some thoughts: 1) it seems that the accuracy of an estimate is inversely proportional the length of time for which it applies. In my experience engineers aren'

some thoughts: 1) it seems that the accuracy of an estimate is inversely proportional the length of time for which it applies. In my experience engineers aren't too bad at estimating if a task can plausibly fit into a two week sprint 2) I think the boss should be taking an active part in the estimation process, not just asking "how many hours/days". When I estimate with my teams I try to say "given x,y,z and the current state and that A,B,C blocks are not quite understood can this item reasonably be completed within our sprint" ..then we play poker / vote / comment etc. If the item isn't plausible for a sprint I'm (likeaboss) going back to the drawing board on that item to define it better and get it into more manageable pieces (consulting the team as needed) We're striving to make sure work items are defined well enough to be fairly confident they can be done in a short amount of time.