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This reminds me of the "extreme programming" planning technique: you estimate work by chopping it up into tasks and figuring out how long they would take in "ideal days" (that is if everything goes perfectly) . Then you see how many "ideal days" worth of tasks you managed to deliver last month (for instance) and multiply your estimate by the ratio actual days/ideal days.

This method works reasonably well but people can be quite resistant to facing up to the consequences of how long things actually take. It strikes me that this is a pretty good template for de-biasing in general: use frequent feedback of reality to adjust your priors.