At my very first job out of college,¹ the VP who led the division that I was part of invited me into his office (I think there was someone else from the team, but this is 34 years ago so who knows) and talked about a little game he had encountered about estimates. He gave us a list of 20 things to estimate with 95% confidence (the only one I remember was the weight of a 747), all given as a range. If we did it right, we would get 19 of the 20 correct. The point was to set the range large enough that you could be confident about the answer.

I kept that as a practice when I did freelancing work, always giving my estimates as a range rather than a single number. It would be nice if agile(ish) practices incorporated this in the estimation process.

⸻

1. Technically, my second job since I had a short temp job doing some cataloging work at a local used bookstore between leaving school and starting at that company.