[throwaway9191aa]

Our team had so many planning poker sessions where we spent 12 people * 2 dev hours trying to figure out whether stories were a 2 or a 3, management finally said it is always a 3. We were literally spending more aggregate time trying to decide effort, than the actual effort it took to complete these tasks.

2 and 3 are equal. 5 and 8 are equal. The question is simply "Is this a couple days, the whole week, or the whole sprint?".

[dsr_]

The only reasonable estimates, ever:

+ That's trivial, it will be ready for testing before lunch.

+ I know how to do that, should be ready tomorrow/next day.

+ I can see how to do that but there are lots of other constraints - at least a week, might be more.

+ It's a big project, needs more planning and specification before it becomes a series of estimable tasks. Let's do that.

+ That breaks other things we care about. We need to prioritize and be ready for rework.

If you want, you can call these small, medium and large.

[politician]

I completely agree with these levels, but disagree with mapping them to “small, medium, and large.” That’s a lossy compression if you will, and the heart of the problem. A shorthand might start with good intentions, but rapidly is muddied by conflicting interests.