Organizations often doom projects to fail right from the start. Whether relatively small agile projects or massive megaprojects, a combination of poor estimating and poor understanding of estimates significantly contributes to failures. There are lots of clever tricks and complex calculations that enter the scene to deal with the potential of failure; some organizations even create a string of sacrificial “loss leader” projects to absorb the fallout from poor estimating practices. However, there is little writing that walks leaders through what estimates are and how to use them to establish project baselines and expectations – how to define success or failure in terms of the tolerances and techniques we prescribe to develop them.

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