Editor's Note: This article first appeared in Group Magazine--the world's most-read youth ministry resource. For more information, visit groupmagazine.com and get these great articles delivered right to your mailbox or iPad!

Awhile back a friend of mine asked me for help in pursuing the heart of a teenage girl who’s in the foster-care system—my friend had recently committed to mentoring her. Her normal conventional approach to engaging young people—off-the-cuff questions that most often require only a yes-or-no answer—was failing. Their times together were dominated by awkward silences. My friend was afraid she was not cut out for this mentoring thing. Here’s the note she wrote 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. The foster mom has shared some with me, too. She’s been in foster care since she was nine, and in this home for three years. I know some about her biological parents—she’s not seen two younger siblings since she was nine. She has never talked about any of this to me (I just know all of this from her file or her foster mom). Nor have I asked her about it; she’s young, she doesn’t know me. She sees a therapist; 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 unchartered, out-of-my-comfort-zone waters!

I could see my friend’s heart for this girl was “all-in,” but she felt lost in her pursuit of her. She was like the father in Mark 9 who brings his son, in the grip of an “unclean spirit,” to Jesus for healing. When he pleads with Jesus on behalf of his son, he says, “…IfYou can do anything, take pity on us and help us!” And Jesus responds: “‘If You can?’ All things are possible to him who believes.”And the man, desperate and humble, cries out, “I do believe; help my unbelief.” He’s saying, in effect, “My heart is all-in, but I need your help to know what to do!”

So my response to my friend’s desperate and humble “ask” centered around a three-filter strategy I use in my Jesus-Centered Ministry training track at our Simply Youth Ministry Conference—it’s a more proactive, penetrating, and unlocking way to pursue teenagers. This “can-opener” approach is plucked from the way that Jesus pursued people, over and over. The three filters for asking much, much better “pursuit” questions are:

1. Surprising—The young person doesn’t see the question coming.

2. Specific—It’s a question about one, specific thing—not multiple issues.

3. Personal—It asks for a personal—not a general, rhetorical, or theoretical—response.

So I thought about how I would apply these filters to my friend’s pursuit of this foster-care girl, then 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.

Pursuing teenagers using surprising, specific, and personal 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. Once you learn how to “ride this bike,” it will take you to places faster than you’ve ever been able to get to on foot—I mean, you will much more often unlock the authentic places in the lives of your kids.

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 forceful and leveraging and bold. It’s not what Jesus would do—it’s what Jesus does. And he’ll teach us to do it, if we ask him for help. ◊

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