I'm a lawyer, not IT, so my answer may not be all that useful. That said, there are two major hurdles at law firms. First, the management structure is ridicul

I'm a lawyer, not IT, so my answer may not be all that useful. That said, there are two major hurdles at law firms. First, the management structure is ridiculously flat, and the people running the show are usually the most senior attorneys. Just so happens, those are the people least likely to be using the technology. Second, most of our software is custom/old-as-dirt. Upgrades require direct participation of vendors who have us over a barrel, and for that reason, no incentive to move quickly. It's an extremely painful/slow/expensive process. IMHO - Big Law is due for disruption in this area. NetDocuments appears to be making some headway. Unfortunately, lawyers and, thus, law firms, are extraordinarily risk averse. Startups will have difficulty capturing this market.