Ask Your Kid ‘How Did You Think About It?’  

Parenting, I am learning, is like being the belayer to a roped rock climber — you have to know when to hold on tight and when to give some slack. (No, I’m not a rock climber myself, but I once took an intro class using a Groupon.)

You want to make sure your kids are safe and not making bonehead decisions, but you can’t follow them around throughout their lives, whispering, “Eh, you sure about that move there, buddy?” For them to reach new heights, sometimes you have to let go.

But how do you help them analyse situations and gain confidence in their choices along the way? I like this strategy from entrepreneur and investor Bryan Johnson, founder of Braintree, OS Fund and Kernel. When his children complete a new endeavour, he has them answer this question: “How did you think about it?”

In Tim Ferriss’ book Tools of Titans, Johnson explains:

So, we got on a four-wheeler 2 weeks ago — my 11- and 9-year-old and I — and I said, “OK, I am going to put your helmets on, I am going to give you a 2-minute lesson on how to go forward and how to go backwards, how to brake, I am going to give you some lessons — do not go into a ditch, do not go on a hillside that will turn you over, etc. — but I am expecting you now to go out for 5 minutes and come back safely, and tell me how you did it. What were your thought processes? How did you stay safe? What were the risks you took? But I want you to do it, and I’m not going with you.” …

They came back in one piece, and it was a good experience for them to tell me, “OK, Dad, this is how we looked at the risk, this is how we thought we might potentially get into a problem …” They [even ran into a tree] going slowly … but they talked about it, which I thought was really helpful.

As kids navigate their classrooms and social settings (and probably some new kid-slang that their friends picked up on Snapchat), there’s the tendency to want to jump in and guide their every move. But after you’ve gone over the basics, you’ll be teaching them more if you let them try things on their own and then reflect on them later.

Ask them how they succeeded, or why they think they stumbled. For instance, if your preschooler climbs to the top of the playground dome, instead of just saying “Great job,” you might ask her how she kept herself steady. Or when your usually-shy primary schooler announces he made a new friend, ask him how the conversation got started. Recounting how they thought through these scenarios will allow them to use those same decision-making skills in other situations.

You’re easing up on the rope. It’s scary and necessary.