Better Answers Come From Better Questions

Of course, the tried and true way of directly getting deeper with people is to ask better questions. The simple truth is that most questions we use are surface level, and thus will only return surface-level responses. Here are a few guidelines for more piercing questions that will create more fertile ground for real substance: ask open-ended questions (don’t ask for facts, ask for the analysis and reaction associated with the facts), go beyond assumptions (what are you missing in your own analysis?), get all sides of the story (the more perspectives the better), use follow-up questions (don’t interject your own thoughts), get comfortable with dead air and in fact utilize it, and encourage people to come up with their own insights (so how did that change your opinion on things?).

Ask Better Questions

Finally, when it comes to going deeper, there’s one certain way to do it: by wielding questions as shovels.
Unfortunately, most questions we use just don’t get anywhere. They’re more of hammers and saws, which are not so well-suited for digging deeper. Some of them are made lazily, which prompts lazy answers in return. Others are plain confusing or meandering and without a clear purpose. Most of them aren’t geared at looking beneath the surface and understanding people.
Good questions help both parties develop deeper communication. Well-constructed inquiries can prompt a respondent to find new ways to think about their situations, which strengthens trust and keeps communication fresh. Thankfully, asking good questions is a practice that’s completely within your power.
Recall in the beginning of the book we discussed researcher Arthur Aron’s 1997 study on personal questions fostering feelings of closeness. Although the questions were not offensively intrusive, they were more than just small talk (“Would you like to be famous and how?” “Do you have a secret hunch about how you will die?” “What is your most terrible memory?” “How do you feel about your relationship with your mother?”).
Aron’s findings were clear: going more deeply or intensely in our communications can create positive results far more swiftly than one might think. Coming up with effective questions isn’t necessarily a reflexive act that we can do on the fly. To elicit more revealing answers that build depth and improve intimate relationships, here are six strategies that can be of great help in digging deep and learning about people.
These are most definitely not small-talk questions.

