Scott, the usual ways you learn any tool. Play with a test instance. Then read your logs, read the docs, take part in a community such as the one here, read some blogs, go to some user groups, buy some books, read the books. Listen to your users' requests and ask them "why?" rather than just doing what they ask
I'm assuming you mean JIRA admin so for a JIRA book, I like Practical JIRA Administration, O'Reilly because it has my name on it.
I have been a JIRA engineer for many years and I can honestly say that Matt's book is a clear, easy to read explanation of the core JIRA Admin concepts.
It's actually pretty small and easy to read: all stuff, no fluff.
I would recommend it to any aspiring JIRA admin.
The copy I read was written for JIRA 4.x IIRC, but most the core concepts have not changed.
Matt, has this ever been revised for newer JIRA versions?
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