“Stories and lessons from an unexpected journey in finance.”

I’ve negotiated deals worth hundreds of millions of dollars—M&A, financing rounds, complex vendor contracts. I’ve sat across from seasoned executives, investment bankers, and private equity partners.

But some of the toughest negotiators I’ve ever faced?

My kids.

No playbook. No term sheet. No artificial deadlines. Just relentless clarity of what they want—and an uncanny ability to push until they get it.

And over time, I realized something: the principles that make them effective aren’t childish… they’re fundamental.

1. They know their “why” cold.

Kids don’t negotiate for the sake of it. They want something specific—and they’re crystal clear about it. In business, we often lose that clarity. We negotiate points instead of outcomes. The best deals happen when you know exactly what matters—and what doesn’t.

2. They aren’t afraid of silence.

You’ve probably experienced it. You say “no”… and they just stare at you. No backtracking. No over-explaining. Just silence.

In negotiations, silence is uncomfortable—and powerful. The first person to fill it often gives something away.

3. They push boundaries—then recalibrate.

Kids will always ask for more than they expect to get. Not because they’re unrealistic, but because they’re testing the range. Too many executives negotiate inside self-imposed limits. If you don’t explore the edges, you’ll never know what’s possible.

4. They make it emotional—and that matters.

“Why can’t I stay up later?” isn’t a logical argument—it’s emotional. And while business negotiations should be grounded in facts, decisions are still made by people. Ignoring the human element is a mistake.

5. They don’t take it personally.

This one might be the most important. A “no” doesn’t end the conversation. It just resets it. Kids move on quickly, reframe, and try again. In business, we sometimes let ego or friction derail outcomes that are still achievable.

Here’s the irony: as we gain experience, we often unlearn these instincts. We become more polished—but sometimes less effective.

The next time you walk into a negotiation, don’t just rely on your models and talking points.

Channel a bit of that childlike clarity, persistence, and fearlessness.

You might be surprised how much better the outcome is.

And if nothing else… you’ll be better prepared for the next negotiation at home.

What’s the most unexpected place you’ve learned a negotiation lesson that actually changed how you approach deals?

#Negotiation #LeadershipLessons #TheAccidentalCFO #DealMaking #inersec