Personally I (as a Scrum Master) believe that people are over tools. Having the tools dictate what you should and should not do takes away social and personal responsibilities. Team members will start thinking that the tool will solve all problems and over time the team members will degenerate into tools slaves instead of highly motivated and responsible members.
I am from Scandinavia so I might be extremely biased towards individual freedom and responsibility and accountability over rules, razzia and tool enforced methods.
Reading through many of the questions and answers here it does seem that especially Asia (or people managing people from Asia) is struck by the "more rules"-concept.
So my answer is: More training. Agile Scrum is 200% about encouraging the team members to take personal stake in what they are doing rather than being treated as cattle being pushed arounf with yet another new stick called "Scrum in JiraAgile".
Encourage the team, talk about the values of Agile Scrum: Courage, Openness, Respect, Focus, Commitment
In regards to get the estimates right I suggest taking a good look at Commitment, Respect and Openness in regards to getting the sprints right.
Also do look into having a Definition of Ready and Definition of Done for the team as this will get the team to talk about exactly what the quality goals for all work is and the goal for good story preparation is.
I hope you can use this for something.
Why don't you make the field required on the Open -> In Progress transition?
They will still be able to add the stories to a sprint but they will not be able to start them untill a value is filled in for the Story Points?
But as Kim says : it's really a team issue. Ask them why they aren't doing it? Don't they see the advantages? Is it too much work? (This is Peter the Scrum Master speaking now)
Maybe you could organize a meeting each sprint with as your only goal : give all stories a story point estimation, you can use planning poker do this more easily.
I get where you're going with that... but i don't think it will work.
The idea of Sprinting means your sprint team members have commited to completing work/stories by the end of the sprint. The story points measure the teams estimate of that body of work. If there's no estimate, there can be no commitment.... so i don't want stories to be dragged into the sprint without that estimate process happening. I have several teams using JIRA/Greenhopper, so it hard to enforce right now. Any idea's ... (other than additional training!!) I'd just like to enforce it via the tool if possible.
That would involve a workflow change to add another status that can be transitioned to because Open -> In Progress is already in a sprint.
If the estimate is set to be required on story entry it would completely hamper entry of anything to the project, or get the project estimate count skewed completely due to lots of bogus or zero estimates being entered.
So it can be done but will have consequences.
As I understand the question the problem at hand is that sprints are created and commited to with unestimated issues. This is definitely a team issue.
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