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The key to it is looking for things that are personal and that you & "Bob" agree on, and then linking those to progressive points that will stick in his head later.
Talking about immigrants in the abstract, or making classic liberal points about the First Nations and slaves, doesn't go to the root of Bob's problem, which is insecurity based on fear. But linking immigration to his own family and to hard work, helps overcome the fear by reference to common values such as family and hard work.
Overcome the fear, and the rest will follow in its own good time.