On Beautiful Conversations

And how to have more of them with adolescents

I’m not totally sure how the tradition of “Prompt Fest” started, but I got hooked on it right away.

It might have been when I was dating my wife and visiting with her extended family. This is a family that loves good conversation, but even so, there was a sense that we had more conversational potential in us. We could go deeper. At some point someone suggested we each write down one really good question — a “prompt” — put in a hat, and then everyone could draw one and answer it. With a few variations, that basic formula stuck, and now whenever the family gathers I must admit part of me is just waiting for the moment, usually during or after dinner, when someone says “is it time for Prompt Fest?”

It’s such a simple and light structure, but it lets us act on an important impulse — we all want to have deep conversations that connect us. Turns out that a little help goes a long way.

Here are some prompts that have come out of the hat:

• Which of the “seven deadly sins” do you relate to the most?

• If you found out you had one year to live, how would you spend your remaining time?

• If you could change one thing about how you were raised, what would it be?

And here’s a curious thing. I expected that the value of these would be learning about each other and feeling closer — and both are true — but I noticed another, quite striking result. When you speak a truth of yours into a group that listens deeply, you may end up hearing what you’re saying as if for the first time. I learned this some years ago when the prompt came up, “What is one dream for your life that you’ve held on to?”

I knew the answer instantly, because it was something I had been saying in my head for a long time. The words “I want to be a writer” came out of my mouth. Simple. But as I spoke it to the group, those words took on a sense of reality that they never had when bouncing around in my head. I could almost feel the second when “I want to be a writer” shifted from fantasy into shared reality. That odd clarity that it was going to happen, triggered by speaking it out, propelled me to start writing a book. And a few years later it did indeed exist, very much in paper-and-ink reality.

Where am I going with all this? I think we humans have a fundamental drive toward connection with others, but at the same time, we often lack the tools to act on it. As an adolescent, I wished someone would explain to me how to make friends and create good conversations, because I felt exceptionally unskilled, uninitiated. And now as an adult, I often hear a similar version of this from parents of adolescents, wishing for a way to have good conversations with their children.

The honest conversations you yearn for may just die on the vine if your first question is “how was your day?”

The challenge is, the honest conversation you yearn for may just die on the vine if your first question is “how was your day?”. If your child answers that one with depth, consider yourself lucky. But if they answer with “fine” or a mumble, welcome to the club. You’re ready for better questions. And there are many.

I’ll share a few, but first let me clarify one thing. Using a structure or strategy to prompt good conversation does not cheapen the conversation that follows in any way. Nor does it point to an embarrassing lack of skill on anyone’s part. Good conversational approaches are a skill, after all. The “Prompt Fest” takes place among a group of people who are already good at open, honest conversations, but even there, a little encouraging structure goes a long way. It gives permission.

So with that in mind, here are a few approaches I’ve enjoyed using for more meaningful conversations with adolescents. This is just the tip of the iceberg — please share your favorites in the comments!

1. Open vs Closed Questions. When I’m leading advisories of tweens and teens, I always tell them about the difference between Open and Closed Questions. I came across this concept from the educator and author Parker Palmer. Here’s an example — let’s say a peer tells you their birthday party is coming up this weekend. A closed question would be to ask, “how old will you be?” This likely leads to a one-word answer, a conversational dead-end. An open question might be to ask “what is the best birthday you’ve ever had?” That might lead somewhere interesting. Open questions are often a little surprising, and might lead the person receiving them to some new idea or insight, or to sharing more about themselves.

   

2. Avoid Summary Questions. Questions that ask someone to summarize their experience, while earnest and coming from a kind place, can often feel like a demand that has no real value to the question recipient. Of course, there’s nothing wrong with asking “how was your day” if you have a chatty child or student who is happy to talk you through it. But if that question isn’t landing, it may be because you’re asking them to do a lot of work — thinking about how their day was, filtering that for what they think you’re wanting to hear, and then regurgitating it all for you — likely at exactly the time when they’re tired and ready to move on from thinking about their day. We can do better than this!
   

3. Follow storylines. An alternative to the summary question, without needing to be a deep “prompt” in any way, is to ask for the next installment of a story. The kid who broke his arm on the playground — what happened next, how is he doing? The teacher who yelled at the class yesterday — did anything change after? Sometimes this is an easier entry point. It shows your interest by how you remember details (rather than asking for a broad summary), and taps into the natural human orientation toward stories.
   

