This was yet another fabulous talk from Ken “The” Power about estimating. For Ken though, if possible, the best way is to not estimate at all. Just trust that the team will do the work as fast as they can.
Unfortunately most teams have people asking “when” things will be done, so they need estimations. We’ve moved away from giving man hour estimations to using points, but that’s a whole other blog post.
But rather than give your story a single point estimation like “that’s 5 points”, give it a range. This adds a lot more richness and depth to your planning sessions, igniting much more interesting discussions. At the beginning of the project stories will be harder to estimate as you need more knowledge, therefore the ranges will be wider, as the projects move on they will become much smaller.
Thinking in range forces you to be considerate of Risk. Allows an upper and lower bound to your velocity, if you track the actual it should be in the middle. If you need to give an estimate use the value 2/3rd between the lower and upper bounds.
How do you do this in a planning poke session? You hold up two cards instead of one!