A routine question will evoke a routine response. Thus, “How’s it going?” will generally get a “Fine, thanks,” or perhaps a “I can’t complain.” If the purpose of the question is merely to acknowledge an acquaintance briefly and move on, your purpose is served. This is the social function of language that the anthropologist Malinowski called “phatic communion,” which is nothing more than a brief and superficial verbal connection, the smallest of small talk. However, if you’d prefer a more substantial conversation, you’ll need to use a different question to evoke a different response. A deeper and more detailed conversation will certainly be less predictable and probably more interesting, and it will likely have the effect of enriching your relationship. 

Here are four suggestions for more evocative questions: 

  1. Ask questions that elicit detail. These are often “What?” questions. For example, “What did you finally decide about relocating?” or “What did you do on your trip to Mexico?” will usually stimulate detailed responses. Questions that don’t require detail, such as “How are your plans coming along?” and “How was your trip?” can be answered with a mere “Fine, thanks.” 
  2. Ask open questions that require more than a Yes or No. These are the “Wh” and “H” questions beginning with What, Why, Where, and How. These work better than “closed questions” that limit the response, such as “Did you like the movie?” Instead, “What did you like about the movie?” elicits a more interesting and detailed response. 
  3. Ask some questions that are a little bit surprising or “edgy.” These are not meant to put the person on the hot seat, or to make them uncomfortable, but to be stimulative and get a lively response instead of a routine response. “What’s the most exciting/ challenging thing that’s happening with you at this time?” is such an edgy question. (Predictable questions usually evoke predictable responses, such as “What did you learn in school today?” “Oh, not much.”)
  4. Consider using some “If …” questions such as “If you had the means to pursue your dream occupation, what would it be?” Or “If you could have dinner with a famous person, whom would you choose?” 

Such questions break out of the routine and add some fresh energy to the conversation. By the way, don’t ever ask your partner in conversation any question you yourself would not want to be asked. And be prepared to answer the very “If?” questions you ask the other when your partner says “Let me think about that for a minute. Meanwhile, you go first.”