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Where I work we don't estimate in time, we estimate in points. Points are intended to represent engineering's view of the relatively complexity and uncertainty of a given story.

Pivotal Tracker then looks at story delivery over the past 3 weeks and gives a simple average: velocity. You can then look forward to see approximately when future stories will be completed. You can also see a volatility measurement, which characterises how much velocity is fluctuating.

Our horizon is deliberately short, because we move very quickly.

Nevertheless, it has a simple advantage: it is based on the true and most recent data of the exact project you are estimating.

Other estimation techniques are useful in other situations, but simply being able to say "those are the actual numbers for this project this month" is enormously powerful. There's no fudging. The numbers are right there in black and white.

It usually takes a little while for people new to this approach to accept that velocity is not a target; it's a measurement only. It's a unitless measurement that is only meaningful within a single project, operating at a floating exchange rate with calendar days.

One last thing that helps, as others have pointed out. Break down your estimation tasks into smaller units. Never accept the small headline that hides a big feature. Continuously look for seams to break big stories into small stories. When the pointing begins, summarise aloud with fellow engineers a rough idea of what will need to be done.

Psychologists call this the "unpacking effect", and I suspect that it's responsible for most of the estimation-increasing power discovered in more fully-dressed estimation techniques like PERT, parametric estimation tools or even good old fashioned checklists.

(I was working on an estimation tool for a while, so this subject is dear to my heart).




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