Look up books on the topic of "Operation, Administration, Management and Troubleshooting X" where X is the technology you are using. O'Riley tend to have Operat

Look up books on the topic of "Operation, Administration, Management and Troubleshooting X" where X is the technology you are using. O'Riley tend to have Operation books on different technologies. I highly recommend as a start Kyle Rankin's DevOps Troubleshooting Linux Best Practices. DO/Linode tutorials are good for setting up X but may not be necessarily good for troubleshooting. After being in service side of IT infrastructure for over a decade, what I found important is the breadth (generalist) and not depth (specialist) of knowledge. Surround your support person with appropriate resources (specialists, books, trainings, google). The key to success is not what he knows but where he looks to find what he needs. ed: added more info