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I haven't had a conflict about sending proprietary samples. But if I did, I
might take the help file, cut it down to a few representative sections, and
search and replace sensitive material (including all identifying info). Of
course, this may not be possible with all help systems. But it seems like
one way to go.
I also got my first help writing job by showing my sample "African Violets"
help, which I had done completely on my own. I had to show that I could
design a help system that used the technology available then; I hadn't had a
paying job that enabled me to create such a help system, so I created one on
a topic that interested me. I got the job, too.