[chrisma0]

I consider task estimation as part of Sprint Planning an interesting domain, as multiple people in a team with potentially vastly different experience levels and skills are involved.

MacIver points out "if you’re doing sprint planning, and you absolutely have to do it through estimating individual tasks", give three point estimates a try. Here is the Wiki entry for that: https://en.wikipedia.org/wiki/Three-point_estimation

I guess explicitly recording the best-case and worst-case estimates might be interesting.

[kaoD]

I don't think a PERT distribution accurately describes software estimates due to the upper tail being potentially infinite.

See figure 1-3 here for my mental model: https://www.microsoftpressstore.com/articles/article.aspx?p=...

(Pretty sure if this distribution has a name but I can't remember it)

[ranguna]

One issue that could arise is that delivery managers could take the worst case estimations as an absolute truth and would think that no task could go over the worst case scenarios. I'm sure there would be a few tasks that would go over and would break planning.

But it could work if people are aware that even worst case estimates are not absolute truths and could go over the limit some times.