The secret is to work with them, not against them. You as a programmer have a need. They as a sysadmin should be able to satisfy that need in a way that is acceptable to them. That usually means finding what the real need is, and setting up a process for it. For instance, blatant open access to one of the assets they control is not going to happen. But common tasks that you need to accomplish on that asset can have a process created.

I just want to second that the handwriting recognition in Windows 7 is, in my opinion and experience, quite nice. With absolutely no training on my HP TM2, it reads both my print and cursive with maybe a 1-letter error per sentence. But by far, the best part is their interactions after you've written something. Completely intuitive. Don't like a word? Draw a line through it, and it's gone. It got a letter wrong? Tap the word, and it explodes it out by letter. You can then insert, delete, or overwrite individual letters. Its only drawback is that it is dictionary based, leading to lots of corrections for words which, well, aren't really words.