Measuring progress on a project is deceptively difficult with any level of complexity. You’d think it is easy when comparing it to a simple task like knowing how far along you are in cooking a meal or running a 5K.

The difficulty comes into flavors:

1) Correctly estimating the total time for project and 2) Correctly estimating the proportion of time you’ve already completed

I’ve tried to use tools to help track this in the past but with little success due to a variety of factors. When I was working on a larger team (10 people rather than 2) it was difficult to get buy-in on the value of tracking this information and paying for the tool to do it.

Now that I’m part of a 2 person team and we’re having to evaluate whether it’s worth our time. Any time spent managing a project could also be spent working on it and moving closer to completion. But the real value in one of these tools is that it can track how good you are at estimating time by tracking your estimates and actual time spent on an item. If you know you always estimate 20% lower than your actual time then you can adjust for that in the future.

In our business, where we fixed-bid most projects, that knowledge could be pure gold.