A few weeks ago, I sat down next to an eighth grade boy. Wanting to engage him in conversation, I asked, “How’s school?”

I got a typical junior high boy answer: “Good.”

So I asked him a follow-up question. “What’s been good about it?”

To which he shrugged and said, “I don’t know.”


Rather than get frustrated, I switched tactics. “What’s been the worst part of school so far?”

Suddenly, this boy got animated. He proceeded to describe a class he hated and the reasons behind his distaste for it.

As a veteran youth worker, I like to think that I know how to engage youth in conversation – even the silent ones. And to some extent, I do.

Yet, the reality is that a good conversation with a student – especially junior high boys – usually only happens after a great deal of persistence.

I persist because I know that eventually, I can get someone talking.

But what about new adult leaders? Will they persist through the awkwardness of a conversation in order to get to the good stuff?

Not always.

Too often, adult leaders have only the first half of my conversation with a student. They ask several questions that elicit one-word responses or even worse, a shoulder shrug. Eventually, they get frustrated and find a way to exit the conversation, often concluding that a teen has no interest in talking to them.

Nothing could be further from the truth.

Teens want to talk to adults who will listen to them.

But we’re not their friends, so they’re not going to just open up and spill everything to us. In particular, this is true of boys, who especially in junior high tend to be less verbal than girls.

As a result, we need to teach leaders to ask good, open-ended questions in order to engage teens in meaningful conversation.

And as my earlier example shows, one of the best strategies for engaging teens is to ask them about the worst.

Tell me about the worst part of your day.

What’s your least favorite class and why?

Why does this work?

Because the reality is that often, teens don’t have a best part of their day – especially not on school days. They just have ordinary days, the details of which tend to blur together.

But when you ask about the worst part, teens can usually give you a concrete answer.


Because they remember that moment of their day.

They remember the unkind words they heard from a friend.

They remember the moment the teacher called on them and they didn’t know the answer to her question.

They remember forgetting their homework or failing their test.

They remember being laughed at.

They remember the fight they had with their mom or their best friend.

They remember those moments, even though they’re typically not the ones people ask about. So when you do, it shows that you care. As a result, youth are usually willing to trust you with their honest response. This invites you into their world and into a meaningful conversation that enables you to get to know them, their hearts, and their struggles. That, in turn, gives you the opportunity to be pastoral; To listen and to show teens love.

And that makes persisting through the awkward parts of a conversation with a teen worth every second.