In my previous job I was asked to FTP our full client list (with financial information) to a third party acting on behalf of the company that had just acquired us. The IT Director of our new owners kicked up a hell of a stink and accused me of being 'unhelpful' because I insisted on the third party signing an NDA and installing AxCrypt so that I could encrypt the data for transmission. In the end I just said that if they insisted I send everying without encryption, I wanted it in writing with a disclaimer that I was acting on their instructions and they would assume responsibility for any possible liabilities arising with respect to UK Data Protection Laws.
By the time the IT Director had deliberated the point, the third party (who fully appreciated my position) had sent me a stock NDA, installed AXCrypt and we'd completed the transfer.