I’ve done it many times and it really depends on the situation.  Once at a non-profit, it was simply the way everyone worked.  We were contractors and you could work whenever, wherever you wanted as long as you reached your goals for fundraising and event participants.  There were monthly scheduled meetings you needed to attend, but other than that…you were on your own.  With lots of support.

In a more traditional environment, I made the deal when I was hired.  I was fully prepared not to take the position if they didn’t allow me to work 80% time for 80% pay & benefits and if I couldn’t telecommute at least 1 day a week.  I was flexible as well, though.  If they really needed me in the office for a meeting either on my day off or on my telecommute day, I would be there…they didn’t abuse it, and I made sure I got my work done and on time.

Any other advice?