Using OODA Loops to Iterate Conversations with Kids and Teens

The Dad Joke

Two of my great nephews were five at the time, and they and their families were visiting the grandparents. It was Nyles’s birthday, and Sam’s family bought him a new pair of Crocs, which he loved and wore everywhere. Sam thought it would be funny to take one of the shoes, and he ran around with Nyles chasing him with one shoe on and one shoe off. When they got to the pond, Sam threw the Croc as far as he could into the water. The fact that the pond was infested with alligators meant that there was no way to retrieve the shoe. All the adults, not to mention Nyles, got upset.

But me, I observed what happened, and oriented to the opinion that it was hilarious and a good foundation for a dad joke. That’s how I used OODA (observe, orient, decide and act) to turn it into a dad joke.

Next time I saw Sam, I acted. I initiated a conversation with him,

“Sam, people were really upset when you threw Nyles’s Croc into the water, weren’t they?”

“Yes,”

“Want to know why?”

“Yes, Mitch”

“Well, you threw the croc into an alligator pond. If you are gong to throw a croc, you have to find a crocodile pond first. Only throw Crocs into croc ponds.”

I observed the joke fell flat for two reasons. First, a five year old didn’t really appreciate the Croc-croc pun. Second, my niece, Sam’s mom, let me know in no uncertain terms, “Mitch, that’s not the lesson we want Sam learning from this.”

In the second OODA iteration, I oriented and came up with a new approach and decided to try it out with Bob, my brother-in-law and the boys’ grandfather.

“Bob, what do you get when you put a croc into an alligator pond?”

“What?”

Two unhappy six year olds.”

This also fell flat. Bob just went on to explain to me again why libertarians were better than Democrats or Republicans and why he had a hard time with either party.

Since then, I’ve OODA looped a few more times, but have still not been able to land a good dad joke from this incident.

I haven’t completely given up and my decision from my latest loop is that if I include it in this blog post, perhaps someone will read this, come up with the perfect joke, and send it to me.

Please?

Also, in the spirit of resilient MindShifting in complex situations, I am using the parallel strategy of continuing to work on this on my own.

OODAing Communications with Teenagers

I was always an active parent; I wanted to know what my kids were doing and thinking, how their days went, what homework they had, what they were learning, and so on.

That was a problem during their teen years.

“How was school today?”

“Okay”

“What did you do?”

“Stuff”

What did you learn?”

“Nothing”

There was some variation on that conversation every day. Every day I’d get frustrated and angry. They probably were frustrated and angry as well. We were both in scripts. We were in full blame mode and stuck in the same cycle.

This was before I knew about OODA loops.

If I were doing this today, instead of focusing on the failed communications and resorting to blame and anger, I’d use the iterative cycle of OODA loops to turn it into a game.

I’d try something with curiosity to see what happened, observe how it landed, and then orient to come up with alternatives to use next time, decide on some action, act with curiosity, and observe again.

One day I might try a general, “how was your day?”. Another time, I might try something more specific, “What did you cover in Math class?”. Then, perhaps, one day I’d line up 6 questions to answer in succession. Maybe give it a rest and try again in a few days. Maybe start with describing something interesting that happened to me and see if that spurred a conversation.

One of the things OODA does is that it focuses our attention on what we can try next rather than on the failure of what we just tried. Teenagers are only difficult for about five years. I had two children who overlapped and so that gave me about eight years to play the OODA iteration game and try different approaches.

I still may not have ever succeeded in opening up, although I might have, but it would have been a lot more fun and I’m sure I would have improved my communication skills.

In both of these examples, using OODA focuses attention on observing, adjusting, and acting rather than judging and reacting emotionally. If you want more on using OODA to iterate effectively at work, school, family, or leisure, use the search bar on the top of this page to look up other articles on OODA loops.

This post is an excerpt of MindShifting: Resilient Mindsets for Long-Term Success, which is coming out in April, 2027.

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I’m Mitch…the mind behind MindShifting

For over four decades, I’ve been at the intersection of education, technology, and learning transformation, helping individuals, educators, and organizations rethink how we learn, teach, and grow.

I created MindShifting to help people break free from self-imposed limitations, reframe challenges, and unlock new possibilities. Whether in education, business, or personal growth, the ability to shift perspectives is the key to success, resilience, and innovation.

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