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I have some issues that multiple people work on at the same time, am I able to assign this one issue to multiple people? Would I have to create multiple instances of the same issue to assign it.
You have multiple options
1- Create subtasks for each of people in the task
2- Create a multi-user picker custom field and use it for these cases
3- Break down the main issue into two separate and related issue and assign each one separately
The order of my list is my preference for these situations.
If I have an operational, day to day task and want to assign it to several people on a team, is there an easy way to do this? This is a pretty common think to do, I hope it isn't as complicated as it sounds... I'm coming from MS Project and it's pretty simple there, is there an equivalent here?
Welcome to the Atlassian Community!
You should never assign an issue to many people, in real life, it will break things, you'll miss stuff. It's a terrible thing to do with an issue.
But that from is the definition of assignee in Jira - the assignee is the person who is currently supposed to be getting the issue dealt with - that can never be a group or team.
But it's never a bad thing to have a group or team involved in an issue so that when the assignee isn't around or is not working on it, you have other people you can ask and even re-assign to.
@Ansar Rezaei already gave you some options, but I would add:
No i'm not advocating any solution specifically for pair programming with TDD. I did not read that into Samantha's post. Admittedly, that underlying detail might apply here but it is just as likely that it does not.
What I was attempting to convey was:
It is worth mentioning that you can certainly get around 'assigning an issue to a team/group', but (again IMO) it is messy and error prone.
Regarding your last question, we are not using pair programming w/ TDD at my workplace thus any answer I give would lack experience so will abstain. However, you might find this Community article of interest - Managing-Assignee-when-you-do-Pair-Programming