[ChrisCinelli]

There are ways to get better at estimates. And a proper process will help you to do it. Unfortunately most of the orgs do not do it.

1) We know that "People are bad at estimates". That is why the estimate should come from the team (not one person in the team). Most of the orgs that I know do not do this. And to be honest they are not set up to do it because people in a team do not have overlapping skills. Ideally you have a team where people can take other people jobs (to a certain degree). You can then, during grooming, play "poker scrum" to estimate (where it is harder for people to cheat following what the lead person says). It is ok for somebody to say "I have no idea". The AVERAGE (not the MODE) is used for the estimation. If the items are more than 2 card apart have the 2 people at the extreme say why they think they think it takes the little amount of points and the other person why they think should take the large number of points.

2) If it is hard to agree on the estimation, the item probably needs to have a "spike" where more assessment or design is done in order to make clear what need to be done. In my team we also agree that a story has more than a certain number of points, we may say that it is too big and we have to break it down.

3) During retrospective or a specific meeting we have the team look at the time that an item really took and when it was more than 2 card off, try to understand what was under or over estimated.

Usually after about 5 cycles, people start developing a sense of what the right amount of story point should be for a story.

If you are always left by yourself at estimates and you never properly scope the task before and reflect on the variance afterward, it will be very hard to become good at estimations.