I saw a segment on 60 Minutes a while back where they interviewed a customer service executive for a company (I forget the industry) who admitted to intentionally designing the phone prompts to be difficult to navigate and often resulting in an endless loop.
Regarding those voice recognition programs, sometimes I’ve found that talking “jibberish” will get you to a live body quicker than speaking in clear, recognizable language (“I did not understand that, transferring to a customer service agent.”).
I always try to be nice when dealing with these folks. I’ve found that being polite, cordial, respectful, etc., has been worthwhile. Not CS/TS, but I was once in the process of obtaining bids/estimates for a rather large scale landscaping project, and one guy admitted to charging an “asshole tax.” So I see little upside to the converse approach.