“Hey, howzit goin’?” “How are ya doing?” “What’s goin’ on, man?” Am I the only one who gets annoyed by these generic, un-heartfelt inquiries? It’s tried and true; superficial questions get superficial answers. Somehow I can’t hear Jesus casually asking the disciples or Pharisees, “How’s everybody doin’ today?”

Jesus often got into peoples’ heads and under their skin with the 73 questions He asked in the Gospel of Matthew alone. His questions either led up to something (“Who do people say the Son of Man is?”), revealed His character (thereby revealing God’s, “But what about you?…Who do you say I am?”), made people think (“Have you understood all these things?”), helped them process the principles He was teaching (“What do you think, Simon?”), or challenged their faith (“You of little faith, why do you doubt?”). If Jesus knew the answers to His questions, yet asked anyway, do we have good reasons to avoid question asking when we don’t know the answers?

Years ago, I began a personal study of communication, reading everything pertinent, paying attention to shows that highlighted communication techniques and taking mental notes about how certain people get the most relationship mileage in their ministries and personal friendships. Whether they taught it or I somehow caught it, I’ve learned that people who’ve mastered the fine art of question asking are more effective in communication all the way around.

Whether speaking in front of an audience, leading small groups, one-on-one, or (my personal favorite) bedtime snuggling with your kids, good question-asking skills and good questions themselves are worth learning. Even through e-mail, you can cyber-mentor if you know the right questions to ask. Students may communicate in writing what they feel too vulnerable to say in person. It may not be the optimum method of discipleship, but take what you can get until you can  coax them gently into talking to you.

In any given conversation, I ask people questions for one or all of the following reasons:
• I care and want to hear the answer.
• Often one needs to hear one’s own answer.
• Questions buy a little time to think things through in a serious conversation.
• Listening to the answer earns me the right to speak into the other person’s life.
• For the life of me, I can’t think of anything to say!

Youth mentor Jeanne Mayo used to warn her leadership core not to assume we knew the rest of the story when someone was talking—that even if we’d heard a similar story a dozen times; inevitably there might be a twist or detail that would open us up to the person, perhaps enabling us to be a greater help. Even when there’s no twist, Mayo told us to listen all the way through to the end anyway. The main reason I ask questions is to get inside the other person’s head and hear his or her heart. Who doesn’t want and need someone capable of that?

Anyone can ask a generic “How ya doin’?” but no matter how sincere you may be, questions like that are hit-and-miss. How often have you blown off that very inquiry thinking the inquirer didn’t really want to hear your answer? While there’s a risk to asking more personal questions—to you and the other person—once he or she knows you’ve really heard, trust tips the scale in the relationship and leads you into genuine friendship or at least healthy influence. It’s not about being simpatico; it’s about being real and by your gutsy questions, saying to the other person, “It’s safe for you to be real with me.”
Whether or not a student asks for advice, you can help her think through her issues by asking thought-provoking questions. While she may simply need an answer to a specific question, more often it’s critical for her sake that you help her be the one to come to biblical conclusions. I sometimes joke with youth leaders not to give away the end of the movie too quickly. We youth leaders are sometimes too quick to be answer machines, ask questions that make the big picture bigger, and underscore how their choices affect them and those around them. Once they’ve thought it through, the light bulb may or may not come on, but you’ve helped them think, either way.
Before I get to the great questions, let me offer some question-asking skills. Most people know the ones connected with that scholarly truism your mother used to quote about having one mouth and two ears. And don’t forget the simple-yet-bombastic, don’t ask yes-no questions or you’ll get yes-no answers. A “Zits” comic strip (Jerry Scott and Jim Borgman) shows Jeremy’s mom sensitively asking if something is bothering him. The second square shows Jeremy thinking his lengthy from-the-heart answer, but the final frame shows him verbalize, “No.” Mastering the fine art of question-asking in youth work, ministry, and relationships involves discernment, tact, and timing. Before you ask the other person questions, it’s helpful to ask yourself a few questions.
• Is this a good time and is this person ready to be quizzed?
• Are you the only person or the fifth person to ask key questions?
• Have you warmed up to him enough to delve a little deeper, or will he consider your great questions either prying or condescending?
• Have you given her a reason to believe you genuinely give a rip?
• What have you got to lose?
Once you’ve established a rapport in a setting comfortable for both of you, your self-examination shifts to listening skills. Have you ever noticed that it’s easier to look into someone’s eyes while they’re talking (no pressure), but unless it’s an inbuilt or trained habit, it’s difficult to maintain eye contact when you’re doing the talking (pressure)? Practice maintaining agreeable eye contact as you both listen and talk. Does your body language and facial expression intensify with the information that’s exchanged to the point of intimidating the other person? Relax. Or at least, look like it.
Below are questions for almost interactive scenarios, but they’re primarily geared toward one-on-one interaction—whether face-to-face, telephone, or cyberspace. The two questions I ask most (because when asked in a sincere tone, they’re effective, not to mention simple) are “Really?” and “Why?” During my study of Matthew, I found that the two questions Jesus asked most were variations of “What do you think?” and “What do you want?” Both reveal Jesus’ ability to be both compassionate and direct.
Here are other great questions, both general and specific, for encouraging, challenging, teaching, or just getting to know a student. Tweak to fit your personality and the person being asked:
• How will you prepare yourself for (a test, confrontation, college, a job interview, test results, etc.)?
• When I refer to (fill in the blank), what do you think I mean?
• What do you mean when you say, “(fill in the blank)”?
• If you had it your way, what would you do in this situation?
• Whom are you listening to?
• Do you feel comfortable with your decision?
• How important is this to you?
• How important do you think this is to your Parents? Friends? God?
• If you had an hour alone with God, how would you spend the time? (I asked my daughter this question when she was 10. Her reply: “We’d go to the mall and have a fruit-smoothie.”)
• If you heard someone else share what you just told me, how would you respond?
• What do you consider to be healthy boundaries?
• Who has had a positive influence on you? Why? What did he or she do specifically?
• What character traits do you possess that make you a positive influence?
• How do those qualities help you in relating to others?
• Who has had a negative influence on you? Why? What did he or she do or not do specifically?
• What character traits sometimes turn others off to you?
• What are areas you want to improve on and how have they kept you from relating to others?
• How does someone earn trust with you?
• How have you earned someone else’s trust?
• How’s your God-time?
• It’s obvious you’re sincere about your Christianity; is Jesus real to you at this point in your life?
• At what point in your life did God become real to you?
• What is God leading you to do?
• Looking back (on a specific situation), would you say/do anything different?
• What do you want most right now?
• What’s the worst-case scenario in this situation?
• If you were the other person, what would you do/say/think/feel?
• Have you talked with them (your mom/dad/boyfriend/friend) about it?
• Do you trust God with (fill in the blank)?
• What are you willing to change in order to bring change in yourself (or this situation/relationship)?
• After encouraging someone with advice on how to handle a certain situation, ask, “Is this fair advice?”
• In suggesting how to respond or handle a situation, ask, “Is this something you can see yourself saying/doing?” or “Do you feel like you can do this?”
• How did that affect the way you think of yourself? Feel about yourself?
• What choices are you making to remain pure in thought, in body, and in your heart?
• How can I help?
Here are some acceptance-and-trust responses to any number of statements a student might say:
• I love you, no matter what.
• I’m here for you.
• I may not agree with all your decisions, but I still love you, no matter what.
• Even if you don’t feel like talking about it, I want you to know I’ll be praying for you, and I’m all ears if you want to talk later.
• I trust you. I know you can make the right decision.
• I will challenge you…your thinking, especially the way you manage your emotions and relationships.