A key element of personal productivity is tracking one’s tasks. I use Microsoft Outlook and it strikes me that doing so is harder than it should be. And from dealing with this apparent limitation, we may be able to draw a lesson about personal productivity more generally. 

Lawyers are busy and typically need to keep track of a myriad of tasks. For those who are organized, it can be handy to track task by a priority, client, date, degree of completion, who requested it, and so forth. Some tasks may be linked to one another or sub-tasks of others. In techie terms, this means one can view tasks as either a database or a hierarchically nested outline.

A product – now defunct – called Ecco Pro allowed organizing tasks both as a database and as an outline. That was in 1994! Today, Outlook provides what are, in my opinion, primitive features for managing long task lists. Last year I spend a fair bit of time pushing Outlook features. The best I could come up with was to re-name some native fields for projects (matters), importance, and comments. Then, using the “Group by Box” feature and different views, I can see tasks arranged by my fields. Confusing? Of course it is. It took me a while to figure out these features.

I found investing the time to do so had paid off, but this raises questions. First, have I missed something basic about using Outlook? Second, am I crazy to want to organize my tasks along these multiple dimensions? Third, should I have looked for a different software package? And fourth and most importantly, what does this say about personal productivity?

That last question really subsumes the first three, so let me take a crack at answering it. Sometimes improving personal productivity means making a reasonable investment of time. But sometimes the better approach is to accept inefficient ways because the software is too hard to learn. The key is to know when the problem is the software and when the problem is user inertia. Unfortunately, it is not always so easy to know which is which. I have argued previously and still believe that users need to do more to improve their own know-how. But there are clearly areas where software developers can do better.

By the way, I welcome any feedback on the question of how to manage tasks better.