In my current job, I upset those people who think that using Web 2.0 to talk with employees and journalists is the equivalent of turning the comms function into the online version of Animal House (…. I would still like the Toga Party though).
In a job I had years ago, it happened when I was trying to convince management of the importance of treating CSR as a core component of their message and not like a pet project.
Hearing Seth Godin speak at TED about the importance of challenging the status quo was immensely refreshing.