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Journal Journal: Executive Management vs IT. Suggestions to resolve the disconnect?

I work for a Medium Sized law firm as a Sysadmin/Network Engineer and as most people saddled with this type of work, I have an aging undocumented infrastructure that creates more labor than my budget gives me the ability to standardize. I finally caused enough of a scene that I am allowed to write up a proposal to simply compare COO vs ROI, however even in my first draft document I realize I am being too technical for them to understand what I am saying. How have my peers handled this type of disconnect between Execs/Non-IT Management? I am looking for specific case studies in layman's terms that address these overarching types of "Information Technology Governance" problems. It would be doubly helpful if they were specific to Law Firms.

The trouble with a lot of self-made men is that they worship their creator.