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How to Have Great One-on-Ones with Your Kids Every Time

We schedule one-on-ones for our kids, both with each other and also with April and me two times per week.

We post the schedule and do our best to keep up with this practice because it keeps all of our relationships rich and up-to-date.

I can feel the disconnection with my kids if it’s been a few weeks since our one-on-one.

During my Sabbath one-on-one every Saturday, I like to take one of my kids out for brunch.

Some parents are worried about awkward silences during these times or that they’ll just fill the space by talking themselves.

So let me share with you three simple tools that will help you have an amazing one-on-one with your kids.

Start out by asking your child, “What’s been on your mind?” Give them time to think about it and share. Ask them lots of questions about what they’re sharing.

No matter what they say or how long that conversation has gone, always follow-up this question: “Cool, what else has been on your mind?” Again, let them think about this, but often they will bring up something that is a layer deeper. Really take time to listen to them. Make one-on-ones a safe place for your kids to just process.

Once you’ve had that conversation and you still have time, bring out a stack of random questions.

For kids 5-12 I bring this box.

For teens I bring this box.

I know it might feel a little cheesy to have pre-planned questions, but I’ve had amazing conversations because of these questions.

It’s actually disarming for your kids to be asked random pre-planned questions because they aren’t worried by the thought of, “Wait, why are you asking me this?” 

If one of these questions leads to answers that surprise you ask good follow-up questions.

Great conversations come from great questions.

Here’s a picture of me and Elisa on a one-on-one a few weeks back. These are memories I will cherish for a long time, and the foundation we build during these times of deep connection I trust will last a lifetime.


This entry is a part of Jeremy’s Journal, a newsletter Jeremy sends out every Wednesday morning to encourage you on your parenting journey. You can sign up to get them every Wednesday here.

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