One-on-Ones with Teen Kids

If you’ve been around, you know that we really love to talk about how helpful it is to schedule one-on-ones with your kids especially as they get older, they get into close or into the teenage years. And I get a lot of questions as people begin to do this about, “Okay, how does that conversation go? How do you have a deep conversation?”

And so I really believe it’s a good idea to have some questions in your back pocket that you like to pull out during a one-on-one that just helps you get things going, helps you get into more heart to heart. And so there’s three questions that I love that are go-tos. With two of these, I’ve used a lot; and one that I just started using and it’s been awesome.

Okay, so the first one that I use a lot is, “What’s on your mind?” And that’s usually how I start. This was a question that was my biggest takeaway from the book, The Coaching Habit. He’s talking about this really in a business context. But he said when you’re in a coaching relationship this is probably his favorite question. He also likes to follow up this question with, “And what else?” Because he wants to… I love that. Because usually there’s a lot of things on their mind, but oftentimes the second thing they think about is actually a little deeper. And so it’s good to ask the question twice. “What’s on your mind. What else?”

The second question I like to ask is, “How’s your relationship with Mom? How’s your relationship with your brother? How’s your relationship with this friend?” Really get into the way that they’re relating to their friends, they’re relating to their siblings. That’s always an interesting conversation, something I like to check up on during the one-on-one, because that’s really an opportunity to coach.

Then the third one, which is that this new one which I really love is, “How are you doing, really?”


“How are you really doing?” It’s a really interesting question because people oftentimes are never asked this question this way, and it does something weird to you. When you’re asked… Just imagine a really close friend that you trust said, you’re sitting down, you got some time, maybe you’re having coffee and they’re like, “Okay, how are you doing really?” It’s interesting. That prompts you to go somewhere directly into your heart like, “Okay, I got to… “

And sometimes, usually the answer that you would answer that question, I know for me this is true, will probably surprise you. It pulls something out of you that’s deep. And again, that’s the whole point of a one-on-one, right, is to try to connect at the heart level. And so that kind of question I think really can help, help do that. But yeah, Jeff, what do you think about these questions?

Yeah. I love that and I totally agree. There’s something subtle about how when we ask questions it communicates more than the question, right? When sometimes, like you said that’s why the Coaching Habit “What’s on your mind?” is good, but that’s why he asked it a second time or “What else?” because that kind of assumes there’s more, right. And then same thing with, “How are you doing really” it kind of is already subtly saying like, “Oh yeah, we don’t need to do the small talk, the pleasantry.” It’s kind of assuming, like there is something you’re not saying, or there is a part that you can be close here with that you’re not close with everyone else or honest here.

There’s just the layers in questions that I think we have to be very aware of. And then how those translate, not just the teens but then I think also younger kids. You’re not going to get these deep complex answers, but I think how you ask questions to your kids really matters. And so just really, really pay attention to how you ask your kids about, “What are you feeling right now? What’s going on?” And like stuff like that. “And what are you thinking?”

I just love kind of asking questions. I think it does something to kids’ brains. Even in regards to like dangerous situations or whatever, I’m always mindful of like how am I asking these questions so that it’s not kind of projecting, maybe fear or whatever, but projecting with wisdom in questions I want them to internally ask, do you know what I mean?


Because at the end of the day, the questions you ask a lot of times turn into the questions they hear in their head the rest of their life. You know what I mean?


What do they say that the father’s voice has kind of the inner dialogue. I just think be mindful of that, and I think that’s an easy way actually to kind of really step into that.

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