  1. Ask open-ended questions. Questions that require only yes or no answers will usually produce nothing more than yes or no answers. If the question contains no prompt for the responder to elaborate, there’s a very good chance they won’t.
    Open-ended questions, though, can spark discussions and bring up new, revelatory understandings that binary questions don’t encourage. For example, instead of asking, “Are you satisfied with your relationship with your mother?” you could ask, “Why is your relationship with your mother the way it is? How did it get that way?”
    These types of questions always seek to find reasons, stories, emotions, and patterns of thought. They are not asking for simple information in the form of facts. They are looking for the analysis and reaction before and after the fact.
  2. Get behind assumptions. We all operate through our own personal experiences, knowledge, and assumptions—you know what you know. Good communication involves understanding someone else’s beliefs. When they speak about issues that are unfamiliar to us, we ask them to explain what they mean, what they believe, or what assumptions they bring to the situation.
    Well-worded questions can bridge that gap: “How did you come to that conclusion?” “What makes this particular situation different from normal?” “What gave you this idea?” “What’s the story behind your belief?” When you sense a gap between what your partner is saying and what you’re familiar with, that’s the time to get clarity on what they’re basing their statements on. This is a prime mindset to learn more about the world and people other than yourself. After all, you can’t assume that only your assumptions and beliefs are reasonable—everyone’s are to some degree. So what is it that you are missing?
  3. Get all sides of the story. There are very few situations in life that are uncomplicated, cut-and-dried, or black and white. No matter how strongly someone feels about their particular viewpoint, there’s always more than one side to a given story. By getting as much information as we possibly can about a certain topic, we delve deeper and understand more about the total nature of a situation, problem, or event.
    This is often a case of not shutting out opinions or beliefs that might threaten or offend us, which in this day can be very difficult to do. But a responsibly asked question will help get a better picture of the greater context of things and will allow us to understand matters beyond our own limited view. “Is there another perspective on this situation?” “What are some of the things someone who disagrees with you would say?” “What would happen if someone did this differently?”
    In general, don’t be satisfied that you’ve gotten absolutely every fact of a certain matter to make an informed assumption.
  4. Ask follow-up questions. When we’re trying to get close to someone, a lot of the questions we may ask of them don’t have easy answers. In fact, if we were writing them out, they’d probably be more like two- or three-part questions with room to elaborate.
    In personal interactions, we can emulate that depth—and show the strength of our focus—by asking follow-up questions. But they don’t have to come immediately after your partner’s answered. One author (me) suggests seeing how many questions you can ask in a row without offering any comment of your own, so you can allow your partner to expand their response and keep digging deeper.
    It’s very important not to sound too much like a journalist or an inquisitor when asking follow-up questions. Instead, try to link your respondent’s answers to things they’ve already discussed: “What you just mentioned about not fully understanding computer technology reminds me of what you said about not doing well in school. How do those relate?” or “How did that breakup affect your views on relationships?”
    Good follow-up questions will make you sound invested in your partner’s response—and it may take a while for you to get to the answers you both need to know. But that’s more time spent communicating.
  5. Get comfortable with “dead air.” People tend to be scared to death of “awkward silences”—those moments in conversation when there’s a pregnant pause and nobody says anything. We tend to misinterpret these silences as a sign that either we or our partner has run out of things to say. Sometimes that’s true. But sometimes, it’s someone trying to gauge you and subtly seek permission to keep talking.
    Thus, silence can work in communication’s favor—when you’re at ease with silence and don’t rush to fill it yourself with inane chatter, you’ll be prompting people to speak more and more. Think of it as seeing if moments of silence can help them generate their own, new thoughts and allow the conversation to get to a deeper level. This is perhaps the easiest part of digging deeper; give people the space to do it for themselves instead of at your asking.
  6. Encourage your partner to come up with their own insights. The best kinds of question-and-answer sessions aren’t just one way, with one person providing insight and information to the other. It’s always best—and far more conducive to good communication—when everyone’s learning new things.
    Questions that encourage self-discovery are, without exception, far more productive than questions that originate from a specific point of view. “What did you learn from that experience navigating the Amazon River? What do you think it added to your life?” Or perhaps “What would you want to say to your father if he were still alive?”
    Like all questions, those intended to promote self-discovery need to be carefully considered. You never want to sound like you’re on an inquisition, and it’s easy to fall into that trap without trying. Especially with interpersonal relationships, you need to strike that balance of getting information while being supportive. If that strikes you as being too accommodating to someone’s feelings—well, maybe personal relationships just aren’t for you.
    Fortunately, going deep doesn’t necessarily have to be so direct as asking “What is your deepest fantasy and wildest dream?” Even the techniques we just discussed about asking questions aren’t always applicable or helpful.
    As important as that step is, it can be exhausting. It can also be exhaustive—theoretically, once you’ve talked about events and subjects only pertinent to your own lives, you’ll run out of things to discover about yourself and the other person. There are only so many high school proms, parental arguments, complicated work scenarios, and family reunions you’ll get in one life. In the worst-case scenario, it will turn into a job interview gone awry.
    We are, of course, generally disposed to talk about ourselves and the things we’ve directly experienced or shared. But there’s a considerable amount of insight to be obtained by discussing subjects and events external to your life. Author Daniel Menaker straightforwardly calls this approach turning the conversation toward “third things—not me, not them, but something else.” It’s not about you or the other person in particular. It’s just about something external, even as benign as the news of the day or the types of ferns you are surrounded by. Call it upgraded small talk.
    Talking about these external topics serves as an inroad to discovering how somebody thinks and what they value. All this requires is that you ask how people feel about or would react to certain events, things, or situations.
    If you directly ask someone personal details about themselves, their answers are often flat or inadequate. Imagine someone (other than a therapist) asking, “Tell me about when you feel angry,” or “What do you believe in?” In addition to just sounding like left-field questions, they’re not likely to elicit very lucid responses. Some might find the inquiries a bit intrusive or nosy, especially in the early stages of a friendship or interaction.
    When you bring up things that are happening in the world, you actually get answers to those questions through others’ reactions to those external situations. Their opinions and feedback offer clues to the way they really are without feeling on-the-spot or awkward. Discussing external things can help you get a more complete picture of what makes up the person you’re with, and this is exceptionally helpful because there’s no limit to what you can talk about. For an example of the type of deeper information you can glean indirectly, consider asking someone, “Where do you get your news? What kind of publications do you read most of the time?”
    It’s an innocent question, and it’s something external. Yet you can learn much about someone’s views, preferences, values, and overall worldview by knowing their reference sources and preferred viewpoints. This is useful far beyond any political purpose—you immediately understand how someone likes to see the world when you know what media they tend to consume.

Instead of digging deep directly, which is often off-putting or awkward at best, you can obtain a deeper perspective by measuring people’s reactions to external things. You’ll often get a more honest answer, and you’ll learn more about them in the process.

Asking questions: not only does it take away your responsibility to talk all the time and help you find common ground with your conversational partner, but it also makes the other person feel like you care about them. Asking a question helps them see that their opinions and experiences matter to you, which makes them feel important. The secret sauce is simple; just ask questions and pay close attention to people’s answers.