This is an old article from Cory Doctorow, but you should read it if you want to successfully implement KM (Knowledge Management) in your firm.  Though Cory is talking on the problems of promulgating reliable metadata (“data about data”) on the web at large, I think his observations are true in small organizations as well.  Cory gives seven insurmountable obstacles that will keep us from reaching “meta-utopia.”  In a law firm setting, these are the ones that seem most likely to torpedo a successful implementation of KM:

People are lazy

You and me are engaged in the incredibly serious business of creating information. Here in the Info-Ivory-Tower, we understand the importance of creating and maintaining excellent metadata for our information.

But info-civilians are remarkably cavalier about their information. Your clueless aunt sends you email with no subject line, half the pages on Geocities are called "Please title this page" and your boss stores all of his files on his desktop with helpful titles like "UNTITLED.DOC."

This laziness is bottomless. No amount of ease-of-use will end it. To understand the true depths of meta-laziness, download ten random MP3 files from Napster. Chances are, at least one will have no title, artist or track information -- this despite the fact that adding in this info merely requires clicking the "Fetch Track Info from CDDB" button on every MP3-ripping application.

Short of breaking fingers or sending out squads of vengeful info-ninjas to add metadata to the average user's files, we're never gonna get there.

People are stupid

Even when there's a positive benefit to creating good metadata, people steadfastly refuse to exercise care and diligence in their metadata creation.

Take eBay: every seller there has a damned good reason for double-checking their listings for typos and misspellings. Try searching for "plam" on eBay. Right now, that turns up nine typoed listings for "Plam Pilots." Misspelled listings don't show up in correctly-spelled searches and hence garner fewer bids and lower sale-prices. You can almost always get a bargain on a Plam Pilot at eBay.

The fine (and gross) points of literacy -- spelling, punctuation, grammar -- elude the vast majority of the Internet's users. To believe that J. Random Users will suddenly and en masse learn to spell and punctuate -- let alone accurately categorize their information according to whatever hierarchy they're supposed to be using -- is self-delusion of the first water.