4. Use the “Third Thing”. For adolescents and anyone with social anxiety, face-to-face, full-eye-contact conversations can be very taxing. An adolescent who is just becoming aware of how much is unspoken, thanks to their rapidly-improving social radar, is wondering what you’re really thinking, not necessarily trusting the words you say, and also wondering which of their own inner thoughts are leaking out through their facial expressions. That’s a lot of cognitive load. Many kids will be eager to wrap that kind of conversation up as soon as possible. So instead, try finding ways for conversations to be side-by-side rather than face-to-face. And better yet, side-by-side where you’re both focused on something you can talk about. This is the “third thing”, the shared point of focus between two people. It might be a puzzle you’re working on, a game you’re watching, a show, the view out the car window, etc. It allows silence to happen without being awkward, and often lets adolescents (and adults) speak more honestly.
   

5. Consider the Real Audience. You could sum up a lot of adolescent neuroscience by saying that if an adolescent knows a peer is nearby — or even might be nearby — then any response to a question you ask is spoken more with that peer in mind than to you. In other words, they may appear to be talking to you, but on some level they are choosing what they say based on the possibility that it’s being overheard by a peer. This phenomenon, part of the broader one known as the peer effect, stems from the way our brains become dramatically more socially oriented during adolescence. It’s almost as if peers are coming through in surround-sound and full living color, while an adult is in black-and-white, speaking through subtitles. This is not a choice that adolescents make, but a result of how their brains are changing.
   
   This leads to two viable strategies. You could try to work around the peer effect, say by finding ways to ask your good questions when there is no chance a peer is around. Let that anxiety or distraction be totally out of the picture. Or you can work with the peer effect, finding ways to prompt interesting conversation among peers, and then let yourself gradually fade into the background. I recently took my middle-school-aged daughter to her favorite taco place with one of her best friends, tossed a few open questions into the mix, and then tremendously enjoyed listening as they discussed their school life in far more detail than if they had been just responding to me. They were so engaged that I began to suspect they had forgotten I was there at some points, which I did not mind!

One last note. Lest we think that we, adults, are masters of conversation and have to drag adolescents into it, remember that extended, hilarious conversations with friends are one of the best parts of adolescence. In my day it was phone calls stretching on for hours, and now for my kids and students it’s FaceTime calls going on for hours (incidentally, I notice how often the FaceTime calls don’t actually feature face-to-face time — they’re often on in the background, avoiding the burden of major eye contact). Adolescents are good at this. Maybe we should trade tips, rather than be the instructors.

In fact, let’s tap the adolescent spirit of questioning adult behaviors for a moment. I’ve often talked with students about the strangeness of the American “how are you?” routine, in which we ask each other that question automatically, without the slightest expectation of an honest response. How odd is that? Pointing this out sometimes brings up a new possibility with my students — what if we subverted this strange habit, and, when we want to, asked how are you? like we meant it? What if we responded with the truth?

I think we want similar things, we humans. As far as I can tell, whether we’re 13 or 53, we want meaningful conversations with people we care about. We just need a little help sometimes. A Prompt Fest game might do it, or maybe a “third thing” to share, or that one open question that unlocks the conversation. All of this energized by our deep listening, creating that mysterious phenomenon in which the words you speak become more resonant once heard, and invite the next ones to follow.

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In other news…

• Argonaut: In the spirit of prompting good conversations, one of the most fun things I get to do is facilitate a handful of online advisory groups, with middle and high school students from around the world, through Argonaut. These groups are usually full, but I have a few spots for middle schoolers open in a new group starting next week, running on Tuesdays & Thursdays at 2pm Pacific / 5pm Eastern. Details here. My fellow facilitator and amazing human Annika Bhasavanich also has spaces in her online advisory group, meeting Tuesdays & Thursdays at 4pm Pacific / 7pm Eastern, here.

• Finding the Magic in Middle School: For those new to this newsletter, I wrote a book (after that Prompt Fest conversation I described above!) about how to tap into the potential of the middle school years, for parents and teachers. I deeply believe we can (and obviously should!) change the story of middle school. We need to stop telling middle schoolers, who are by definition people on a heroic adventure, that their best goal is to “just get through it.” Instead let’s set the conditions for them to have a beautiful, even magical, experience as they transform into complex, social, and far smarter humans. If this speaks to you, check the book out here.
  

• p.s. on Prompt Fests: In case it sounds like these conversations are just for adolescents and adults, one of my all-time favorite prompt fest moments involved my daughter when she was around 7 years old. She wandered into the couch area where the adults were prompt-ing, listened for a while, and then without missing a beat shared her thoughts on what makes good relationships, alongside everyone else. She had a wisdom and depth to her answer that shocked me in the best way. I was so glad that she got to witness a conversation like this and felt comfortable jumping in — and not for the last time realized how much I had underestimated her!