When estimating tasks, how does one break from the grip of Hofstadter's law?
Hofstadter's law is the observation that “It always takes longer than you expect, even when you take into account Hofstadter's Law.” In other words, time estimates for how long anything will take to accomplish always fall short of the actual time required -- even when the time allotment is increased to compensate for ...
It's called the planning fallacy, and it means that a sense of optimism causes people to underestimate how long it will take them to complete a task. In other words, we're too busy thinking of the best-case scenario to consider how the project could go wrong or where we might hit a snag and need more time.
If you can politically: Estimate in small chunks, work in small iterations, and focus attention on what caused the deviation from the estimate to make the next estimate better.
One of the major causes of bad estimates in my experience is the lack of experience actually using the architecture planned for the project. By adjusting the estimates as things become more concrete and clear the estimates get better over time.
The other major cause of bad estimates is bogus estimates. Estimates kept artificially low to win a bid. The only way a consulting firm can break that cycle is give good estimates and win enough projects and deliver on the estimates to earn a reputation that they hit their estimates. Enough clients will respect that to make a reasonable business out of it, but building that up will be hard.
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