There are a number of communication guidelines that should be considered when dialoguing with a Jewish friend or family member.
First, learn if the individual is Orthodox, Conservative, or Reform. Orthodox Jews are ultra-observant. In fact, you will probably be able to discern if someone is orthodox before you even ask a single question. However, by contrast, conservative and reform Jews are more difficult to identify. Remember, conservative Jews are semi-observant, believing in the Hebrew Scriptures. By contrast, reform Jews are non-observant, and are often very secular. Asking appropriate questions can help to discern how an individual would identify themselves.
Second, for Orthodox and Conservative Jews, discuss the meaning of Hebrew messianic prophecy, because they believe it’s inspired. We have considered many of these in an earlier article (see “Jesus and Messianic Prophecy”). Michael Brown’s book Answering Jewish Objections to Jesus: Volume Three is an excellent, seeker-sensitive book on the subject as well.
Third, with reform Jews, determine another underlying worldview such as atheism, agnosticism, or post-modernism. Dean Halverson writes, “Reform Judaism began in Germany in the eighteenth century at the time of the Enlightenment, or Haskalah. It sought to modernize what were considered outmoded ways of thinking and doing and to thus prevent the increasing assimilation of German Jewry. Reform Judaism emphasizes ethics and the precepts of the prophets.” Judaism is often called the religion of the deed—not the creed. Thus be prepared to discuss various worldviews, rather than biblical Judaism—especially with those who hold to a reform background.
Fourth, with all Jewish friends and family, be prepared to discuss church atrocities, which are prevalent. Most of our Jewish friends have been raised on the stories of “Christian” atrocities throughout history, and simply assume that Christianity is, therefore, an evil religion.
Fifth, explain that Christianity is not a new religion but the fulfillment of an old one. Often demonstrating the Jewishness of Jesus and the apostles can help to make this case. Also demonstrating the consistency and unity of the New Testament with the Hebrew Scriptures is helpful.
Sixth, make sure not to use language that is stumbling to a Jewish person. For instance, do not use the term “Old Testament.” This makes it seem as though the Hebrew Scriptures are old, and New Testament has replaced it. Instead, use “Hebrew Scriptures” or “Hebrew Bible.” Likewise, do not use the term “Jew.” While Jewish people are free to use this term for themselves, it can sound pejorative coming from a Gentile. Substitute this word with “Jewish person.” While this is a bit more cumbersome, it does much to help in communication.
 Halverson, Dean C. The Compact Guide to World Religions. Minneapolis, MN: Bethany House, 1996. 123.