Got onto Mike Cottmeyer’s article ‘The Real Reason We Estimate’ via XP Injection and couldn’t agree more. We often do underestimate, and reason is not that estimation as activity is broken, but that oracles we make our estimation upon are not informative enough.
Instead of skipping estimation, we should analyse why it’s failing and improve those areas.
Estimating is about creating a shared understanding of the requirements, and a shared understanding of the solution. When teams have problems estimating, its almost never an estimating problem, it’s a shared understanding problem.
Shared understanding problems can result from any number of organizational dysfunction’s. Some of the most common are on the product side… insufficient business involvement, insufficient understanding of the business problem
The other big shared understanding problem comes from technical debt… poor architecture, quality problems, or even just teams that are unfamiliar with the code base
You really should read the article in full