Disclaimer: I work for the vendor of the mentioned below add on.
For JIRA Server one might try using Agile Poker Enterprise for JIRA add-on for doing interactive estimation session (using Planning Poker technique). It also allows to specify T-shirt sizes (S, M, L, etc) as estimation choices and map them to the numerical value (2, 3, 5, etc) while saving final estimate to the issue's story points.
Feel free to ping me at firstname.lastname@example.org if you have any further questions on that matter.
Piotr Stefaniak / Spartez Developer
You could use your t-shirt sizes as a first estimate for the complexity/size of your issues.
But Greenhopper needs numbers (hours/story points/...) to calculate things.
I would recommond you to use T-shirt sizes (in a custom field) to quickly triage your issues and then do a poker planning estimation by story points for the top 25% of your product backlog (Or even an indepth technical estimation in hours if you want).
These story points (or hours) can then be used within Greenhopper.
We have a default setup, so the custom field for Story points is an integer and it can't be changed via configuration.
Do I have to create a new custom field with Select list field type? How will GH plugin know which value is more time consuming/complex?
Is there a tutotial or some guide how to setup JIRA 5 and GH 5.10.5 to estimate in T-shirt sizes?
I'm not sure there's actually a question here any more, although I admit I must have been slacking and missed the second comment.
The answer to the original question (which isn't really much good because the question didn't explain what was being done) is "yes, use a custom field with whatever names you need",
Then the original poster has siad that they're using Story Points for it, so the answer is "no, you have to use numbers for Story Points because Story Points are by their nature, quantitative, and GH needs them to be numbers"
You're taking the better approach of using a well labelled field, but that's never going to translate to numbers on it's own, you'll need a bit of code that will read it, turn the points into numbers and then store that in the Story Points field.
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