Everything we do, day in and day out, can generate data, which can be leveraged to create better estimates. In fact, the more “stuff” we do, the more data we generate and the more useful it becomes.
Each and every one of us estimates poorly in our own unique way. Some of us over-estimate, some of us under-estimate, and some of us couldn’t hit the broad side of a barn. However, we usually follow a pattern of some kind. The degree to which our estimates are off generally conforms to roughly the same proportions. If we were to examine a particular worker’s estimated task completion time to the actual completion time over the course of many tasks, we can determine the approximate factor to apply to his estimates to find the actual completion time.
The root cause of this predictability is the simple fact that humans are better at being precise than we are at being accurate when it comes to estimates. In other words, we’re quite good at approximating the relative size of a task, but we fail at determining the appropriate scale.
Take the chart below. Here we see an intentionally simplistic view of a worker’s estimated completion time versus their actual completion time.

At a glance, our worker appears to be a poor estimator, as he has underestimated each task. However, if we look at the data a little closer, we can see that on average, he was of by a factor of approximately 1.8. If we were to apply this factor to his estimates in advance we’d see a slightly different picture.

As you can see, by applying his average estimation scale factor to the figures we can calculate a much more accurate set of estimates. Of course, in practice, five data points will not provide a very accurate estimation scale factor, but by collecting this data over the course of several projects we can get a pretty good sense of this worker’s estimating characteristics.
Tracking this data manually would be cumbersome to say the least, but it’s something that a computer does very well. Given the proper tool, this data could be collected behind the scenes with little to no impact on workflow.
It just so happens that I am in the midst of building such a tool. For now, let me say that this will be a web-based, hosted, project management tool. I will be applying my many rants on the subject to creating not only a better tool, but a better process for project management. This will not be another to-do list manager, I promise you that.
Now that the cat is out of the bag, I will be posting regularly throughout the development of this tool and I will be craving your feedback. Many, many more details to come. Stay tuned.
