Apr 18

What’s Really Underneath the Conversation

Sam Bayer
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You may recognize Colden.

He’s the one I talked about in my TEDx talk. My then 13-year-old grandson who helped me realize that everything I thought I knew about conflict wasn’t just for the workplace. It was for everyday life.

He’s 16 now. And this time, the conflict wasn’t about a gaming computer.

1. THE SITUATION

This one had been building for a while.

About a year and a half ago, we started something together. Colden had already shown an interest in investing. He had even been making money trading football cards. So we decided to turn that curiosity into something more intentional.

We set up a Schwab investment account for him. His dad, Mike, became the custodian, and I worked with Colden on how to research companies, think about trends, and build a portfolio.

At the time, it felt like a win-win. Colden would learn. Mike would stay involved. And maybe it would even become something they could share together.

But that’s not how it unfolded.

Colden had been doing the work. He was researching companies, following trends, and thinking carefully about where to invest. Recently, he became especially interested in AI and wanted to make sure he was putting some of his money into companies in that space.

It was starting to pay off. He was gaining confidence.

But he couldn’t act on any of it without Mike.

And Mike just wasn’t engaging.

Every time Colden brought it up, the conversation either got pushed aside or turned into tension. The same pattern, over and over again.

2. THE TURN

At first, I stayed in coaching mode.

I worked with Colden on how to approach it differently. We talked about timing, tone, and curiosity. All the things that usually help move a conversation forward.

But nothing really changed.

After watching it play out a few times, it became clear this wasn’t about how the request was being made.

Something else was going on.

The more I paid attention, the clearer it became that this wasn’t about investing at all.

Mike operates at a very high level in his world. He is an elite athlete, a professional physical therapist, and a world class chef. If you ask him how to train for a sub-three-hour marathon, recover from an injury, or prepare an incredible meal, he can go deep for hours.

That is his domain.

But investing, technology, managing accounts… that’s a different world.

And when Colden kept coming back to it, I don’t think it felt like a simple request. It felt like being pulled into something unfamiliar, where he didn’t feel the same level of confidence or control.

And you could see it in how he responded.

Sometimes he avoided the conversation altogether. Other times he came back hard.

He moved back and forth between being a turtle and roaring like a lion.

That was the moment I realized this wasn’t something I could coach from the sidelines.

3. THE SHIFT

I needed to step in.

And I’ll be honest, that didn’t feel simple.

I care deeply about both of them. And I also had my own perspective on how this had been handled.

I had hoped to connect with Mike one-on-one first, just to understand how he was seeing it. But the conversation quickly became a three-way discussion.

That’s where it got tricky.

Because I knew something from experience. If my perspective showed up in the conversation, even a little, it would likely trigger Mike.

And once that happened, the conversation would go off track.

It would stop being about the problem and turn into something else entirely. Defensiveness. Frustration. Positions.

I’ve seen that pattern play out many times in my work.

This is a relationship that matters deeply to me. The last thing I wanted was to damage it by handling this poorly.

At the same time, avoiding the conversation wasn’t an option. Nothing was going to change on its own.

So the only real choice was to move forward.

But to do it carefully. To do it collaboratively.

And that meant preparing myself.

Not just what I wanted to say, but how I was going to show up.

I spent time with my AGENT AI Coach, working through the conversation ahead of time. Testing where I might get triggered. Noticing where he might get triggered. Thinking through how I would stay grounded if things got tense.

I also went back to a whiteboard explainer I had created on HEART and walked myself through it again.

https://www.youtube.com/watch?v=VGU8WohuVd4

I needed that reminder.

To slow down and really think about what might feel at risk for him.

Would he feel unheard?
Would he feel judged?
Would it feel like his role as a father was being stepped on?
Would it feel like he was losing control over something he was responsible for?

All of that felt possible.

And if any of that got triggered, it wouldn’t matter how logical or well-intentioned the conversation was.

We would lose the thread.

So I kept coming back to something simple.

Make sure he feels heard.
Make sure he feels respected.
Make sure he still feels like he has a role in this.

I also got clear on my own line.

If we couldn’t find a way forward, I was prepared to step in and become the custodian on the account. Not as a threat, just as an option.

4. AGENT IN ACTION

What made the difference

I spend a lot of time thinking about this work.

And even here, I could feel how easy it would have been to get this wrong.

This conversation only had a chance because I prepared for it. Not just what I wanted to say, but how I was going to show up.

That’s true whether you are experienced or not.

AWARE:
I recognized that this wasn’t about account transfers. It was a relationship dynamic that had gotten stuck.

GROUND:
I clarified what mattered to me and what I would do if we couldn’t resolve it.

EMPATHIZE:
I spent real time thinking about what might feel at risk for him, especially around being heard, respected, and staying in his role.

NEGOTIATE:
I approached the conversation as something we needed to figure out together, not something to push through.

TIE it all together:
The goal was a path forward that worked for Colden while still respecting Mike’s role and comfort.

Takeaway:
Important conversations don’t go well because you are experienced. They go well because you prepare.

5. PRACTICE FOR THE READER 🛠

Try this before your next conflict:

What am I carrying into this conversation that could trigger the other person?
What might feel at risk for them that I haven’t fully understood yet?
What would it look like to protect the relationship while still addressing the issue?

6. CLOSING REFLECTION

There is another layer to all of this that I’ve been thinking about.

As a parent, I know how hard it is to watch your child transition from child to adult. The way we interact with our kids has to evolve as they do, and that’s not always obvious in the moment.

For a child to take the lead in a conversation like this with a parent isn’t easy. It asks something of both sides. It asks the child to step forward, and it asks the parent, in some way, to recognize that their child is growing up.

That can trigger a lot.

I see that even in myself.

I still call my 45-year-old daughter Tovah by the nickname I gave her when she was two. She was an adult in a child’s body from very early on, and I was a big fan of The Wizard of Oz, so she became my Munchkin.

And while she will always be that two-year-old Munchkin to me, she is also one of the most inspirational and evolved adults I know.

Both of those things are true at the same time.