A friend had recently committed to mentoring a teenage girl and asked me for help because she was having trouble getting into conversation with her new mentee. Her conventional approach to engaging young people—off-the-cuff questions that most often require only a yes-or-no answer—was failing. My friend was afraid she was not cut out for this mentoring thing. Here’s the note she wrote to me:

I recently started mentoring a 16-year-old girl. She is really quiet, really sweet. We have done some “activities” together—group volleyball, took her to Extreme Community Makeover on Saturday, and so on. But when I have just taken her out for ice cream or a picnic, there have been some quiet moments. I know her “file;” she’s living in a foster home and her foster mother is trying to adopt her and they have a good relationship. She’s been in foster care since she was nine and in this home for three years. She’s not seen her two younger siblings since she was nine. It’s all pretty heavy and I’m not a therapist! I guess I’m looking for some “safe” but nevertheless thought-provoking, somewhat probing, topics to discuss. I was hoping you might have guidance for me as I go into these out-of-my-comfort-zone waters! 

I could see my friend’s heart was “all-in,” but she felt lost in her pursuit of her. My response was to give her a strategy I use in the Jesus-Centered Ministry training I’ve been doing for two decades—it’s a more proactive, penetrating, and unlocking way to pursue people, plucked from the way Jesus pursued people. I call this the 6-Filter Questions strategy.

The 6-Filter Questions Strategy

1. Ask Questions That Surprise—The person is intrigued or grabbed or captured by the question. It means you include something in the question that takes people off guard—that makes them stop and think. Many discussion questions telegraph “the right answer.” They’re not really questions; they’re declarations masquerading as questions.

2. Ask Questions That Are Specific—Your question should focus on only one well-defined target. So many questions are really two questions in one. And many are way too broad in their focus; they look good on paper, but they are almost impossible to answer.

3. Ask Questions That Are Personal— This type of question asks for a personal response, not a general, rhetorical, or theoretical one. To answer requires people to share out of their heart, not just their head.

4. Ask more “Why?” questions and fewer “What?” questions. “Why?” questions force a kind of internal “chewing”—they naturally focus on the heart, because they target motivation. “What?” questions often focus on the obvious and can be answered in a simple way.

5. Ask questions that don’t have obvious answers and require more than a one-word answer. This is the most common mistake people make in asking questions. When you ask a question that has an obvious answer, or requires only a “yes” or “no” answer, you kill the conversation. Obvious-answer questions telegraph to people that you think they are incapable of thinking for themselves.

6. Ask Follow-Up Questions. Ask “Why?” questions to flesh out a deeper conversation. For example, when a person answers the question, “What bothers Jesus about the Pharisees,” with the answer “He hates hypocrisy,” follow up by asking “Why does He hate hypocrisy?” Keep asking “Why?” questions until you’ve drilled deeper into the heart of the issue—or the heart of Jesus. You can also ask: “Can you tell me more?” or “What brought you to that conclusion?” or “I wonder if…?”

Crafting Better Questions

When I thought about how I would use these filters to help my friend build her relationship with this teen, I sent her a few possibilities:

• Some people would love to win the lottery because they think that would solve all their problems. What do you think would “solve all your problems”? Why?
• What’s something about yourself that you secretly admire, and why?
• What qualities are common threads that run through your friends? Why are you drawn to the friends you have?
• When you’re really troubled or worried, what helps you feel at peace again? Explain why that’s true for you.

Practicing Persistence

Pursuing people using 6-Filter Questions feels like riding a bike for the first time. When we’re first learning to do it, we tend to over-think the “filters” and stumble around. But the more we practice, the more we can stop over-thinking our questions and have fun with them. 

Here’s Jesus teaching His disciples about the power of this kind of pursuit: “Suppose you went to a friend’s house at midnight, wanting to borrow three loaves of bread. You say to him, ‘A friend of mine has just arrived for a visit, and I have nothing for him to eat.’ And suppose he calls out from his bedroom, ‘Don’t bother me. The door is locked for the night, and my family and I are all in bed. I can’t help you.’ But I tell you this—though he won’t do it for friendship’s sake, if you keep knocking long enough, he will get up and give you whatever you need because of your shameless persistence” (Luke 11:5-8).

“Shameless persistence” is not what Jesus would do—it’s what Jesus does. And He’ll teach us to do it, if we ask Him for help. 

Editor’s Note: We hope our readers will be persistent in the practice of asking meaningful questions and building faithful, respectful relationships with young people. Enthusiastic consent is a key component of such conversations and relationships. Persistence in any form (emotional, conversational, or physical) past the point of consent is never appropriate.

Photo by  Maksim Chernyshev  on  Scopio.