@jbrains important thing is to not treat the estimates as promises. People recalibrate their estimates as they learn more. They like it.— clarke ching »» (@clarkeching) April 18, 2015
@jbrains back when I did real work, I promised every team I'd buy them ALL an expensive lunch if I EVER reacted badly when a task "overran"— clarke ching »» (@clarkeching) April 18, 2015
@jbrains and, because I always thanked them for their quick re-estimate, no matter if good news or bad, they were always honest.— clarke ching »» (@clarkeching) April 18, 2015
If you're willing to start acting like this starting now and the people around you are willing to start acting like this as well, then you have a chance of not failing horribly with small-item estimates (work needing around 1 month or less).