You don't have to, but you might be seen as rude or odd - although people might understand if you're a foreigner. At a party where you don't know people? I wouldn't, unless presented by a mutual friend. Usually I just greet whoever comes forward to greet me - I normally don't initiate the kissing.
The plumber, no. No service people/workers. Family, friends, coworkers, people you are presented to, etc.
Your CEO?
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