To assign tasks we are doing iteration planning meetings (IPMs). In those, we specify which tasks I have to do next. The tracking of those tasks is done in a kanban board.

Then I have to estimate how much time I think they are going to take. The time units are half day of work. That means that 2 units are a full day of work (8 hours). The time units are not divisible. And an estimation can’t be 0 time units. That estimation is based on 3 points of view:

  • Being optimistic.
  • Being realistic.
  • Being pessimistic.

I am noticing that maybe I am being pessimistic by default. Optimistic, realistic and pessimistic seem subjective thoughts. I can’t estimate with subjective thoughts, they are unreliable. So I have to find a more objective way of thinking about it:

  • To achieve that task, what are the steps I have to take?
  • Do I have some experience in some of the steps? How much time did they take?
  • Optimistic: Everything goes really smooth, there are no interruptions, full focus on the task…
  • Realistic: Considering some interruptions, some moments when one can’t focus properly, maybe I missed one or two steps to complete the task…
  • Pessimistic: I got my assumptions wrong. There are missed steps to complete the task that I did not think of. I am being interrupted often. I can’t focus on the task. I will dedicate out-of-work time to keep up…

The problem of thinking pessimistically that way is that my estimations are very exaggerated. I had to think about it from other point of view: It should not take more than X time to do it. Thinking of it that way made me value the time I was spending in a task.

On the other hand. If I have never done anything similar enough to the step I’m trying to estimate, How am I supposed to know the time is going to take to do it?

I feel really uncomfortable estimating, that means I need to improve on it.