There's no question that early adopters enter into uncharted territory. But there's an even bigger danger: Despite making the best decisions at the time, early adopters face an uncertain future.

Proskauer executives had to draft user policies about an entirely new computing platform, choose fast-evolving iPad apps to handle day-to-day heavy lifting, and rely on emerging mobile management software.

But the IS department's user policy manual had to go further to advise lawyers to stay clear of cloud-based services despite the fact that many apps such as Docs to Go and Quickoffice let users tap into cloud-storage services like Dropbox. Proskauer lawyers, Collingwood says, shouldn't be using Dropbox to move documents from their desktop to the iPad or vice-versa.

"It has to do with confidentiality of information," he says. With Dropbox, "you're leaving it up to the individual to go to the cloud and purge those documents."