I&#x27;ve never experienced estimation improving over time in an Agile process. In fact, since short estimation cycles are just as susceptible to political games as longer cycles, and this dominates the whole process in any organization, the length of the estimation cycle really has nothing to do with the estimation issue.<p>But, what shorter estimation cycles are responsible for is a decoupling of the overall big picture progress from the immediate tasks being prioritized. This often leads to sprints that are well scoped, and everything in the sprint gets completed close to on time (at least as close as in longer work cycles, but not usually any closer), but, <i>crucially</i> all of the work has to be scrapped because the whole sprint, <i>conceptually</i>, was not right. In my experience, this happens maybe 1&#x2F;5 of the time in Agile exactly in ways that would be prevented with longer-term planning.<p>It&#x27;s very similar to the classical fractal effects of measuring the coast of Britain. By refining your ruler, you merely <i>think</i> you&#x27;re being more accurate, and a lot of people are doing a lot of performative managerial crap for the sake of the Scrum performance, like a ritual. It <i>feels</i> like you are estimating better, but really because the whole meta-level <i>concept</i> you are working on isn&#x27;t guided by longer-term thinking, you end up having so much round off error, added up over more and more cycles, that the overall waste is colossally greater than systems that involve some more significant longer-term pre-planning and which work on variable cycle lengths instead of a cookie-cutter, one-size-fits-all approach (which is the core philosophy of Agile, though people try to obfuscate this fact by No True Scotsman-ing it with the Agile Principles).<p>I also can&#x27;t miss the opportunity to point out this great article on the political games we play during estimation: &lt; <a href="http:&#x2F;&#x2F;research.cs.queensu.ca&#x2F;home&#x2F;ahmed&#x2F;home&#x2F;teaching&#x2F;CISC322&#x2F;F09&#x2F;files&#x2F;EstimatingGames.pdf" rel="nofollow">http:&#x2F;&#x2F;research.cs.queensu.ca&#x2F;home&#x2F;ahmed&#x2F;home&#x2F;teaching&#x2F;CISC3...</a> &gt;