I have a couple of standard questions that I use when talking with people. One I use especially when talking with timid young people. I ask, “Tell me five things that have happened this week,” or some variety of the question. The key is to have a question with numbers and that can not be answered by “Yes” or “No.” That often gets people talking.
A second question that I like is to creat a positive response. It works well with people (pastors or missionaries?) who tend to be discouraged or negative. I say, “Tell me what exciting things are happening in your ministry. What is God doing that you are most happy about?” I really like this because it immediately puts the conversation into a positive uplifting conversation.
Give it a try. One other question I use is “What’s new?” Usually the answer is, “Nothing.” But I keep asking until they say something.