We are using MS Active Directory and JIRA 6.0.7. The rationale behind this request is "my boss needs to sign off a request for access to system", "my boss needs to say its ok that i need that new phone", etc.
If it costs you more to implement and maintain then it will ever cost them to do it manually it doesn't really work out in my opinion. But if you really need it then I wish you good luck on finding a solution. You could think about doing something with user properties, or defining a different workflow for each departement (and adding the boss in a project role for example).
What would the exact reason be to assign this to "your boss". Would this be because they get notified they have an issue assigned to them, and act accordingly? In that case you could consider using @mentions to notify your boss instead. Would this be so he/she sees the issue show up in their personal queue? There are several post functions available which can assign an issue to an entity. I personally think the "Copy Value From Field to Field" would serve your purpose best. This does however require you to add a custom user field in which the reporter of the issue selects their boss. With the post function, you can copy the custom field user into the assignee field at the transition at which it become relevant for the boss to sign off on the request.
I am not aware of any methods to automatically determine the boss of any given user.
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