One of the most dreaded parts of long-term planning is the effort estimation process. How much work will it be to do the things we think we need to do?
When you find yourself in this situation, the most important thing to remember is that your goal is accuracy and getting close enough to the size of work, rather than precision, which requires detailed certainty about the small pieces that will make up the work overall.
To illustrate this, let me take you through a portion of my own yearly planning process. It starts bottom-up. Each subteam goes through their staffing and their desired project list, estimates the cost of the projects balanced against the staffing they have, and roughly sorts the projects into ‘the things we’re definitely trying to do’, ‘the things we might do if that other stuff goes faster than we expect or if we add people’, and ‘the things we want to do but probably won’t be able to get to’.
