, I immediately create the task for the next action. Also, whenever I attend a meeting or have a phone call, or I get an email with a new request, I add all actions generated by that to my task list immediately afterward. On a regular basis, I update my project plan with the notes from all completed tasks and make sure I’m adhering to the plan, while incorporating any changes that might have come up (the first principle is always to be adaptive). As a result, I am keeping a very detailed record of what tasks we did, how long each took, and how and why we had to deviate from the original plan for later reference and learning.

The result? I have a very lean to-do list that doesn’t overwhelm me when I look at it. I am easily able to cross off my tasks for a day, which gives me a sense of accomplishment and satisfaction. I find that I am more flexible at dealing with new needs and requests as they come up. And I am keeping better notes on my projects’ progress.

And I have more time for blogging…