Another Two Sides to Estimation

There are many ways to look at the issue of estimation. Everyone in the business of software development has had experience with wanting estimates, being asked for estimates, or both. That experience frames how they look at the issue. A considerable share of those experiences have been painful. I dare say that everyone in the business has had some painful experiences around estimation, and the painful ones seem to stick in our memory more vividly than the benign ones.

What makes these experiences so painful? Again, the causes are legion. One frequent contributor is well illustrated by a story my older brother taught me as a child.