Here are 7 estimation blunders and also how you could fix them. Fair warning: in most cases, there are no easy answers.
1. Estimates because “We have to”
Estimating for the sake of estimating makes no sense. It will not bring the predictability that people seek in their plans. It will only result in disappointments, especially when the estimates are leading the conversation. When it is more about “When will it be ready?” than “What have we learned?”
2. Neglecting different estimation opinions
Arguably the greatest merit of estimating is that teams can have a conversation about the work at hand. Whenever someone thinks an item is small while another says it’s extra large, this should trigger a discussion.
3. One estimator to rule them all
When you work as a team, everyone who has a part in the work also should be part of the estimation. Regardless of the seniority or expertise of a person, they may have important insights that help everyone to paint the picture.
4. Estimating takes forever
Unless the work is clear-cut, it isn’t realistic to assume everyone will be on the same page. Now, whenever I see this occur, I advise the team to seek consent instead. Instead of having everyone agree on an estimate, you can also ask for permission to have an estimate of ‘M’ from the person that thinks it’s an ‘S’.
5. Estimates need to be “correct”
Estimates are rough calculations. As rough calculations, they ARE correct. As they reflect the notion of the members of a team at a certain point with the information they have at that moment. Therefore, the way to solve this issue is to simply treat estimates as rough calculations and accept you learn while you work on the item.
6. Estimates are turned into commitments
Isn’t your team allowed to push back? Then this surely can’t be the only thing holding the team back. It is a clear sign that the team can’t be effective because of command and control constraints. These are organizational impediments that should be resolved.
7. Others do the estimation
You should leave the estimation to the people who do the work. Sadly, real life isn’t this simple.
Canary in the coal mine
The way the team and the organization handle estimation is like a canary in a coal mine. The way estimation is done and used can quickly answer some interesting questions:
how is the purpose of estimation understood?
how much is complex work understood?
how well does the team collaborate?
what are the power dynamics in a team?
how self-organizing are the teams?
There’s so much more to it than a number. It’s all about having conversations and the power dynamics too.
I would also add estimating based on who is doing the work (Individualizing vs Team Based). I am amazed how often I have heard comments like "it is a 3 if x does it but a 5 if y does it" The idea of individualized estimates as opposed to team based estimates seems to keep recurring despite completion of a PBI/Feature etc requiring more than one person.