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How to assign a skill to an issue

For some of our issues we have only one team member who can do them. For those we assign this team member in Jira to the issue and let Portfolio for Jira schedule the issue based on that assignment. For other issues we have three team members with the same skill who can all do them. When we do scenarios for new set of issues (board) that we import into our Jira plan we would like Portfolio to schedule those second type of issues by assigning any one of the three team members whit the required skill who is available. How do we achieve this? Any help would be very much appreciated.

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