Recently, I had the opportunity to look at a set of user stories on an upcoming project and apply a high level estimate to each. These estimates were going to provide a starting point for determining project timeline and schedule. Every time I’m presented with a request for estimation, I shiver a little because I’m so bad at it. As I understand it, I’m not alone in this weakness. I have found, however, that the more requirements that can be defined and the more detail that can be described for each, the more accurate a timeline can be established.