How to Estimate a “Big” User Story Accurately

Eiki Takeuchi
Beyond Agile Leadership
9 min readJun 21, 2024

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Estimation is one of the biggest challenges in software development since our business circumstances and technologies change rapidly. Steve McConnell, the author of the Cone of Uncertainty, says no project has the same requirements, same people, same business context, same technology, and same constraints. It makes the estimation difficult.

However, since software development is a business and there are always investors who care about ROI (Return On Investment), you must estimate it as accurately as possible. I’ve seen some people arguing that software development must not be estimated because it’s impossible. However, it must be so to be accountable. While it’s true that estimation is hard and is (almost) impossible to achieve 100% accuracy, you can improve its accuracy with techniques and best practices.

In Agile, estimation is conducted based on a user story, a core deliverable to customers. When I started as an Agile coach, my estimation was too inaccurate because I didn’t understand the importance of a user story and estimation techniques. To compensate for the mistake, my team and I needed to work overtime, losing the trust of team members and stakeholders.

A user story tends to be too large since it is a core deliverable, and stakeholders commonly demand more than the capacity. In this article, I focused on…

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Eiki Takeuchi
Beyond Agile Leadership

I'm Eiki Takeuchi. I work as a Scrum Master/Agile coach. I regularly write about Scrum, Agile, and leadership on Medium. X: https://x.com/eiki234